| Peer-Reviewed

Deep Eutectic Solvent a Highly Efficient Medium for the Synthesis of Imidazo [1, 2-a] Pyridines Having Green Chemistry Approach

Received: 30 August 2022     Accepted: 27 September 2022     Published: 28 October 2022
Views:       Downloads:
Abstract

The imidazo [1, 2-a] pyridine is valuable structural unit in the area of natural products and pharmaceuticals. Extremely effective one pot method developed for the production of imidazo [1, 2-a] pyridines. The reaction of N-bromosuccinimide, acetophenones and 2-aminopyridines in deep eutectic solvent and reaction completed within a minute. The most remarkable features of such reaction is lowest minimum time, high atom, mild reaction condition and step economy. Methods The mixture of substituted acetophenones, N-bromosuccinimide in deep eutectic solvent as a green medium and 2-aminopyridines. The optimization of the reaction conditions with regard to their chemo selectivity of deep eutectic solvent. An imidazopyridine is a nitrogen containing heterocycle which plays crucial role in medicinal and pharmacological chemistry. Results To synthesize the imidazo [1, 2-a] pyridines, In the deep eutectic solvents add N-bromosuccinimide, acetophenones at room temperature immediately reaction completed within a minute, TLC Shows single spot which indicate that formation of α- bromoketones. On formation of α- bromoketones; 2-aminopyridine was added in the reaction mass after completion of reaction, the reaction mixture was poured in ice-cold water; the solid product obtained was filtered. Conclusion The main remarkable characteristics of this protocol such as no need to isolate lachrymatric α-bromoketones, clean reaction profile, mild reaction condition, require minimum reaction time, inexpensive and green aspects such as avoid hazardous solvents, poisonous catalyst, higher yield and ease of work-up.

Published in American Journal of Heterocyclic Chemistry (Volume 8, Issue 1)
DOI 10.11648/j.ajhc.20220801.12
Page(s) 7-11
Creative Commons

This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited.

