Abstract
Considering the great prevalence of heterocyclic compounds in the core structure of numerous natural products, synthetic drug candidates, active pharmaceutical ingredients, and also in optoelectronic materials; tremendous efforts have been dedicated toward their synthesis and functionalization. But, the exploitation of hazardous, volatile organic solvents and toxic reagents caused disadvantageous effects on the atom economy and eco-friendly nature of the chemical transformation. Therefore, developing chemical processes providing easy access to complex target molecules by avoiding the utilization of hazardous solvents and reagents for making our environment toxic-free is of increasing significance for chemists in both academia and industry. The synergic combination of the features of mechanochemical activation as alternative energy input with the efficiency associated with small organic molecules that can catalyze chemical reactions is predominantly relevant to fulfill the goal of green and sustainable chemistry. This chapter is dedicated to providing a critical overview on the application of mechanochemical techniques for the synthesis of five- and six-membered heterocycles, as well as complex-fused heterocycles and spiro-heterocycles under organocatalytic conditions.
Keywords
- mechanochemistry
- bioactive heterocycles
- organocatalysis
- ball-milling
- grinding method
1. Introduction
Heterocyclic compounds comprise a broad range of structural motifs ubiquitously found in the architecture of numerous natural products and active pharmaceutical ingredients [1, 2, 3]. They are frequently existed in the markedly available drug candidates, fine chemicals and play a fundamental role in medicinal chemistry as a consequence of their outstanding biological activities, such as anticancer, antibacterial, anti-HIV, antidiabetic, antimalarial [4, 5, 6, 7, 8]. Furthermore, they are considered as significant fragments in many optoelectronic materials, such as laser dyes, fluorescent whiteners, organic light-emitting diodes (OLEDs), polymers, optical recording, organic solar cells, organic semiconductors, fluorescent probes, fluorescent activity, and sensitizers for dye-sensitized solar cells [9, 10, 11, 12].
Owing to these above-mentioned properties and broad chemical landscape, the construction and functionalization of molecules featuring heterocyclic framework as the key ingredients have attracted much more attention in synthetic organic chemistry [13, 14, 15, 16, 17]. However, the utilization of volatile organic solvents in a chemical process often results in the formation of chemical waste on both laboratory and industrial scales. This chemical waste was supposed to be one of the main sources of environmental pollution. Therefore, the design and development of a synthetic chemical route that leads to the expedient and rapid synthesis of diverse and highly functionalized heterocyclic scaffolds by avoiding or reducing the utilization of volatile organic solvents, toxic reagents, and hazardous chemicals to make our environment green and sustainable is highly desired and has emerged as a key challenge of modern synthetic organic chemistry. Furthermore, exploitation of energy in a chemical process either for heating or for cooling leads to an undesirable effect on the living environment.
To address many of these problems, mechanochemical methods, including ball-milling and grinding
But, again the occurrence of transition-metal-catalyst(s) in chemical processes even at the lowest level communicates the unfavorable effects on the atom economy and sustainability of the transformation. Notwithstanding, transition metal catalyst(s) has been successfully employed in the synthesis of valuable structural building blocks [24, 25, 26]; their occurrences in the chemical process caused serious effects because of their highly toxic nature, and the requirements of high cost for the preparation of catalytic system. Apart from these, the removal of transition-metal-catalyst(s) from the chemical transformation which is predominately needed in the pharmaceutical industry is not so easy and as a consequence, there will be high chances for contamination of the final compounds. Interestingly, the development of a synthetic chemical route for the construction of structural scaffolds with high atom- and step-economy which utilized alternative materials that are not only environmentally benign but also found to be in large scale in anywhere with minimum cost by reducing or circumventing the exploitation of transition metal catalyst(s), additives, supportive ligands, and toxic reagents to make a pollution-free environment are highly desired. For this purpose, the application of small organic molecules described as organocatalysts, in organic transformations have provided a new alternative route for the efficient synthesis of complex molecular structure in terms of synthetic efficiency and from the green chemistry viewpoint. The unique ability to accomplish chemical transformation through different activation modes, avoidance of expensive catalysts and metal catalyst(s), high stability, ready availability and easy recoverability, lower activation energy, high efficiency, as well as with an immediate reduction in the toxicity and reaction costs makes organocatalysis a highly advantageous and considerable approach in synthetic organic chemistry [13, 27, 28, 29, 30]. These advantages of organocatalysis can contribute to many of the requirements of green and sustainable chemistry.
