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Shenai, Zhiping Xu and Yang Zhao",authors:[{id:"113078",title:"Prof.",name:"Yang",middleName:null,surname:"Zhao",fullName:"Yang Zhao",slug:"yang-zhao"}]},{id:"30423",title:"Methodology for Optimization of Polymer Blends Composition",slug:"methodology-for-optimization-of-polymer-blends-composition",signatures:"Alessandra Martins Coelho, Vania Vieira Estrela Joaquim Teixeira de Assis and Gil de Carvalho",authors:[{id:"113021",title:"Dr.",name:"Alessandra",middleName:"Martins",surname:"Coelho",fullName:"Alessandra Coelho",slug:"alessandra-coelho"},{id:"115680",title:"Dr.",name:"Vania",middleName:"V.",surname:"Estrela",fullName:"Vania Estrela",slug:"vania-estrela"},{id:"148104",title:"Prof.",name:"Joaquim Teixeira",middleName:null,surname:"De Assis",fullName:"Joaquim Teixeira De Assis",slug:"joaquim-teixeira-de-assis"},{id:"148105",title:"Prof.",name:"Gil",middleName:null,surname:"De Carvalho",fullName:"Gil De Carvalho",slug:"gil-de-carvalho"}]},{id:"30424",title:"Applications of PCA to the Monitoring of Hydrocarbon Content in Marine Sediments by Means of Gas Chromatographic Measurements",slug:"applications-of-pca-to-the-monitoring-of-hydrocarbon-content-in-marine-sediments-by-means-of-gas-chr",signatures:"Mauro Mecozzi, Marco Pietroletti, Federico Oteri and Rossella Di Mento",authors:[{id:"114883",title:"Dr.",name:"Mauro",middleName:null,surname:"Mecozzi",fullName:"Mauro Mecozzi",slug:"mauro-mecozzi"},{id:"115922",title:"Dr.",name:"Marco",middleName:null,surname:"Pietroletti",fullName:"Marco Pietroletti",slug:"marco-pietroletti"},{id:"115923",title:"Dr.",name:"Federico",middleName:null,surname:"Oteri",fullName:"Federico Oteri",slug:"federico-oteri"},{id:"115924",title:"Dr.",name:"Rossella",middleName:null,surname:"Di Mento",fullName:"Rossella Di Mento",slug:"rossella-di-mento"}]},{id:"30425",title:"Application of Principal Component Analysis in Surface Water Quality Monitoring",slug:"application-of-principal-component-analysis-in-surface-water-quality-monitoring",signatures:"Yared Kassahun Kebede and Tesfu Kebedee",authors:[{id:"115360",title:"M.Sc.",name:"Yared",middleName:"Kassahun",surname:"Kebede",fullName:"Yared Kebede",slug:"yared-kebede"},{id:"150317",title:"MSc.",name:"Tesfu",middleName:null,surname:"Kebede",fullName:"Tesfu Kebede",slug:"tesfu-kebede"}]},{id:"30426",title:"EM-Based Mixture Models Applied to Video Event Detection",slug:"em-based-mixture-models-applied-to-video-event-detection",signatures:"Alessandra Martins Coelho and Vania Vieira Estrela",authors:[{id:"113021",title:"Dr.",name:"Alessandra",middleName:"Martins",surname:"Coelho",fullName:"Alessandra Coelho",slug:"alessandra-coelho"},{id:"115680",title:"Dr.",name:"Vania",middleName:"V.",surname:"Estrela",fullName:"Vania Estrela",slug:"vania-estrela"}]},{id:"30427",title:"Principal Component Analysis in the Development of Optical and Imaging Spectroscopic Inspections for Agricultural / Food Safety and Quality",slug:"principal-component-analysis-in-the-development-of-optical-and-imaging-spectroscopic-inspections-for",signatures:"Yongliang Liu",authors:[{id:"115612",title:"Dr.",name:"Yongliang",middleName:null,surname:"Liu",fullName:"Yongliang