Type III secretory toxins in P. aeruginosa.
\\n\\n
Dr. Pletser’s experience includes 30 years of working with the European Space Agency as a Senior Physicist/Engineer and coordinating their parabolic flight campaigns, and he is the Guinness World Record holder for the most number of aircraft flown (12) in parabolas, personally logging more than 7,300 parabolas.
\\n\\nSeeing the 5,000th book published makes us at the same time proud, happy, humble, and grateful. This is a great opportunity to stop and celebrate what we have done so far, but is also an opportunity to engage even more, grow, and succeed. It wouldn't be possible to get here without the synergy of team members’ hard work and authors and editors who devote time and their expertise into Open Access book publishing with us.
\\n\\nOver these years, we have gone from pioneering the scientific Open Access book publishing field to being the world’s largest Open Access book publisher. Nonetheless, our vision has remained the same: to meet the challenges of making relevant knowledge available to the worldwide community under the Open Access model.
\\n\\nWe are excited about the present, and we look forward to sharing many more successes in the future.
\\n\\nThank you all for being part of the journey. 5,000 times thank you!
\\n\\nNow with 5,000 titles available Open Access, which one will you read next?
\\n\\nRead, share and download for free: https://www.intechopen.com/books
\\n\\n\\n\\n
\\n"}]',published:!0,mainMedia:null},components:[{type:"htmlEditorComponent",content:'
Preparation of Space Experiments edited by international leading expert Dr. Vladimir Pletser, Director of Space Training Operations at Blue Abyss is the 5,000th Open Access book published by IntechOpen and our milestone publication!
\n\n"This book presents some of the current trends in space microgravity research. The eleven chapters introduce various facets of space research in physical sciences, human physiology and technology developed using the microgravity environment not only to improve our fundamental understanding in these domains but also to adapt this new knowledge for application on earth." says the editor. Listen what else Dr. Pletser has to say...
\n\n\n\nDr. Pletser’s experience includes 30 years of working with the European Space Agency as a Senior Physicist/Engineer and coordinating their parabolic flight campaigns, and he is the Guinness World Record holder for the most number of aircraft flown (12) in parabolas, personally logging more than 7,300 parabolas.
\n\nSeeing the 5,000th book published makes us at the same time proud, happy, humble, and grateful. This is a great opportunity to stop and celebrate what we have done so far, but is also an opportunity to engage even more, grow, and succeed. It wouldn't be possible to get here without the synergy of team members’ hard work and authors and editors who devote time and their expertise into Open Access book publishing with us.
\n\nOver these years, we have gone from pioneering the scientific Open Access book publishing field to being the world’s largest Open Access book publisher. Nonetheless, our vision has remained the same: to meet the challenges of making relevant knowledge available to the worldwide community under the Open Access model.
\n\nWe are excited about the present, and we look forward to sharing many more successes in the future.
\n\nThank you all for being part of the journey. 5,000 times thank you!
\n\nNow with 5,000 titles available Open Access, which one will you read next?
\n\nRead, share and download for free: https://www.intechopen.com/books
\n\n\n\n
\n'}],latestNews:[{slug:"intechopen-partners-with-ehs-for-digital-advertising-representation-20210416",title:"IntechOpen Partners with EHS for Digital Advertising Representation"},{slug:"intechopen-signs-new-contract-with-cepiec-china-for-distribution-of-open-access-books-20210319",title:"IntechOpen Signs New Contract with CEPIEC, China for Distribution of Open Access Books"},{slug:"150-million-downloads-and-counting-20210316",title:"150 Million Downloads and Counting"},{slug:"intechopen-secures-indefinite-content-preservation-with-clockss-20210309",title:"IntechOpen Secures Indefinite Content Preservation with CLOCKSS"},{slug:"intechopen-expands-to-all-global-amazon-channels-with-full-catalog-of-books-20210308",title:"IntechOpen Expands to All Global Amazon Channels with Full Catalog of Books"},{slug:"stanford-university-identifies-top-2-scientists-over-1-000-are-intechopen-authors-and-editors-20210122",title:"Stanford University Identifies Top 2% Scientists, Over 1,000 are IntechOpen Authors and Editors"},{slug:"intechopen-authors-included-in-the-highly-cited-researchers-list-for-2020-20210121",title:"IntechOpen