Considering the versatile applicability of mechanochemical activation in organic synthesis and the significant contribution of organocatalysis in organic transformation, here we provide a critical overview on the organocatalytic expedient synthesis of different types of highly functionalized five- and six-membered heterocycles as well as complex-fused heterocycles and spiro-heterocycles by using mechanochemical techniques, including ball-milling and grinding with mortar and pestle. The mechanochemical activation in organic reactions is well-reviewed by many researchers [19, 20, 21, 22, 23, 31, 32, 33, 34, 35] and we hope, the present chapter would be helpful for researchers working in these fields.
2. Mechanochemical organocatalytic reactions for the synthesis of five-membered heterocycles
2.1 Synthesis of five-membered heterocycles containing one-heteroatom
2.1.1 Synthesis of pyrroles
The five-membered nitrogen-containing heterocycle, pyrroles and its derivatives are well-established building blocks of many naturally occurring and synthetic drug molecules [13]. The most commonly applied method for the synthesis of pyrroles realizes the Paal-Knorr method that involves the reaction of 1,4-dicarbonyl compounds and primary amines or ammonia.
In 2016, Akelis et al. [36] developed a simple, facile, and highly efficient mechanochemical method for the synthesis of a variety of substituted pyrroles
Another ball-milling approach for the synthesis of 3,4-disubstituted pyrroles has been accomplished by Bolm et al. [37] in 2021 (Figure 2). Under the influences of organic base DBU (1,8-Diazabicyclo[5.4.0]undec-7-ene), the desired products
2.1.2 Synthesis of furans
A simple but highly attractive one-pot procedure for the synthesis of
2.1.3 Synthesis of thiophenes
The Gewald method which involves the reaction of ketones, α-methylene carbonyl compounds, activated nitriles, and elemental sulfur is a well-established approach for the synthesis of 2-amino thiophenes. In this regard, Mack et al. [39] reported a Gewald reaction of acetophenone
2.2 Synthesis of five-membered heterocycles containing two-heteroatoms
2.2.1 Synthesis of pyrazoles
As nitrogen-containing heterocycle, pyrazole and their derivatives have a significant role in the field of medicinal chemistry and material sciences. As a consequence, substantial efforts have been dedicated to their synthesis [16]. In line with this, a highly efficient one-pot mechanochemical method for the synthesis of a series of sulfur-containing pyrazole derivatives
2.2.2 Synthesis of thiazoles
Edrees, Gomha et al. [41] demonstrated the successful application of mechanochemical techniques in the synthesis of a library of highly functionalized thiazole derivatives bearing pyrazole core in their structure (Figure 6
A very simple and straightforward grinding-assisted method to access benzo-fused thiazole derivatives under organocatalytic conditions was disclosed by Agarwal and Gandhi (Figure 7) [42]. In this context, they manually grind the readily available 2-aminobenzenethiol
2.2.3 Synthesis of imidazoles
Rajitha et al. [43] disclosed the utilization of grinding techniques for the condensation reaction of benzo[
2.3 Synthesis of five-membered heterocycles containing three-heteroatoms
2.3.1 Synthesis of oxadiazoles
Kategaonkar [44] developed an environmentally benign procedure for the construction of oxadiazole derivatives
2.3.2 Synthesis of thiadiazoles
Thiadiazoles are well-established five-membered heterocyclic compounds with three heteroatoms including two nitrogen atoms and one sulfur in their structure. They are known to be an important skeleton in medicinal and synthetic chemistry due to their wide prolific pharmacological profile. Considering their importance, Aziem et al. [45] introduced the grinding process as an eco-friendly and environmentally friendly chemical technology for the organocatalytic synthesis of various 1,3,4-thiadiazole derivatives
3. Mechanochemical organocatalytic reactions for the synthesis of six-membered heterocycles
3.1 Synthesis of six-membered heterocycles containing one-heteroatom
3.1.1 Synthesis of pyridines
Synthesis of a vast array of 1,4-dihydropyridine derivatives under mechanochemical activation has been achieved by Sarada et al. [46]. With the help of a mortar and pestle, grinding of readily available aldehydes
3.1.2 Synthesis of quinolines
A highly efficient and environmentally benign approach for the synthesis of polysubstituted quinolines
3.1.3 Synthesis of pyrans
The synthesis of 4
3.2 Synthesis of six-membered heterocycles containing two-heteroatoms
3.2.1 Synthesis of quinoxalines
Cellulose sulfuric acid was applied as an efficient metal-free organocatalytic system for the solid-state construction of highly functionalized quinoxaline derivatives by Rajitha et al. (Figure 14) [52]. By using a mortar and pestle, grinding of substituted 3-bromoacetyl coumarins
3.2.2 Synthesis of pyrimidines