Liu",slug:"yongliang-liu"}]},{id:"30428",title:"Application of Principal Components Regression for Analysis of X-Ray Diffraction Images of Wood",slug:"application-of-principal-components-regression-for-analysis-of-x-ray-diffraction-images-of-wood",signatures:"Joshua C. Bowden and Robert Evans",authors:[{id:"117200",title:"Dr.",name:"Joshua",middleName:null,surname:"Bowden",fullName:"Joshua Bowden",slug:"joshua-bowden"},{id:"117205",title:"Dr.",name:"Robert",middleName:null,surname:"Evans",fullName:"Robert Evans",slug:"robert-evans"}]},{id:"30429",title:"Principal Component Analysis in Industrial Colour Coating Formulations",slug:"principal-component-analysis-in-industrial-color-coating-formulations",signatures:"José M. Medina-Ruiz",authors:[{id:"115796",title:"Dr.",name:"Jose",middleName:"M",surname:"Medina-Ruiz",fullName:"Jose Medina-Ruiz",slug:"jose-medina-ruiz"}]},{id:"30430",title:"Improving the Knowledge of Climatic Variability Patterns Using Spatio-Temporal Principal Component Analysis",slug:"improving-the-knowledge-of-climatic-variability-patterns-using-spatio-temporal-principal-component-a",signatures:"Sílvia Antunes, Oliveira Pires and Alfredo Rocha",authors:[{id:"100098",title:"Dr.",name:"Alfredo",middleName:null,surname:"Rocha",fullName:"Alfredo Rocha",slug:"alfredo-rocha"},{id:"117291",title:"Dr.",name:"Sílvia",middleName:null,surname:"Antunes",fullName:"Sílvia Antunes",slug:"silvia-antunes"},{id:"117315",title:"Dr.",name:"Oliveira",middleName:null,surname:"Pires",fullName:"Oliveira Pires",slug:"oliveira-pires"}]},{id:"30431",title:"Automatic Target Recognition Based on SAR Images and Two-Stage 2DPCA Features",slug:"automatic-target-recognition-based-on-sar-images-and-two-stage-2dpca-features",signatures:"Liping Hu, Hongwei Liu and Hongcheng Yin",authors:[{id:"117576",title:"Dr.",name:"Liping",middleName:null,surname:"Hu",fullName:"Liping Hu",slug:"liping-hu"}]}]}]},onlineFirst:{chapter:{type:"chapter",id:"69071",title:"Synthesis of Quinazoline and Quinazolinone Derivatives",doi:"10.5772/intechopen.89180",slug:"synthesis-of-quinazoline-and-quinazolinone-derivatives",body:'\nQuinazoline (1,3-diazanaphthalene or 5,6-benzopyrimidine) and 4(3H)-quinazolinone derivatives have a great interest in organic synthesis and medicinal chemistry fields as they possess a broad range of pharmacological activities. They exhibit antimicrobial [1], antimalarial [2], antioxidant [3], anti-inflammatory [4], anticonvulsant [5], antihypertensive [6], antidiabetic [7], and antitumor activities [8, 9, 10].
\nMany quinazolinone derivatives occurred naturally in various classes of the plant kingdom, microorganisms, and different animals (\nFigure 1\n). The first discovery of quinazolinone alkaloid is
Structure of different quinazolinone alkaloids.
Quinazoline is a heterocyclic compound of two fused six-membered simple aromatic rings—benzene and pyrimidine ring. It is a yellow-colored compound, found usually in crystalline form. Its oxo-derivative (quinazolinone) is classified into three types according to the position and number of carbonyl group: 2(1H)quinazolinones, 4(3H)quinazolinones, and 2,4(1H,3H)quinazolinedione (\nFigure 2\n).
\nStructure of quinazoline and different quinazolinone compounds.