Authors Included in the Highly Cited Researchers List for 2020"},{slug:"intechopen-maintains-position-as-the-world-s-largest-oa-book-publisher-20201218",title:"IntechOpen Maintains Position as the World’s Largest OA Book Publisher"}]},book:{item:{type:"book",id:"996",leadTitle:null,fullTitle:"An International Perspective on Topics in Sports Medicine and Sports Injury",title:"An International Perspective on Topics in Sports Medicine and Sports Injury",subtitle:null,reviewType:"peer-reviewed",abstract:"For the past two decades, Sports Medicine has been a burgeoning science in the USA and Western Europe. Great strides have been made in understanding the basic physiology of exercise, energy consumption and the mechanisms of sports injury. Additionally, through advances in minimally invasive surgical treatment and physical rehabilitation, athletes have been returning to sports quicker and at higher levels after injury. This book contains new information from basic scientists on the physiology of exercise and sports performance, updates on medical diseases treated in athletes and excellent summaries of treatment options for common sports-related injuries to the skeletal system.",isbn:null,printIsbn:"978-953-51-0005-8",pdfIsbn:"978-953-51-6793-8",doi:"10.5772/1503",price:159,priceEur:175,priceUsd:205,slug:"an-international-perspective-on-topics-in-sports-medicine-and-sports-injury",numberOfPages:546,isOpenForSubmission:!1,isInWos:1,hash:"ebee9fb7ab59a8696147c49b4cf6c72e",bookSignature:"Kenneth R. 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Propagation of multidrug‐resistant
The pathogenesis responsible for mortality in
Toxin secretion systems in Gram‐negative bacteria. In the types I and II secretion systems, bacteria secrete toxins into the extracellular space (left side of figure). As one example, secreted toxins are captured by surface receptors on the eukaryotic cell membrane and are then transferred to the cytosol. In the types III and IV secretion systems, bacteria secrete toxins directly into the cytosol of target eukaryotic cells through their secretion apparatus (right side of the figure). The mechanism whereby the secreted toxins are transferred to the eukaryotic cell cytosol is called translocation.
In this review, we summarize the TTSS of
In most acute clinical manifestations of
In the mid‐1990s, researchers investigating
The whole genome sequencing project by the
The PAO1 reference strain genome and its pathogenic gene configuration. The
The clinical isolate UCBPP‐PA14 is cytotoxic and is similar to the laboratory strain PA103 UCBPP‐PA14 that has the TTS phenotype ExoS−ExoT+ExoU+ExoY−, whereas invasive PAO1 is ExoS+ExoT+ExoU−ExoY+ [16, 20]. Therefore, genomic analysis of UCBPP‐PA14 was conducted to identify their phenotypic differences. As a result, two pathogenicity islands that do not exist in PAO1 were discovered in the UCBPP‐PA14 genome [27]. Thereafter, researchers found that clinical strains containing
The TTSS is composed of the following: (1) secretion apparatus (injectisome), (2) translocators, (3) a set of secreted toxins, and (4) regulatory components [28]. In the
Genomic structure of the exoenzyme S regulon. The type III secretion regulatory region (25.5 kb), found as a gene cluster, was named the exoenzyme S regulon. The exoenzyme S regulon comprises five operons, including 36 genes for transcription (
Type III secretion regulation in
Toxins | Size (kDa) | Enzymatic activity | Action |
---|---|---|---|
ExoS | 49 | FAS‐dependent ADP‐ribosyltransferase | Antiphagocytosis, inhibition of endocytosis |
ExoT | 53 | Small GTPase activating protein activity | Inhibition of tissue repair |
ExoU | 74 | Phospholipase A2 | Cytotoxin, lipid degradation |
ExoY | 42 | Adenylate cyclase | Edema formation, anti‐inflammatory |
Type III secretory toxins in P. aeruginosa.
One operon in the exoenzyme S regulon, called
The type III secretory apparatus of
Historically,
In the late 1970s,
ExoS and ExoT are two immunologically indistinguishable proteins that co‐fractionate with exoenzyme S activity [14]. ExoS and ExoT encode proteins of 457 and 453 amino acids, respectively, and share 75% amino acid identity. ExoT possesses approximately 0.2% of the ADP‐ribosyltransferase activity of ExoS [14, 15]. ExoT diminishes motility of macrophages and phagocytosis, at least in part through disrupting the eukaryotic cellular actin cytoskeleton, and also blocks wound healing [43, 44]. The ExoS carboxyl terminal catalyzes transfer of the ADP‐ribose moiety of nicotinamide adenine dinucleotide to a number of different proteins, including the intermediate filament protein, vimentin [45–47].