Copyright

Copyright © The Author(s), 2022. Published by Science Publishing Group

Keywords

Deep Eutectic Solvent, Imidazol-Pyridine, Acetophenones, 2-Aminopyridines

References
[1] Almirante, L., Polo, L., Mugnaini, A., Provinciali, E., Rugarli, P., Biancotti, A., Gamba, A. and Murmann, W. Derivatives of imidazole. I. Journal of medicinal chemistry, 1965, 8 (3), pp. 305-312.
[2] Hemasrilatha, S., Sruthi, K., Manjula, A., Babu, V. H. and Rao, B. V. Synthesis and anti-inflammatory activity of imidazo [1, 2-a] pyridinyl/pyrazinyl benzamides and acetamides. Indian Journal of Chemistry, Vol. 51B, July 2012, pp 981-987.
[3] Dymińska, L., 2015. Imidazopyridines as a source of biological activity and their pharmacological potentials—infrared and Raman spectroscopic evidence of their content in pharmaceuticals and plant materials. Bioorganic & Medicinal Chemistry, 23 (18), pp. 6087-6099.
[4] Gaba, M. and Mohan, C., 2016. Development of drugs based on imidazole and benzimidazole bioactive heterocycles: recent advances and future directions. Medicinal Chemistry Research, 25 (2), pp. 173-210. Zhao, C., Li, F., Yang, S., Liu, L., Huang, Z. and Chai, H. Heterocyclic Compounds, 201`8, 54 (5), pp. 568-571.
[5] Ebenezer, O., Jordaan, M. A., Carena, G., Bono, T., Shapi, M. and Tuszynski, J. A., 2022. An Overview of the Biological Evaluation of Selected Nitrogen-Containing Heterocycle Medicinal Chemistry Compounds. International Journal of Molecular Sciences, 23 (15), p. 8117.
[6] Enguehard-Gueiffier, C. and Gueiffier, A., 2007. Recent Progress in the Pharmacology of Imidazo [1, 2-a] pyridines. Mini Reviews in Medicinal Chemistry, 7 (9), pp. 888-899.
[7] Lin, X., Kang, D., Li, X., Zhan, P., Liu, X. and Zhang, Q., 2014. Discovery and characterization of novel imidazopyridine derivative CHEQ-2 as a potent CDC25 inhibitor and promising anticancer drug candidate. European journal of medicinal chemistry, 82, pp. 293-307.
[8] LS Kishbaugh, T. Pyridines and Imidazopyridines with medicinal significance. Current topics in medicinal chemistry, 2016, 16 (28), pp. 3274-3302.
[9] Bagdi, A. K., Santra, S., Monir, K. and Hajra, A., 2015. Synthesis of imidazo [1, 2-a] pyridines: a decade update. Chemical Communications, 51 (9), pp. 1555-1575.
[10] Gudmundsson, K. S., Williams, J. D., Drach, J. C. and Townsend, L. B., 2003. Synthesis and antiviral activity of novel erythrofuranosyl imidazo [1, 2-a] pyridine C-nucleosides constructed via palladium coupling of iodoimidazo [1, 2-a] pyridines and dihydrofuran. Journal of medicinal chemistry, 46 (8), pp. 1449-1455.
[11] Sivappa, R., Sammeta, V. R., Huang, Y., Golen, J. A. and Savinov, S. N., 2019. Facile synthesis of 3-substituted imidazo [1, 2-a] pyridines through formimidamide chemistry. RSC advances, 9 (51), pp. 29659-29664.
[12] López-Martínez, M., Salgado-Zamora, H., Campos-Aldrete, M., Trujillo-Ferrara, J. G., Correa-Basurto, J. and Mexica-Ochoa, C., 2012. Effect of the lipophilic parameter (log P) on the anti-parasitic activity of imidazo [1, 2-a] pyridine derivatives. Medicinal Chemistry Research, 21 (4), pp. 415-420.
[13] Koubachi, J., El Kazzouli, S., Bousmina, M. and Guillaumet, G., 2014. Functionalization of imidazo [1, 2-a] pyridines by means of metal-catalyzed cross-coupling reactions. European Journal of Organic Chemistry, 2014 (24), pp. 5119-5138.
[14] Lacerda, R. B., de Lima, C. K., da Silva, L. L., Romeiro, N. C., Miranda, A. L. P., Barreiro, E. J. and Fraga, C. A., 2009. Discovery of novel analgesic and anti-inflammatory 3-arylamine-imidazo [1, 2-a] pyridine symbiotic prototypes. Bioorganic & medicinal chemistry, 17 (1), pp. 74-84.