Quinazoline is a compound made up of two fused six-membered simple aromatic rings—benzene and pyrimidine ring. The properties of the pyrimidine ring were affected by the presence of fused benzene ring. The two nitrogen atoms are not equivalent, and the marked polarization of the 3,4-double bond is reflected in the reactions of quinazoline. The properties of quinazoline derivatives depend on the following three factors:
The nature of the substituents
The presence of substituent whether they are in the pyrimidine ring or in the benzene ring
The presence of conjugation in the pyrimidine ring
The first synthesized quinazoline in laboratory was achieved by Gabriel in 1903 [12]. Most of quinazoline derivatives are stable in cold acidic or basic medium but can be destroyed at high temperature and undergo ring opening reaction, affording O-aminobenzaldehyde, ammonia, and formic acid. Quinazoline derivative can be easily oxidized in acidic medium at room temperature to give 3,4-dihydro-4-oxo quinazoline, while in alkaline medium using potassium permanganate will afford 3,4-dihydro-6 4-oxo quinazoline (cf. \nFigure 3\n).
\nOxidation reaction of quinazoline at different medium.
The spectroscopic analysis of some synthesized quinazoline and quinazolinone derivatives was studied to investigate their structures including infrared, mass spectroscopy, 1HNMR, and elemental analysis. The resulted data could be taken as standard for the new synthesized quinazoline analogue [13].
\nQuinazoline derivatives found to give mainly three absorption bands in IR spectra: 1478–1517, 1566–1581, and 1612–1628 cm−1; these represented bands are correlated to C▬N, C=C, and C=N groups, while quinazolinone compounds showed 1680–1700 and 1640–1660 cm−1 corresponding to C=O and C=N groups [13, 14].
\n\n
The 1HNMR spectra of quinazoline and quinazolinone derivatives are different from each other according to the presence of acidic proton and its position in the presented compound. In general the 1HNMR spectrum of the main quinazoline (I) represents multiple signals in the aromatic region δ 7–8 and two singlet signals for the two CH=N protons at δ 9–9.5 ppm, while quinazolinone (II) will show also signals of aromatic protons in the same region as well as one singlet signal for CH=N proton and one broad singlet signal at the down-field region for the NH proton at δ 12–13 ppm [13, 14].
\nOn the other hand, the 13C NMR spectrum for quinazoline and quinazolinone derivatives is nearly the same, as it shows signals at δ 100–160 ppm region.
\nThe synthesis of various quinazoline compounds is largely based on the substitution patterns of the 1,3-diazine moiety of the system. The first quinazoline derivative (2-cyano-3,4-dihydro-4-oxoquinazoline) was synthesized in 1869 by the reaction of cyanogens with anthranilic acid [15]. Many years later quinazoline was obtained by decarboxylation of the 2-carboxy derivative (quinazolinone) which can be synthesized more easily by a different method.
\nFrom anthranilic acid and formamide.
\n\n
From the reaction of o-amino benzoic acid with amine in the presence of phosphorus trichloride in toluene.
\n\n
Various quinazoline and quinazolinone derivatives can be synthesized from the reaction of benzoxazinone and different amine compounds in different media.
\nWhen ammonium hydroxide reacted with benzoxazinone (1) over 1–3 h, it produced anthranilamides (2) which cyclizes to 4-quinazolones (3) under thermal conditions (240–280°C) or on heating with acetic anhydride [16, 17].
\n\n
It was stated by several authors that 2-substituted benzoxazinone reacted easily with primary aromatic amines, giving the corresponding quinazolones (4) [18].
\n\n
On the other hand, reaction of benzoxazinone (5) with o-phenylenediamine gave quinazolinone derivative (6) or the fused quinazoline derivative (7) according to the reaction medium [19].
\n\n
It was reported that benzoxazinone (8) reacted with hydrazine hydrate in ethanol and has the corresponding quinazolinone (9), while carrying out the same reaction in boiling acetic acid glacial afforded the fused quinazoline (10) [13].