The amino terminal domains of ExoS and ExoT have been characterized as GAPs of Rho GTPases [48]. The Rho GAP activity of ExoS stimulates reorganization of the actin cytoskeleton by inhibiting Rac and Cdc42, and induces formation of actin stress fibers by inhibiting Rho [49]. These domains, which include catalytic arginines, share sequence homology with not only
A specific isogenic mutant of the cytotoxic
ExoU contains a potato patatin‐like phospholipase A (PLA) domain [17]. Patatin is a member of a multigene family of vacuolar storage glycoproteins with lipid acyl hydrolase and acyl transferase activities. Alignment of ExoU, potato patatin, and human PLA2 shows three highly conserved regions in the ExoU amino acid sequence as follows [17]: (1) a glycine‐rich nucleotide binding motif, GXGXXG/A (position 111–116 in ExoU); (2) a serine‐hydrolase motif, which includes a serine active site for cPLA2, GXSXG/S (position 140–144 in ExoU); and (3) an active site motif containing aspartate for cPLA2, DGG/A (position 344–347 in ExoU) (Figure 6).
Enzymatic activity and consensus motifs in ExoU.
Site‐directional mutations in the predicted catalytic site of ExoU cause a loss of lysophospholipase A activity [52]. Airspace instillation of virulent
ExoY has adenylate cyclase activity and is secreted by the TTS mechanism [12]. The primary ExoY sequence shares homology with sequences of the extracellular adenylate cyclases of
Respiratory infections with
In our epidemiological study that analyzed clinical isolates, there was a subset of isolates that displayed the TTS phenotype ExoS−ExoU− with extensive drug‐resistant characteristics [63]. Most of these isolates were from chronic infections in patients with CF. Therefore, clinical isolates of
Type III secretory toxin phenotypes in
Phenotypic variation in
Year | Author | Reference | CF clinical isolates, | TTSS secretion (+), | Exoenzyme genotype, | Exoenzyme phenotype, | ||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|
S | T | Y | U | |||||||||
2000 | Dacheux et al. | [69] | 29 | 8 (27.5%) | 28 | 28 | 28 | 3 | 8 (28.6) | 8 (28.6) | NA | 0 (0) |
2004 | Jain et al. | [61] | 235 (CI, children) | 40 (18%) | NA | NA | NA | NA | 35 (88) | 40 (100) | NA | 2 (5) |
200 (CI, adults) | 8 (4%) | 8 (100) | 8 (100) | NA | 0 (0) | |||||||
35 (NI) | 17(49%) | 17 (100) | 17 (100) | NA | 0 (0) | |||||||
2005 | Lee et al. | [68] | 7 | 5 (71.4%) (initial) | 7 | NA | NA | 0 | 5 (71.4) | NA | NA | 0 (0) |
3 (42.8%) (subsequent) | 6 | NA | NA | 1 | 2 (28.6) | NA | NA | 1 (14.3) | ||||
2007 | Wareham et al. | [70] | 75 | 39 (52%) | 66 | 75 | 74 | 12 | NA | NA | NA | 9 (75) |
2008 | Jain et al. | [67] | 1299 (CI, children) | 29.1% | NA | NA | NA | NA | NA | NA | NA | NA |
1217 (CI, adult) | 11.5% | |||||||||||
135 (NI) | 45.2% | |||||||||||
2013 | Hu et al. | [71] | 52 (initial) | 43 (82.7%) | 44 | NA | NA | 8 | 36 (82) | NA | NA | 7 (88) |
40 (subsequent) | 26 (65%) | 33 | NA | NA | 7 | 19 (58) | NA | NA | 7 (100) |
Studies on the relationship between cystic fibrosis and type III secretion in
Most studies have reported that the proportion of
Comparative genomics on the reference PAO1 strain and isolates from patients with CF are on‐going. In 2003, two comparative studies between CF isolates and PAO1 were reported. These studies demonstrated that clinical strains do not express TTSS, whereas most of them that are isolated from chronic infections possess this gene cluster [74, 75]. Additionally, these studies show that 10% of genes in CF isolates do not exist in the PAO1 genome, and half of them are newly identified genes.
Recent reports have indicated that the combination of carbapenem and fluoroquinolone resistance and the presence of the gene encoding the TTSS ExoU effector in
Recent outbreaks of XDR‐PA are threatening to increase colonization by MDR‐PA in immunocompromised patients because efficacious antimicrobial choices are extremely limited. Therefore, this situation requires development of new prophylactic or therapeutic strategies that do not rely on conventional antimicrobial agents [86, 87].