[15] Deep, A., Kaur Bhatia, R., Kaur, R., Kumar, S., Kumar Jain, U., Singh, H., Batra, S., Kaushik, D. and Kishore Deb, P., 2017. Imidazo [1, 2-a] pyridine scaffold as prospective therapeutic agents. Current topics in medicinal chemistry, 17 (2), pp. 238-250.
[16] Dam, J., Ismail, Z., Kurebwa, T., Gangat, N., Harmse, L., Marques, H. M., Lemmerer, A., Bode, M. L. and de Koning, C. B., 2017. Synthesis of copper and zinc 2-(pyridin-2-yl) imidazo [1, 2-a] pyridine complexes and their potential anticancer activity. European journal of medicinal chemistry, 126, pp. 353-368.
[17] Scribner, A., Dennis, R., Lee, S., Ouvry, G., Perrey, D., Fisher, M., Wyvratt, M., Leavitt, P., Liberator, P., Gurnett, A. and Brown, C., 2008. Synthesis and biological activity of imidazopyridine anticoccidial agents: part II. European journal of medicinal chemistry, 43 (6), pp. 1123-1151. Bhale, P. S. 2013, 2, 1-6, 2013.
[18] Bhale, P. S., Dongare, S. B. and Chanshetti, U. B., 2013. Synthesis and antimicrobial screening of chalcones containing imidazo [1, 2-a] pyridine nucleus. Research Journal of Chemical Sciences, 2231, p. 606X. Paengphua, P., & Chancharunee, S. 2018, 149 (10), 1835-1840.
[19] Warshakoon, N. C., Wu, S., Boyer, A., Kawamoto, R., Sheville, J., Renock, S., Xu, K., Pokross, M., Evdokimov, A. G., Walter, R. and Mekel, M., 2006. A novel series of imidazo [1, 2-a] pyridine derivatives as HIF-1α prolyl hydroxylase inhibitors. Bioorganic & medicinal chemistry letters, 16 (21), pp. 5598-5601.
[20] Starrett Jr, J. E., Montzka, T. A., Crosswell, A. R. and Cavanagh, R. L., 1989. Synthesis and biological activity of 3-substituted imidazo [1, 2-a] pyridines as antiulcer agents. Journal of medicinal chemistry, 32 (9), pp. 2204-2210.
[21] Santra, S., Bagdi, A. K., Majee, A. and Hajra, A., 2013. Iron (III)-Catalyzed Cascade Reaction between Nitroolefins and 2-Aminopyridines: Synthesis of Imidazo [1, 2-a] Pyridines and Easy Access towards Zolimidine. Advanced Synthesis & Catalysis, 355 (6), pp. 1065-1070.
[22] Said, M. S., Mishra, A., Pandole, S., Nayak, R. A., Kumar, P. and Gajbhiye, J. M., 2019. Regioselective One-Pot Synthesis of 3-Fluoro-Imidazo [1, 2-a] pyridines from Styrene. Asian Journal of Organic Chemistry, 8 (11), pp. 2143-2148.
[23] Chitti, S., Singireddi, S., Reddy, P. S. K., Trivedi, P., Bobde, Y., Kumar, C., Rangan, K., Ghosh, B. and Sekhar, K. V. G. C., 2019. Design, synthesis and biological evaluation of 2-(3, 4-dimethoxyphenyl)-6 (1, 2, 3, 6-tetrahydropyridin-4-yl) imidazo [1, 2-a] pyridine analogues as antiproliferative agents. Bioorganic & Medicinal Chemistry Letters, 29 (18), pp. 2551-2558.
[24] Ducray, R., Boutron, P., Didelot, M., Germain, H., Lach, F., Lamorlette, M., Legriffon, A., Maudet, M., Ménard, M., Pasquet, G. and Renaud, F., 2010. A versatile route to 3-(pyrimidin-4-yl)-imidazo [1, 2-a] pyridines and 3-(pyrimidin-4-yl)-pyrazolo [1, 5-a] pyridines. Tetrahedron letters, 51 (36), pp. 4755-4758.
[25] Kurva, M., Pharande, S. G., Quezada-Soto, A. and Gámez-Montaño, R., 2018. Ultrasound assisted green synthesis of bound type bis-heterocyclic carbazolyl imidazo [1, 2-a] pyridines via Groebke-Blackburn-Bienayme reaction. Tetrahedron Letters, 59 (16), pp. 1596-1599.
[26] Balalaie, S., Derakhshan-Panah, F., Zolfigol, M. A. and Rominger, F., 2018. A Convenient Method for the Synthesis of Imidazo [1, 2-a] pyridines with a New Approach. Synlett, 29 (01), pp. 89-93.
[27] Tiwari, G., Kumar, M., Chauhan, A. N. S. and Erande, R. D., 2022. Recent advances in cascade reactions and their mechanistic insights: a concise strategy to synthesize complex natural products and organic scaffolds. Organic & Biomolecular Chemistry.