\n\n
Treatment of 2-substituted-3,1-benzoxazin-4-ones (11) with semicarbazide hydrochloride in dry pyridine is a good way to construct a third heterocyclic ring condensed with quinazoline (12) [18].
\n\n
The reaction of benzooxazinone (8) with 2-benzamido-3-phenylacrylohydrazide (13) glacial acetic acid in the presence of fused sodium acetate gave quinazoline derivative (14). In contrast, their reaction in pyridine afforded pyrazoloquinazoline derivative (15) [13].
\n\n
Reaction of benzoxazinone (8) with cyanoacetohydrazide gave the corresponding cyano quinazolinone (16) which was reacted with different nucleophiles to give fused quinazoline and annulated quinazolinone derivatives (17–19) [13].
\n\n
It was also reported that refluxing an equimolar amount of the benzoxazinone (8) with thiocarbonohydrazide in ethanol and in the presence of few drops of glacial acetic acid furnished quinazolinone (20) in the two isomers of thione and thiol form [13].
\n\n
Isobutyrylanilides with urethane and phosphorus pentoxide in xylene gave 2-propyl- and 2-isopropyl-3,4-dihydro-4-oxoquinazolines.
\nReaction of 2-aminobenzylamine with butyrolactone further condensed with benzaldehyde afforded 3-(2-chlorobenzylidene)-1,2,3,9-tetrahydropyrrolo-2-quinazoline.
\nAs we mentioned above, the important biological activity of quinazoline and quinazolinone skeletons in various fields depends mainly on the substituents of quinazoline compounds. Different substituted quinazoline compounds are found to be active as antihypertensive, antineoplastic, antidepressant, and antipsychotic, and others are effective against analgesic, antipsychotic, antiarrhythmic, cancer, and other activities [20, 21, 22].
\nIt was reported that 3-substituted quinazolin-4(3H)-ones and 3,4-dihydroquinazolin-2-(1H)-one derivatives possess broad spectrum antitumor activities toward different cell (\nFigure 4\n) [23].
\nAnti-tumor quinazolinone derivatives.
Also, different quinazoline derivatives containing thiosemicarbazide moiety possess antitumor activity (\nFigure 5\n) [24].
\nQuinazoline derivatives bearing thiosemicarbazide possess anti-tumor activity.
It was reported that some novel substituted iodoquinazoline derivatives possess remarkable activity toward Gram-negative bacteria
Quinazoline derivatives with antibacterial activity.
A series of Schiff bases of some 2-phenyl quinazoline-4(3)H-one derivatives have shown great activity as antiviral agents (\nFigure 7\n) [26].
\nDifferent schiff base of quinazolinone with antiviral activity.
The (S)-4-aminoquinazoline alcohols performed great antimutagenic activity when tested by using
Antimutagenic activity of amino quinazoline derivative.
Some novel thiazoloquinazoline derivatives are investigated for antioxidant activity by DPPH radical assay, nitric oxide scavenging activity, and hydrogen peroxide scavenging activity and possess high potent antioxidant activity (\nFigure 9\n) [28].
\nAntioxidant activity of different quinazoline.
Quinazoline and quinazolinone compounds which have a lot of considerable pharmacological interests can be synthesized by different methods, and the most attractive method was carried out starting from benzoxazinone derivatives.