The first experimental trial on immunotherapy against the TTSS of
The mechanism responsible for the positive effect of the polyclonal anti‐PcrV antibodies, in terms of whether the effect depends on the Fc‐portion of the antibody, was investigated. The anti‐PcrV polyclonal antibody F(ab)′2 was tested in a rabbit model, and the same effect as whole IgG was confirmed [90]. This finding strongly suggests that the prophylactic and therapeutic effects of anti‐PcrV polyclonal antibodies are derived by blocking the action involved in the pathogenicity of the antigen. Monoclonal antibody screening on normal mouse hybridomas was then performed and the clone mAb166 was discovered as the strongest TTSS blocker [40]. The clone mAb166 displayed equivalent therapeutic and prophylactic effects to those of the anti‐PcrV polyclonal antibody [40, 91, 92]. The mAb166 Fab fragment also conferred the same therapeutic effect as the original whole IgG in
Active immunization with PcrV was examined in immunocompromised mice that were pretreated with cyclophosphamide [97]. Cyclophosphamide treatment induced immunosuppression in the mice, decreased immunity against
The intravenous immunoglobulin (IVIG) was recently shown to confer significant protection against lethal infection with virulent
In this review, we summarize the current status of research on the pathogenesis and treatment of
This work was supported by the Japan Society for the Promotion of Science, Grants‐in‐Aid for Scientific Research (KAKENHI Nos. 24390403, 26670791, and 15H05008), and The Ministry of Education, Culture, Sports, Science and Technology, Japan to Teiji Sawa.
CF | cystic fibrosis |
GAP | GTPase‐activating protein |
IVIG | intravenous immunoglobulin |
MDR‐PA | multidrug‐resistant Pseudomonas aeruginosa |
PAPI‐2 | P. aeruginosa pathogenicity island‐2 |
PLA | Phospholipase A |
TTS | Type III secretory |
TTSS | Type III secretion system |
XDR‐PA | extensively drug‐resistant P. aeruginosa |
The great advantage of DMF, DMA and other
DMF and DMA as a synthon for the various reactions.
A non-exhaustive seminal review by Muzart [1], highlighted different roles of DMF inorganic synthesis covered literature up to 2009, another comprehensive review by Ding and Jiao appeared in 2012 [12] which covered aspects of DMF as a multipurpose precursor in various reactions. Further, specialized review by Batra et al. [13], and other reviews dealing with recent applications of DMF and DMA as a reagent [14] and triple role of DMF as a catalyst, reagent and stabilizer also appeared [15].
In this book chapter we summarized developments on applications of DMF and DMA in reactions such as amination (R-NMe2) [16], formylation (R-CHO) [17, 18], as a single carbon source (R-C), methylene group (R-CH2) [19], carbonylation (R-CO), as well as newer reactions such as amidoalkylation (-CH2N(CH3)-C(〓O)CH3-R) [20], metal catalyzed aminocarbonylation (R-CONMe2) [21], cyanation (R-CN) [22, 23], and formation heterocycles, took place during the past few decades and up to October 2019. Heterocycles are important compounds finding excellent applications as useful materials and medicinally important compounds. Thus unlike other reviews appeared on this subject [1, 12, 13, 14, 15], we provided special emphasis on synthesis of heterocyclic compounds and reactions involving DMF and DMA. Thus, first part of this book chapter will cover synthesis of construction of cyclic system, especially heterocycles, the next part will cover the formation of open chain compounds. Although DMF can serve as a reagent in organic reactions such as Friedel-Crafts [24] and Vilsmeier-Haack [25] reactions the actual reagent is derivative of DMF, hence we did not cover such subjects. We hope this book chapter will stimulate further research interest on the application of DMF and DMA in organic synthesis.
Guan and co-workers reported synthesis of symmetrical pyridines from ketoxime carboxylates using DMF as a one carbon source in the presence of ruthenium catalyst and NaHSO3 as an additive (Figure 2). A series of ketoxime acetates
Pyridine ring formation by DMF using Ru-catalyzed cyclization of aryl ethyl ketoxime acetates.
A possible mechanism for the reaction was proposed. Oxidation of DMF by Ru(II) gives an iminium species
Su et al., reported cyclisation of 4-(phenylamino)-2
DMF as a methine source in pyridine ring formation via cyclization of 4-(phenylamino)-2H-chromen-2-ones.
The reaction proceeded smoothly with electron-donating and electron-withdrawing substituents on the aniline ring and the expected products were obtained in good yields. A plausible mechanism was proposed by the author in. Initially, DMF is converted into iminium ion
In 2015, Deng and co-workers reported the Ru catalyzed multi-component reaction of acetophenones
Ru-catalyzed cyclization of acetophenones with NH4OAc.
