Issue

Vol. 35 No. 1 (2023): Vol 35 Issue 1

Copyright (c) 2023 AJC

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

Acetic Acid-Water Mediated Efficient One-Pot Synthesis of Functionalized Isoxazolyl Amino Chromeno[4,3-b]pyridine Derivatives

https://doi.org/10.14233/ajchem.2023.26926
Ravinder Reddy Danda
Department of Chemistry, University College of Science, Osmania University, Hyderabad-500007, India
P. Muralidhar Reddy
Department of Chemistry, University College of Science, Osmania University, Hyderabad-500007, India
A. Krishnam Raju
Department of Chemistry, University College of Science, Osmania University, Hyderabad-500007, India
V. Naveen Reddy
Department of Chemistry, Nizam College, Osmania University, Hyderabad-500001, India
K. Santosh Kumar
Department of Chemistry, Geethanjali College of Engineering and Technology, Hyderabad-501301, India
B. Vijaya Kumar
Department of Chemistry, University College of Science, Osmania University, Hyderabad-500007, India

Corresponding Author(s) : B. Vijaya Kumar

vijayakumarou21@gmail.com

Asian Journal of Chemistry, Vol. 35 No. 1 (2023): Vol 35 Issue 1

Abstract

A simple, efficient, economical and environmentally benign method has been developed for one-pot three component synthesis of isoxazolyl amino chromeno[4,3-b]pyridine derivatives from 4-amino-3-methyl-5-styrylisoxazoles, malononitrile and (E)-3-benzylidenechroman-4-one by using acetic acid (AcOH) as a promoter and water as a green reaction medium under thermal condition. The interesting features of this method are environmental friendly, metal-free, less reaction time, wide substrate scope, operational simplicity, easy purification of products and good yields.