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I am also a member of the team in charge for the supervision of Ph.D. students in the fields of development of silicon based planar waveguide sensor devices, study of inelastic electron tunnelling in planar tunnelling nanostructures for sensing applications and development of organotellurium(IV) compounds for semiconductor applications. I am a specialist in data analysis techniques and nanosurface structure. I have served as the editor for many books, been a member of the editorial board in science journals, have published many papers and hold many patents.",institutionString:null,institution:{name:"Sheffield Hallam University",country:{name:"United Kingdom"}}},{id:"54525",title:"Prof.",name:"Abdul Latif",middleName:null,surname:"Ahmad",slug:"abdul-latif-ahmad",fullName:"Abdul Latif Ahmad",position:null,profilePictureURL:"//cdnintech.com/web/frontend/www/assets/author.svg",biography:null,institutionString:null,institution:null},{id:"20567",title:"Prof.",name:"Ado",middleName:null,surname:"Jorio",slug:"ado-jorio",fullName:"Ado Jorio",position:null,profilePictureURL:"//cdnintech.com/web/frontend/www/assets/author.svg",biography:null,institutionString:null,institution:{name:"Universidade Federal de Minas Gerais",country:{name:"Brazil"}}},{id:"47940",title:"Dr.",name:"Alberto",middleName:null,surname:"Mantovani",slug:"alberto-mantovani",fullName:"Alberto Mantovani",position:null,profilePictureURL:"//cdnintech.com/web/frontend/www/assets/author.svg",biography:null,institutionString:null,institution:null},{id:"12392",title:"Mr.",name:"Alex",middleName:null,surname:"Lazinica",slug:"alex-lazinica",fullName:"Alex Lazinica",position:null,profilePictureURL:"https://mts.intechopen.com/storage/users/12392/images/7282_n.png",biography:"Alex Lazinica is the founder and CEO of IntechOpen. After obtaining a Master's degree in Mechanical Engineering, he continued his PhD studies in Robotics at the Vienna University of Technology. Here he worked as a robotic researcher with the university's Intelligent Manufacturing Systems Group as well as a guest researcher at various European universities, including the Swiss Federal Institute of Technology Lausanne (EPFL). During this time he published more than 20 scientific papers, gave presentations, served as a reviewer for major robotic journals and conferences and most importantly he co-founded and built the International Journal of Advanced Robotic Systems- world's first Open Access journal in the field of robotics. Starting this journal was a pivotal point in his career, since it was a pathway to founding IntechOpen - Open Access publisher focused on addressing academic researchers needs. Alex is a personification of IntechOpen key values being trusted, open and entrepreneurial. Today his focus is on defining the growth and development strategy for the company.",institutionString:null,institution:{name:"TU Wien",country:{name:"Austria"}}},{id:"19816",title:"Prof.",name:"Alexander",middleName:null,surname:"Kokorin",slug:"alexander-kokorin",fullName:"Alexander Kokorin",position:null,profilePictureURL:"https://mts.intechopen.com/storage/users/19816/images/1607_n.jpg",biography:"Alexander I. Kokorin: born: 1947, Moscow; DSc., PhD; Principal Research Fellow (Research Professor) of Department of Kinetics and Catalysis, N. Semenov Institute of Chemical Physics, Russian Academy of Sciences, Moscow.\r\nArea of research interests: physical chemistry of complex-organized molecular and nanosized systems, including polymer-metal complexes; the surface of doped oxide semiconductors. He is an expert in structural, absorptive, catalytic and photocatalytic properties, in structural organization and dynamic features of ionic liquids, in magnetic interactions between paramagnetic centers. The author or co-author of 3 books, over 200 articles and reviews in scientific journals and books. He is an actual member of the International EPR/ESR Society, European Society on Quantum Solar Energy Conversion, Moscow House of Scientists, of the Board of Moscow Physical Society.",institutionString:null,institution:{name:"Semenov Institute of Chemical Physics",country:{name:"Russia"}}},{id:"62389",title:"PhD.",name:"Ali Demir",middleName:null,surname:"Sezer",slug:"ali-demir-sezer",fullName:"Ali Demir Sezer",position:null,profilePictureURL:"https://mts.intechopen.com/storage/users/62389/images/3413_n.jpg",biography:"Dr. Ali Demir Sezer has a Ph.D. from Pharmaceutical Biotechnology at the Faculty of Pharmacy, University of Marmara (Turkey). He is the member of many Pharmaceutical Associations and acts as a reviewer of scientific journals and European projects under different research areas such as: drug delivery systems, nanotechnology and pharmaceutical biotechnology. Dr. Sezer is the author of many scientific publications in peer-reviewed journals and poster communications. 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