In this reaction DMF, in the presence of Ru/O2 catalyst, acted as a single carbon source. For better understanding of reaction mechanism, several control experiments were carried out [28] (Figure 4). Acetophenone was converted into a methyl ketene intermediate
Jiang and co-workers developed the first example of employing
DMF as a dual synthon in synthesis of pyrimidine carboxamide.
The desired product was obtained in good yield under the optimal reaction condition Pd(TFA)2 (5 mol%), Xantphos (5 mol%) and 70% TBHP (3.0 equiv) in 1.0 mL DMF at 120°C. Benzamidine salts containing electron-releasing or electron-withdrawing group on the benzene ring gave their desired product in moderate to good yield. Addition of radical scavenger, such as TEMPO (2,2,6,6-tetramethylpiperidine-1-oxyl), BHT (2,6-di-tert-butyl-4-methylphenol), and DPE (1,1-diphenylethylene) led to no desired product formation, which indicates the radical pathway is involved in this transformation [29].
Xiong et al., reported a general and highly selective method for annulation of amidines
DMF as a one carbon source in Cu-catalyzed annulations of amidines.
This is an efficient copper catalyzed synthesis of quinazolines
In 2017, Fan et al., reported an efficient method for the synthesis of pyrimidines
DMF in multicomponent synthesis of pyrimidines from amidines.
In 2016, Das et al., reported Pd/Ag catalyzed direct carbonylation of sp2C-H bonds of
Pd/Ag catalyzed pyrido carbonylation of
The reaction was examined using different metal catalyst systems such as Pd-Ag, Cu-Ag, Co-Ag, Ni-Ag and finally Pd-Ag catalytic system was found to be suitable for this transformation [32]. When labeled DMF (CO18) was used as the solvent it has been found that product found not to contain O18. From these results, it can be concluded that incorporated carbonyl group is coming from the methyl group of DMF. Reaction under argon instead of oxygen lead to the poor yield, which indicates “O” atom is coming from oxygen environment.
In 2015, Wu et al., reported C-H bond activation of arenes
DMF as CO source in Pd-catalyzed carbonylation.
The reaction was optimized using different oxidant and catalysts under different temperature condition and the desired product was obtained in good yield in the presence of Pd(OAc)2-K2S2O8 and DMF/TFA solvent system at 140°C under O2 atmosphere. When the reaction was conducted with 13CO-labeled DMF (
In 2017, Chang and coworkers reported metal, ligand free, base promoted cascade reaction of DMF with
Synthesis of dihydropyrrolizino[3,2-
Deng et al., reported a metal free approach for the synthesis of 3-acylindoles
Formation of 3-acylindoles from 2-alkenylanilines.
To prove the synthetic utility of this transformation gram scale experiment was conducted under optimized condition, wherein the yield of the corresponding product decreased slightly. Control experiments revealed that DMF acts as carbon source and O2 is the source of the oxygen. When deuterium labeled DMF was used as solvent, the labeled product was observed. Meantime, to probe the source oxygen atom in the final product a reaction has implemented with 18O-DMF and only non-labeled product was obtained. Thus, author justified that O2 is the source of the oxygen atom in the final product [35].
Liu et al., developed a methodology for the synthesis of
The cyclization of 2-aminothiophenol with DMF.
To understand the role of CO2 in this reaction, isotopic labeling reaction were carried out using 13CO2, the non-labeled benzothiazole was observed in excellent yield [36]. When this cyclization reaction was carried out using d7-DMF instead of DMF, deuterated benzothiazole was obtained. This experiment revealed that DMF served as the formylating reagent CO2 as the promoter.
Yadav et al. developed a cost effective synthetic protocol with 100% conversion of o-nitroaniline to benzimidazole using DMF as in-situ source of dimethylamine and CO. Herein, DMF undergoes water gas shift reaction in the presence of CuFe2O4 as catalyst to produce hydrogen (Figure 13). It mainly involves two steps the reduction of o-nitroaniline
One-pot synthesis of benzimidazole.
A possible mechanism was proposed by author. Thermal degradation of DMF in the presence of water provides CO, which undergoes water gas shift reaction in the presence of catalyst to release hydrogen gas. This H2 reduces nitro group to form amine group. The formation of o-phenylenediamine was confirmed with the help of GC-MS and HPLC analysis and compared with standard samples. Further, formylation of one of the amine groups took place in the presence CO, then intramolecular cyclisation takes place to give benzimidazole.