Keywords

One-pot reaction Green chemistry Water Acetic acid Isoxazolyl amino chromeno[4,3-b]pyridine
Reddy Danda, R., Muralidhar Reddy, P., Krishnam Raju, A., Naveen Reddy, V., Santosh Kumar, K., & Vijaya Kumar, B. (2022). Acetic Acid-Water Mediated Efficient One-Pot Synthesis of Functionalized Isoxazolyl Amino Chromeno[4,3-b]pyridine Derivatives. Asian Journal of Chemistry, 35(1), 135–142. https://doi.org/10.14233/ajchem.2023.26926
Download Citation
Endnote/Zotero/Mendeley (RIS)
BibTeX
References
  1. N. Winterton, Clean Technol. Environ. Policy, 23, 2499 (2021); https://doi.org/10.1007/s10098-021-02188-8
  2. K. Aplander, O. Hidestal, K. Katebzadeh and U.M. Lindstrom, Green Chem., 8, 22 (2006); https://doi.org/10.1039/B513656C
  3. X.Y. Liu and C.M. Che, Angew. Chem. Int. Ed. Engl., 47, 3805 (2008); https://doi.org/10.1002/anie.200800160
  4. C.I. Herrerias, X. Yao, Z. Li and C.-J. Li, Chem. Rev., 107, 2546 (2007); https://doi.org/10.1021/cr050980b
  5. A. Chanda and V.V. Fokin, Chem. Rev., 109, 725 (2009); https://doi.org/10.1021/cr800448q
  6. M. Li, Z. Zuo, L. Wen and S. Wang, J. Comb. Chem., 10, 436 (2008); https://doi.org/10.1021/cc700194b
  7. J. Zhu and H. Bienayme, Multicomponent Reactions, Weinheim: Wiley, p. 121 (2005).
  8. N. Kerru, L. Gummidi, S. Maddila, K.K. Gangu and S.B. Jonnalagadda, Molecules, 25, 1909 (2020); https://doi.org/10.3390/molecules25081909
  9. M.M. Heravi and V. Zadsirjan, RSC Adv., 10, 44247 (2020); https://doi.org/10.1039/D0RA09198G
  10. A.S. Santos, D. Raydan, J.C. Cunha, N. Viduedo, A.M.S. Silva and M.M.B. Marques, Catalysts, 11, 1108 (2021); https://doi.org/10.3390/catal11091108
  11. C.P. Ridley, M.V.R. Reddy, G. Rocha, F.D. Bushman and D.J. Faulknera, Bioorg. Med. Chem., 10, 3285 (2002); https://doi.org/10.1016/S0968-0896(02)00237-7
  12. H. Fan, J. Peng, M.T. Hamann and J.F. Hu, Chem. Rev., 108, 264 (2008); https://doi.org/10.1021/cr078199m
  13. U. Thapa, P. Thapa, R. Karki, M. Yun, J.H. Choi, Y. Jahng, E. Lee, K.H. Jeon, Y. Na, E. Ha, W. Cho, Y. Kwon and E. Lee, Eur. J. Med. Chem., 46, 3201 (2011); https://doi.org/10.1016/j.ejmech.2011.04.029
  14. H.-B. Kwon, C. Park, K.-H. Jeon, E. Lee, S.-E. Park, K.-Y. Jun, T.M. Kadayat, P. Thapa, R. Karki, Y. Na, M.S. Park, S.B. Rho, E.-S. Lee and Y. Kwon, J. Med. Chem., 58, 1100 (2015); https://doi.org/10.1021/jm501023q
  15. A.A. Patel, H.B. Lad, K.R. Pandya, C.V. Patel and D.I. Brahmbhatt, Med. Chem. Res., 22, 4745 (2013); https://doi.org/10.1007/s00044-013-0489-4
  16. S.G. Rani, S.K. Mohan and C. Yu, Biochemistry, 49, 2585 (2010); https://doi.org/10.1021/bi9019077
  17. N. Agrawal and P. Mishra, Med. Chem. Res., 27, 1309 (2018); https://doi.org/10.1007/s00044-018-2152-6
  18. C.P. Pandhurnekar, H.C. Pandhurnekar, A.J. Mungole, S.S. Butoliya and B.G. Yadao, J. Heterocycl. Chem., (2022); https://doi.org/10.1002/jhet.4586
  19. G. Daidone, D. Raffa, B. Maggio, F. Plescia, V.M.C. Cutuli, N.G. Mangano and A. Caruso, Arch. Pharm. Med. Chem., 332, 50 (1999); https://doi.org/10.1002/(SICI)1521-4184(19993)332:2<50::AIDARDP50>3.0.CO;2-S
  20. J.J. Talley, D.L. Brown, J.S. Carter, M.J. Graneto, C.M. Koboldt, J.L. Masferrer, W.E. Perkins, R.S. Rogers, A.F. Shaffer, Y.Y. Zhang, B.S. Zweifel and K. Seibert, J. Med. Chem., 43, 775 (2000); https://doi.org/10.1021/jm990577v
  21. W.-T. Li, D.-R. Hwang, C.-P. Chen, C.-W. Shen, C.-L. Huang, T.-W. Chen, C.-H. Lin, Y.-L. Chang, Y.-Y. Chang, Y.-K. Lo, H.-Y. Tseng, C.- C. Lin, J.-S. Song, H.-C. Chen, S.-J. Chen, S.-H. Wu and C.-T. Chen, J. Med. Chem., 46, 1706 (2003); https://doi.org/10.1021/jm020471r
  22. S. Keskin and M. Balci, Org. Lett., 17, 964 (2015); https://doi.org/10.1021/acs.orglett.5b00067
  23. K. Aradi, P. Bombicz and Z.J. Novák, J. Org. Chem., 81, 920 (2016); https://doi.org/10.1021/acs.joc.5b02490
  24. S. Gupta and J.M. Khurana, Green Chem., 19, 4153 (2017); https://doi.org/10.1039/C7GC01463E
  25. F.-C. Yu, X.-R. Lin, Z.-C. Liu, J.-H. Zhang, F.-F. Liu, W. Wu, Y.-L. Ma, W.-W. Qu, S.-J. Yan and J. Lin, ACS Omega, 2, 873 (2017); https://doi.org/10.1021/acsomega.6b00545
  26. N. Poomathi, P.T. Perumal and S. Ramakrishna, Green Chem., 19, 2524 (2017); https://doi.org/10.1039/C6GC03440C
  27. L. Chen, R. Huang, X.-X. Du, S.-J. Yan and J. Lin, ACS Sustain. Chem. Eng., 5, 1899 (2017); https://doi.org/10.1021/acssuschemeng.6b02622
  28. J. Xiao, Y.Y. Chen, S. Zhu, L. Wang, L.B. Xu and H.T. Wei, Adv. Synth. Catal., 356, 1835 (2014); https://doi.org/10.1002/adsc.201301171
  29. M.N. Reddy and P.P. Kumar, Tetrahedron Lett., 58, 4790 (2017); https://doi.org/10.1016/j.tetlet.2017.11.027
  30. N.V. Rani and K. Ravindhranath, Synth. Commun., 51, 1171 (2021); https://doi.org/10.1080/00397911.2021.1871759
  31. D. Nagaraju, E. Rajanarendar, P.P. Kumar and M. Nagi Reddy, New J. Chem., 41, 4783 (2017); https://doi.org/10.1039/C7NJ01165B
  32. N.R. Modugu and P.K. Pittala, New J. Chem., 41, 14062 (2017); https://doi.org/10.1039/C7NJ03515B
  33. S.V. Rayudu, D. Karmakar and P. Kumar, Tetrahedron Lett., 60, 151025 (2019); https://doi.org/10.1016/j.tetlet.2019.151025
  34. E. Rajanarendar, M. Nagi Reddy, S. Rama Krishna, K. Rama Murthy, Y.N. Reddy and M.V. Rajam, Eur. J. Med. Chem., 55, 273 (2012); https://doi.org/10.1016/j.ejmech.2012.07.029
  35. E. Rajanarendar, M.N. Reddy, S.R. Krishna, K.G. Reddy, Y.N. Reddy and M.V. Rajam, Eur. J. Med. Chem., 50, 344 (2012); https://doi.org/10.1016/j.ejmech.2012.02.013
  36. E. Rajanarendar, M.N. Reddy, K.R. Murthy, P. Surendar, R.N. Reddy and Y.N. Reddy, Bioorg. Med. Chem. Lett., 22, 149 (2012); https://doi.org/10.1016/j.bmcl.2011.11.044
Read More
Author biographies is not available.
Download
PDF
Statistic
Read Counter : 2 Download : 0