Barman et al. [53] disclosed a metal-free highly convenient one-pot approach under mechanochemistry for the synthesis of 3,4-dihydropyrimidines. With the help of a mortar and pestle, the author’s grind substituted 1,3-diketones
3.2.3 Synthesis of quinazolinones
Quinazolinones and their derivatives are well-established heterocycles commonly encountered in many natural products and synthetic drug candidates. To realize their importance, a rapid mechanochemical assisted one-pot methodology for the synthesis of diverse quinazolinone derivatives has been developed by Shingare et al. (Figure 16) [54]. By introducing 10 mol% of vitamin B1, also known as thiamine hydrochloride as the organocatalyst, the solid-state treatment of anthranilic acid
Another achievement for the synthesis of different types of quinazolinones
4. Mechanochemical organocatalytic reactions for the synthesis of complex-fused poly-heterocycles
4.1 Synthesis of indazolo[2,1-b]phthalazine
An efficient eco- and environmentally friendly approach for the synthesis of complex-fused heterocycle, namely indazolo[2,1-
4.2 Synthesis of naphtho[2,3-b]thiophenes
A domino one-pot mechanochemical route toward the synthesis of naphtho-fused thiophene heterocycle was developed by the research group of Singh (Figure 19) [57]. By utilizing DMAP (4-Dimethylaminopyridine) as the metal-free catalyst, the oxidative [3 + 2] heteroannulation of 1,4-naphthoquinone
4.3 Synthesis of pyrano[4,3-b]pyrans
Khaligh et al. [58] demonstrated the successful application of ball-milling techniques in the multicomponent reaction of substituted aldehydes
4.4 Synthesis of pyrano[2,3-c]pyrazoles
A grinding assisted one-pot multicomponent approach for the rapid construction of pyrano[2,3-
4.5 Synthesis of triazolo[1,5-a]pyrimidine
Khaligh and Mihankhah [60] reported the exploitation of ball-milling techniques as a powerful alternative energy source in the three-component reaction of amino-substituted triazoles
5. Mechanochemical organocatalytic reactions for the synthesis of complex spiro-heterocycles
In the last few decades, the field of synthetic organic chemistry has witnessed outstanding developments in the synthesis of spiro-heterocycles especially spiro-oxindoles due to their outstanding reactivity and prolific pharmacological activity as well as their utilization as important building blocks for the synthesis of natural products types molecules as well as medicinally privileged heterocycles [61, 62].
Considering their importance in accordance with the significant application of mechanochemistry in synthetic organic chemistry, the research group of Bazgir [63] synthesized a series of spiro[diindenopyridine-indoline]triones
6. Conclusion
The frequent occurrence of heterocyclic compounds in natural, pharmaceutical, and synthetic optoelectronic materials, demands efficient methodology for their construction and selective functionalization by using them as key building blocks. But, the involvement of toxic solvents which are associated with chemical pollution often results in environmental safety concerns. Therefore, developing an alternative method to carry out organic synthesis by avoiding or minimizing the utilization of volatile organic solvents and toxic reagents by introducing environmentally benign conditions with the main focus to reduce the cost-effectiveness of the chemical transformation is highly desired. From the above observation, it is clear to conclude that the utilization of mechanochemical techniques allows all the reactions to be carried out in absence of volatile organic solvents, hazardous reagents and make them environmentally as well as eco-friendly benign. The mechanochemical techniques are found to be very efficient as compared to traditional stirring conditions from the perspective of synthetic as well as green chemistry points of view. The attractive benefits associated with mechanochemistry as a powerful alternative green energy source lead to a new frontier in the synthesis of diverse heterocyclic compounds as well as asymmetric synthesis and hope to consider as a method of choice both at the laboratory as well as in industrial level in near future.
Besides these, the development of organocatalytic reactions under mechanochemistry is set to lead the field of synthetic organic chemistry to a new height. The ability to accomplish reaction under the metal-free organocatalytic condition in the absence of solvent
On the other hand, some serious attention needs to be paid to broadening the substrate scopes, reducing the amount of catalyst, and developing a scalable protocol based on the industrial level.
Acknowledgments
The author thanks the Central University of Gujarat, Gandhinagar, India, and Prof. Rama Shanker Dubey, Vice-Chancellor, the Central University of Gujarat for the encouragement and continuous support. BB thanks UGC-India for the Non-NET fellowship.
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