Ohshita et al. developed method for the synthesis of coumarins
Synthesis of different coumarin derivatives.
Yamamoto and coworkers synthesized exocyclicdiene-type α,β,γ,δ-unsaturated amides
Hydrocarbamoylative cyclization of 1,6-diynes with DMF.
Having covered literature on construction of cyclic system, especially heterocycles using DMF or DMA as a next part we cover literature on the formation of open chain compounds.
An excellent method to access benzamides
Metal catalyzed aminocarbonylation of aryl halides using DMF.
Similarly, Indolese et al. reported aminocarbonylation of aryl halides
Furthermore, Lee and co-workers demonstrated the same reaction between aryl bromides/iodides
Wang et al., reported a metal-free radical amidation of thiazoles and oxazoles
DMF as a source for aminocarbonylation of azoles.
Wang et al., demonstrated direct amidation of alcohols
DMF as a source for aminocarbonylation of alcohol and amines.
Feng and coworkers proposed green protocol for the synthesis of α-ketoamides
DMF as aminocarbonylation source in synthesis of α-ketoamides.
Similarly, the synthesis of α-ketoamides
In 2016, Xiao and his team developed a simple and efficient technique for the synthesis of amides
DMF in Ru-catalyzed amidation of carboxylic acids.
Similarly, Tortoioli and co-workers demonstrated one-pot synthesis of dialkyl amides under metal free condition through the reaction between benzoic acid and DMF in presence of propyl phosphonic anhydride (T3P) with acid additives [49]. This mild method has been applied to the synthesis of dihydrofolate reductase inhibitor, triazinate (Figure 21).
Amidation of benzoic acid with DMF.
Bhat et al. reported direct carbamoylation of heterocycles
DMF as source for aminocarbonylation of quinoline.
Bhisma et al. gave an efficient copper catalyzed synthesis of phenol carbamates
Carbamate synthesis from phenols and formamides.
Phan and coworkers under oxidative condition synthesized organic carbamates
CDC reaction of phenol with DMF.
Yuan et al., synthesized S-phenyldialkylthiocarbamate
Synthesis of S-phenyldialkylthiocarbamate.
Kamal and coworkers proposed an efficient and greener methodology for the synthesis of selenocarbamates
Oxidative C-Se coupling of formamides and diselenides.
Reddy and coworkers synthesized chiral symmetrical urea derivatives
Synthesis of chiral symmetrical urea derivatives from DMF.
Chang et al., reported that benzoxazoles
Amidation of benzoxazole using Ag2CO3 catalyst.
Interestingly, this method is also suitable for the optically active formamide, the desired product was obtained in better yield without racimization [56].
Li et al., gave a method for the synthesis of 2-aminoazole derivatives
Similarly, Yu et al., developed a decarbonylative coupling between azoles and formamides. The iron catalyzed direct C-H amination of azoles at C2 took place in the presence of formamides and amines as nitrogen source (Figure 29). Easily accessible iron (II) salts acted as Lewis acid which activated the C2 position of benzoxaoles
Amidation of benzoxazole using Cu or Fe catalyst.
Peng and coworkers developed a facile and efficient route for one pot synthesis of 2-acyl-4-(dimethylamino)-quinazoline
Direct amination of 2-aryl quinazoline-4(3
Eycken et al. demonstrated a convenient microwave-assisted de-sulfitative dimethylamination of 5-chloro-3-(phenylsulfanyl)-2-pyrazinones
De-sulfitative amination of 2(1H) pyrazinone.
Hongting et al. developed an efficient, atom-economic and eco-friendly approach for synthesizing enamines
Intermolecular hydroamination of activated alkynes.
Li et al., developed hypervalent iodine mediated reaction between carboxylic acids
Synthesis of O-aroyl-
Liang and coworkers gave a simple and efficient one-pot multicomponent reaction of chalcones
Synthesis of γ-ketoamide.
Xia and coworkers proposed a simple and green approach for the synthesis of sulfonamides through t-BuOK mediated direct S-N bond formation from sodium sulfinates
Synthesis of sulfonamides using DMF as a amine source.
Gong et al., reported a base-promoted amination of aromatic halides
A base-promoted amination of aromatic halides.
In recent past several methods were developed for using DMF as a methylene source.
Wang et al., developed a new method for the synthesis of vinylquinolines
Synthesis of vinyl quinolones using DMF with iron catalyst.
Qian Xu and coworkers developed an eco-friendly iron-catalyzed benzylic vinylation which transfers the carbon atom in
DMA or DMF Synthesis of vinyl 2-vinylazaarenes.