[28] Neto, J. S., Balaguez, R. A., Franco, M. S., de Sa Machado, V. C., Saba, S., Rafique, J., Galetto, F. Z. and Braga, A. L., 2020. Trihaloisocyanuric acids in ethanol: an eco-friendly system for the regioselective halogenation of imidazo-heteroarenes. Green Chemistry, 22 (11), pp. 3410-3415.
[29] Xia, B., Yan, D., Bai, Y., Xie, J., Cao, Y., Liao, D. and Lin, L., 2015. Determination of phenolic acids in Prunella vulgaris L.: a safe and green extraction method using alcohol-based deep eutectic solvents. Analytical Methods, 7 (21), pp. 9354-9364.
[30] Pericherla, K., Kaswan, P., Pandey, K. and Kumar, A., 2015. Recent developments in the synthesis of imidazo [1, 2-a] pyridines. Synthesis, 47 (07), pp. 887-912.
[31] Kurteva, V. B., Lubenov, L. A. and Antonova, D. V., 2014. On the mechanism of the direct acid catalyzed formation of 2, 3-disubstituted imidazo [1, 2-a] pyridines from 2-aminopyridines and acetophenones. Concurrence between ketimine and Ortoleva–King type reaction intermediated transformations. RSC advances, 4 (1), pp. 175-184.
[32] Krasovsky, A. L., Nenajdenko, V. G. and Balenkova, E. S., 2002. A facile access to 2-CF3-imidazo [1, 2-a] pyridines. Synthesis, 2002 (10), pp. 1379-1384.
[33] Yadav, J. S., Reddy, B. S., Rao, Y. G., Srinivas, M. and Narsaiah, A. V., 2007. Cu (OTf) 2-catalyzed synthesis of imidazo [1, 2-a] pyridines from α-diazoketones and 2-aminopyridines. Tetrahedron Letters, 48 (43), pp. 7717-7720.
[34] Shaikh, M., Shaikh, M., Wagare, D., Ahmed Sheikh, A. and Sultan Kasim, S., 2022. Deep Eutectic Solvent (DES) Mediated Multicomponent Synthesis of 4-thiazolidinone-5-carboxylic Acid: A Green Chemistry Approach. Current Catalysis, 11 (1), pp. 65-70.
[35] Wagare, D. S., Shaikh, M. H., Farooqui, M. and Durrani, A. N., Ultrasound promoted one-pot synthesis of imidazo [1, 2-a] pyridines in water.
[36] Shaikh, M., Wagare, D., Farooqui, M. and Durrani, A., 2020. Microwave assisted synthesis of novel schiff bases of pyrazolyl carbaldehyde and triazole in PEG-400. Polycyclic Aromatic Compounds, 40 (5), pp. 1315-1320.
[37] Harris, A. R., Nason, D. M., Collantes, E. M., Xu, W., Chi, Y., Wang, Z., Zhang, B., Zhang, Q., Gray, D. L. and Davoren, J. E., 2011. Synthesis of 5-bromo-6-methyl imidazopyrazine, 5-bromo and 5-chloro-6-methyl imidazopyridine using electron density surface maps to guide synthetic strategy. Tetrahedron, 67 (47), pp. 9063-9066.
[38] Kondo, T., Kotachi, S., Ogino, S. I. and Watanabe, Y., 1993. Ruthenium Complex-catalyzed Novel and Facile Synthesis of Imidazo [1, 2-a] pyridines from 2-Aminopyridines and vicinal-Diols. Chemistry letters, 22 (8), pp. 1317-1320.
[39] Zhu, D. J., Chen, J. X., Liu, M. C., Ding, J. C. and Wu, H. Y., 2009. Catalyst: and solvent-free synthesis of imidazo [1, 2-a] pyridines. Journal of the Brazilian Chemical Society, 20, pp. 482-487.
[40] Gudmundsson, K. S. and Johns, B. A., 2003. Synthesis of novel imidazo [1, 2-a] pyridines with potent activity against herpesviruses. Organic Letters, 5 (8), pp. 1369-1372.
[41] Vekariya, R. H., Patel, K. D. and Patel, H. D., 2016. Fruit juice of Citrus limon as a biodegradable and reusable catalyst for facile, eco-friendly and green synthesis of 3, 4-disubstituted isoxazol-5 (4H)-ones and dihydropyrano [2, 3-c]-pyrazole derivatives. Research on Chemical Intermediates, 42 (10), pp. 7559-7579.
[42] Roslan, I. I., Ng, K. H., Wu, J. E., Chuah, G. K. and Jaenicke, S., 2016. Synthesis of Disubstituted 3-Phenylimidazo [1, 2-a] pyridines via a 2-Aminopyridine/CBrCl3 α-Bromination Shuttle. The Journal of organic chemistry, 81 (19), pp. 9167-9174.
Cite This Article
  • APA Style