Miura et al., demonstrated an effective way for α-methylenation of benzyl pyridines
α-methylenation of benzylpyridines using DMA.
Li et al., developed an iron-catalyzed α-methylenation of aryl ketones
α-methylenation of acetophenones.
In 2019, Wang et al., reported a one-pot procedure for the synthesis of 3-indolyl-3-methyl oxindoles
α-methylenation of 2-arylacetamides with DMF.
Liu and coworkers reported a method for the synthesis of diindolylmethane
Cu-catalyzed synthesis of diindolylmethane.
In 2014, Xue and co-workers developed methylation of ketones
Rh-catalyzed direct methylation and hydrogenation of ketones using DMF.
A possible mechanism was proposed as shown in Figure 44. Initially, persulfate oxidizes DMF to give a reactive iminium intermediate. The intermediate
A possible mechanism for methylation and hydrogenation of ketone.
Li et al., reported direct oxidative thiolation of sp3 C-H bond next to a nitrogen atom
Thiolation of sp3 C-H bond next to a nitrogen atom.
In this oxidative thiolation reaction, thiol group was successfully coupled with sp3 C-H bond of
It is noteworthy that various benzothiazole and a fipronil analogs could also be synthesized through this methodology (Figure 46) [73].
TBHP-mediated synthesis of benzothiazoles.
Stephenson et al., developed Friedel-Craft amidoalkylation of alcohols and electron rich arenes as potent nucleophile with alkyl amides
FC amidoalkylation using alkyl amides.
In this method inexpensive and efficient persulfate was used as oxidant for the construction of C-O and C-C bonds. Most of the time, photo catalysis provided better selectivity and good yields for the Friedel-Crafts reactions as compared with the thermolytic reaction conditions [74].
Li et al., gave a transition metal-free method for amidation of sp3 C-H bond in amides through cross dehydrogenative coupling process by using iodide anion as catalyst and TBHP as oxidant (Figure 48). It proceeds through free radical intermediate which is confirmed by TEMPO and the products has an potential bioactivity
Amidoalkylation under metal free condition using DMA.
In 2017, Chen and coworkers demonstrated copper-catalyzed C-N bond formation of triazoles
Copper-catalyzed C-N bond formation of triazoles.
Zhu and Co-Workers discovered a new methodology for the synthesis of 2-amidoalkylated benzothiazole and 3-amidoalkyl substituted indolinone derivatives using
Amidoalkylation of benzothiazoles with DMA.
It is interesting to note that dialkylamides could undergo reaction to generate cycano group. In 2011 Ding et al., reported a novel and another kind of pathway to produce the aryl nitriles
Similarly, in 2015, Chen and co-workers developed a selective copper-catalyzed C3-cyanation of indole under an oxygen atmosphere with DMF as a safe CN source and as a solvent (Figure 51) [79].
Cyanation of indole and benzofuran.
Wang et al., demonstrated a copper catalyzed cyanation of indoles
Cyanation of indole with DMF.
Chang et al., reported a new approach for the synthesis of Aryl nitriles
Cyanation of arylhalides and plausible mechanism.
Ushijima et al., reported the synthesis of aromatic nitriles
Conversion of electron-rich aromatics into aromatic nitriles.
A possible mechanism for this reaction was given in Figure 54. When treated with ammonia, the iminium salt can be transformed into the aromatic imine. Then molecular iodine serves as an oxidizing agent and reacts with the aromatic imine to provide the corresponding aromatic
However, the need of highly electron-rich aromatics in the formation of aromatic
Conversion of electron-rich aromatics into aromatic nitriles and plausible mechanism.
Followed by the treatment with molecular iodine in aqueous ammonia. Similarly, the same author reported synthesis of aryl nitriles from aryl bromides in the presence of Mg [84].
Further, dialkylamides were also used as a formylation source. Wang et al., transformylated different amines, primary or secondary, aromatic or alkyl cyclic or linear, mono- or di-amine with DMF as formylation reagent to obtain corresponding formamides
The best part about the CeO2 catalyst is the strong basicity and medium water-tolerant acidity (Figure 56) [85].
Transformylation of amines with DMF.
In 2017, Jagtap and coworkers reported highly efficient Ni(II) metal complex catalyzing
Formylation and acylation of amines using
The importance of this reactions are cost-effective, easily available starting material, high reactivity and inertness toward air and water [86].
Larsen et al., developed a convenient method for the synthesis of α,β-acetylenic aldehydes
Synthesis of α,β-acetylenic aldehydes.