    Majid Shaikh, Sayyad Sultan Kasim. (2022). Deep Eutectic Solvent a Highly Efficient Medium for the Synthesis of Imidazo [1, 2-a] Pyridines Having Green Chemistry Approach. American Journal of Heterocyclic Chemistry, 8(1), 7-11. https://doi.org/10.11648/j.ajhc.20220801.12

    Copy | Download

    ACS Style

    Majid Shaikh; Sayyad Sultan Kasim. Deep Eutectic Solvent a Highly Efficient Medium for the Synthesis of Imidazo [1, 2-a] Pyridines Having Green Chemistry Approach. Am. J. Heterocycl. Chem. 2022, 8(1), 7-11. doi: 10.11648/j.ajhc.20220801.12

    Copy | Download

    AMA Style

    Majid Shaikh, Sayyad Sultan Kasim. Deep Eutectic Solvent a Highly Efficient Medium for the Synthesis of Imidazo [1, 2-a] Pyridines Having Green Chemistry Approach. Am J Heterocycl Chem. 2022;8(1):7-11. doi: 10.11648/j.ajhc.20220801.12

    Copy | Download

  • @article{10.11648/j.ajhc.20220801.12,
      author = {Majid Shaikh and Sayyad Sultan Kasim},
      title = {Deep Eutectic Solvent a Highly Efficient Medium for the Synthesis of Imidazo [1, 2-a] Pyridines Having Green Chemistry Approach},
      journal = {American Journal of Heterocyclic Chemistry},
      volume = {8},
      number = {1},
      pages = {7-11},
      doi = {10.11648/j.ajhc.20220801.12},
      url = {https://doi.org/10.11648/j.ajhc.20220801.12},
      eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ajhc.20220801.12},
      abstract = {The imidazo [1, 2-a] pyridine is valuable structural unit in the area of natural products and pharmaceuticals. Extremely effective one pot method developed for the production of imidazo [1, 2-a] pyridines. The reaction of N-bromosuccinimide, acetophenones and 2-aminopyridines in deep eutectic solvent and reaction completed within a minute. The most remarkable features of such reaction is lowest minimum time, high atom, mild reaction condition and step economy. Methods The mixture of substituted acetophenones, N-bromosuccinimide in deep eutectic solvent as a green medium and 2-aminopyridines. The optimization of the reaction conditions with regard to their chemo selectivity of deep eutectic solvent. An imidazopyridine is a nitrogen containing heterocycle which plays crucial role in medicinal and pharmacological chemistry. Results To synthesize the imidazo [1, 2-a] pyridines, In the deep eutectic solvents add N-bromosuccinimide, acetophenones at room temperature immediately reaction completed within a minute, TLC Shows single spot which indicate that formation of α- bromoketones. On formation of α- bromoketones; 2-aminopyridine was added in the reaction mass after completion of reaction, the reaction mixture was poured in ice-cold water; the solid product obtained was filtered. Conclusion The main remarkable characteristics of this protocol such as no need to isolate lachrymatric α-bromoketones, clean reaction profile, mild reaction condition, require minimum reaction time, inexpensive and green aspects such as avoid hazardous solvents, poisonous catalyst, higher yield and ease of work-up.},
     year = {2022}
    }
    

    Copy | Download

  • TY  - JOUR
    T1  - Deep Eutectic Solvent a Highly Efficient Medium for the Synthesis of Imidazo [1, 2-a] Pyridines Having Green Chemistry Approach
    AU  - Majid Shaikh
    AU  - Sayyad Sultan Kasim
    Y1  - 2022/10/28
    PY  - 2022
    N1  - https://doi.org/10.11648/j.ajhc.20220801.12
    DO  - 10.11648/j.ajhc.20220801.12
    T2  - American Journal of Heterocyclic Chemistry
    JF  - American Journal of Heterocyclic Chemistry
    JO  - American Journal of Heterocyclic Chemistry
    SP  - 7
    EP  - 11
    PB  - Science Publishing Group
    SN  - 2575-5722
    UR  - https://doi.org/10.11648/j.ajhc.20220801.12
    AB  - The imidazo [1, 2-a] pyridine is valuable structural unit in the area of natural products and pharmaceuticals. Extremely effective one pot method developed for the production of imidazo [1, 2-a] pyridines. The reaction of N-bromosuccinimide, acetophenones and 2-aminopyridines in deep eutectic solvent and reaction completed within a minute. The most remarkable features of such reaction is lowest minimum time, high atom, mild reaction condition and step economy. Methods The mixture of substituted acetophenones, N-bromosuccinimide in deep eutectic solvent as a green medium and 2-aminopyridines. The optimization of the reaction conditions with regard to their chemo selectivity of deep eutectic solvent. An imidazopyridine is a nitrogen containing heterocycle which plays crucial role in medicinal and pharmacological chemistry. Results To synthesize the imidazo [1, 2-a] pyridines, In the deep eutectic solvents add N-bromosuccinimide, acetophenones at room temperature immediately reaction completed within a minute, TLC Shows single spot which indicate that formation of α- bromoketones. On formation of α- bromoketones; 2-aminopyridine was added in the reaction mass after completion of reaction, the reaction mixture was poured in ice-cold water; the solid product obtained was filtered. Conclusion The main remarkable characteristics of this protocol such as no need to isolate lachrymatric α-bromoketones, clean reaction profile, mild reaction condition, require minimum reaction time, inexpensive and green aspects such as avoid hazardous solvents, poisonous catalyst, higher yield and ease of work-up.
    VL  - 8
    IS  - 1
    ER  - 

    Copy | Download

Author Information
  • Department of Chemistry, Maulana Azad College, Aurangabad, India

  • Department of Chemistry, Maulana Azad College, Aurangabad, India

  • Sections