Jeon and co-workers reported methyl benzoate
Dialkylamides have ability to acts as hydrogen source and it has been used in several functional group transformations. It is advantageous to use hydrogen gas
Hua et al. reported triruthenium dodecacarbonyl [Ru3(CO)12] catalyzed stereo divergent semi-hydrogenation of diaryl alkynes
Stereodivergent [Ru3(CO)12] catalyzed semihydrogenation of diaryl alkynes.
Chan et al., reported a hydrogenation reaction catalyzed by cobalt porphyrins which hydrogenated C-C bond of [2.2] paracyclophane
DMF as hydrogenating reagent for benzylic positions.
In 2017, Liu and coworkers synthesized α-arylketothioamides
Synthesis of α-arylketothioamides.
Carbonylation is another important reaction in which the poisonous “CO” gas is generated from dialkylamides in the presence of suitable catalysts. Thus carbonylation reaction using dialkylamides is highly advantageous.
Gunanathan and coworkers developed a new mode of bond activation which is used effectively for the synthesis of simple and functionalized symmetrical and unsymmetrical urea derivatives from amines using DMF as CO source (Figure 63). Activation of N-H bond of amines by Ruthenium pincer complex and after that CO insertion from DMF with the liberation of hydrogen. Nucleophilicity of amines is essential for urea formation. The significance of this reaction occurs in an open condition, it avoids side products, doesn’t require any pressure setup [92].
Carbonylation of amines with DMF.
Furthermore, Chen and co-workers reported a unique and highly effective method for the formation of imidazolinones
Formation of complicated imidazolinones with DMF.
It is noteworthy that, the utilization of DMF as a precursor in heterocyclic synthesis was important development in the field of synthetic organic chemistry. With advent of new reagents, catalytic systems and need for development of efficient synthetic protocols it could be predicted that dialkyl amides will continue to find new applications in organic synthesis. So far dialkyl amides have been mainly utilized as a synthon through mono functionalization of one of the groups. Further, there is a lot of scope for its utilization as a difuctionalization, for example, alkyl group attached to carbonyl and nitrogen in DMA could be functionalized at both the ends simultaneously. Dialkyl amides due to low cost, ready availability and flexibility in reactivity, will continue to gain attention of synthetic chemists as a synthon, ligand, dehydrating agent and solvent. We appreciate all of the authors cited herein for their tremendous contributions that have developed this field. We hope that it is sufficiently impressive and thorough that it will increase the interest on organic chemistry and will initiate further developments in the applications of DMF/DMA beyond being just a polar solvent, because it can be used as substrates in several reactions such as formylation, amination, amidoalkylation, aminocarbonylation, amidation, and cyanation and it has been achieved under both metal-catalyzed and metal-free conditions. We believe this book chapter will make it easy for the synthetic chemists and invoke an idea about utility of dialkyl amides for some novel functional group transformations.
P.S thanks to UGC-RFSMS, New Delhi for the award of the fellowship for Ph.D.
The authors declare no conflict of interest.
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",metaTitle:"Waiver Policy",metaDescription:"We feel that financial barriers should never prevent researchers from publishing their research. With the need to make scientific research more publically available and support the benefits of Open Access, more institutions and funders have dedicated funds to assist their faculty members and researchers cover the APCs associated with publishing in Open Access. Below we have outlined several options available to secure financing for your Open Access publication.",metaKeywords:null,canonicalURL:"/page/waiver-policy",contentRaw:'[{"type":"htmlEditorComponent","content":"At IntechOpen, the majority of OAPFs are paid by an Author’s institution or funding agency - Institutions (73%) vs. Authors (23%).
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\n\nThe first step in obtaining funds for your Open Access publication begins with your institution or library. IntechOpen’s publishing standards align with most institutional funding programs. Our advice is to petition your institution for help in financing your Open Access publication.
\n\nHowever, as Open Access becomes a more commonly used publishing option for the dissemination of scientific and scholarly content, in addition to institutions, there are a growing number of funders who allow the use of grants for covering OA publication costs, or have established separate funds for the same purpose.
\n\nPlease consult our Open Access Funding page to explore some of these funding opportunities and learn more about how you could finance your IntechOpen publication. Keep in mind that this list is not definitive, and while we are constantly updating and informing our Authors of new funding opportunities, we recommend that you always check with your institution first.
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\n\nOur mission is to support Authors in publishing their research and making an impact within the scientific community. Currently, 14% of Authors receive full waivers and 6% receive partial waivers.
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