Issue

Vol. 35 No. 2 (2023): Vol 35 Issue 2, 2023

Copyright (c) 2023 AJC

Creative Commons License

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

Synthesis of Novel Biaryl Fused Thiazolo[3,2-b][1,2,4]triazol-2-amines from Thiazole Amine Involving Suzuki Coupling Reaction under Microwave Irradiation

https://doi.org/10.14233/ajchem.2023.26998
Krishna Chaitanya Veeranki
Department of Chemistry, Jawaharlal Nehru Technological University Hyderabad, College of Engineering, Kukatpally, Hyderabad-500085, India ; Chemveda Life Sciences Pvt Ltd., IDA Uppal, Hyderabad-500039, India
Jalapathi Pochampally
Department of Chemistry, Osmania University, Hyderabad-500007, India
Ravi Chander Maroju
Department of Chemistry, Mahatma Gandhi Institute of Technology, Hyderabad-500075, India

Corresponding Author(s) : Jalapathi Pochampally

pochampalli.ou.chemi@gmail.com

Asian Journal of Chemistry, Vol. 35 No. 2 (2023): Vol 35 Issue 2, 2023

Abstract

Novel series of fused heterocycles in which amino triazole fused to biphenyl thiazole were synthesized in a multistep reaction starting from 2-aminothiazole. The amino compound with ethoxy carbonyl isothiocyanate afforded the ethyl carbamate thiomide derivative of thiazole, which further underwent intramolecular cyclization with hydroxyl amine hydrochloride in presence of DIPEA to furnish the fused thiazolotriazole amine. Haloaryl group in the fused heterocycle under Suzuki coupling condition afforded biphenyl derivatives of fused thiazolotriazole amines. All the synthesized compounds were confirmed based on their spectral data.

Keywords

Biaryl Suzuki coupling Microwave irradiation Fused thiazolo 1,2,4-triazole
Chaitanya Veeranki, K., Pochampally, J., & Maroju, R. C. (2023). Synthesis of Novel Biaryl Fused Thiazolo[3,2-b][1,2,4]triazol-2-amines from Thiazole Amine Involving Suzuki Coupling Reaction under Microwave Irradiation. Asian Journal of Chemistry, 35(2), 431–434. https://doi.org/10.14233/ajchem.2023.26998
Download Citation
Endnote/Zotero/Mendeley (RIS)
BibTeX
References
  1. A. Abdelli, S. Azzouni, R. Plais, A. Gaucher, M.L. Efrit and D. Prim, Tetrahedron Lett., 86, 153518 (2021); https://doi.org/10.1016/j.tetlet.2021.153518
  2. Z. Xu, S.-J. Zhao and Y. Liu, Eur. J. Med. Chem., 183, 111700 (2019); https://doi.org/10.1016/j.ejmech.2019.111700
  3. S. Cai, Q.-S. Li, R.T. Borchardt, K. Kuczera and R.L. Schowen, Bioorg. Med. Chem., 15, 7281 (2007); https://doi.org/10.1016/j.bmc.2007.08.029
  4. R. Paprocka, M. Wiese, A. Eljaszewicz, A. Helmin-Basa, A. Gzella, B. Modzelewska-Banachiewicz and J. Michalkiewicz, Bioorg. Med. Chem. Lett., 25, 2664 (2015); https://doi.org/10.1016/j.bmcl.2015.04.079
  5. M.A. Ghannoum and L.B. Rice, Clin. Microbiol. Rev., 12, 501 (1999); https://doi.org/10.1128/CMR.12.4.501
  6. A.U. Buzdar, J.F.R. Robertson, W. Eiermann and J.-M. Nabholtz, Cancer, 95, 2006 (2002); https://doi.org/10.1002/cncr.10908
  7. J. Geisler, H. Helle, D. Ekse, N.K. Duong, D.B. Evans, Y. Nordbø, T. Aas and P.E. Lønning, Clin. Cancer Res., 14, 6330 (2008); https://doi.org/10.1158/1078-0432.CCR-07-5221
  8. S.G. Küçükgüzel and P. Çikla-Süzgün, Eur. J. Med. Chem., 97, 830 (2015); https://doi.org/10.1016/j.ejmech.2014.11.033
  9. I. Küçükgüzel, S. Rollas and A. Çevikbas, Drug Metabol. Drug Interact., 12, 151 (1995); https://doi.org/10.1515/DMDI.1995.12.2.151
  10. T.N. Franklim, L. Freire-de-Lima, J. de Nazareth Sá Diniz, J. Previato, R. Castro, L. Mendonça-Previato and M. de Lima, Molecules, 18, 6366 (2013); https://doi.org/10.3390/molecules18066366
  11. G.S. Hassan, S.M. El-Messery, F.A. Al-Omary, S.T. Al-Rashood, M.I. Shabayek, Y.S. Abulfadl, E.-S.E. Habib, S.M. El-Hallouty, W. Fayad, K.M. Mohamed, B.S. El-Menshawi and H.I. El-Subbagh, Eur. J. Med. Chem., 66, 135 (2013); https://doi.org/10.1016/j.ejmech.2013.05.039
  12. A.T.A. Boraei, M.S. Gomaa, E.S.H. El Ashry and A. Duerkop, Eur. J. Med. Chem., 125, 360 (2017); https://doi.org/10.1016/j.ejmech.2016.09.046
  13. M.R. Aouad, M.M. Mayaba, A. Naqvi, S.K. Bardaweel, F.F. Al-blewi, M. Messali and N. Rezki, Chem. Cent. J., 11, 117 (2017); https://doi.org/10.1186/s13065-017-0347-4
  14. K.T. Potts, Chem. Rev., 61, 87 (1961); https://doi.org/10.1021/cr60210a001
  15. E.F.V. Scriven, M. Balasubramanian, J.G. Keay and N. Shobana, Heterocycles, 37, 1951 (1994); https://doi.org/10.3987/REV-93-SR11
  16. A.D. Curtis, Sci. Synth., 13, 603 (2004).
  17. J.W. Hull Jr., D.R. Romer, T.-J. Adaway and D.E. Podhorez, Org. Process Res. Dev., 13, 1125 (2009); https://doi.org/10.1021/op9001577
  18. J. Sun, A. Zhang, J. Zhang, X. Xie and W.-J. Liu, J. Agric. Food Chem., 60, 160 (2012); https://doi.org/10.1021/jf203742x
  19. I.A. Al-Masoudi, Y.A. Al-Soud, N.J. Al-Salihi and N.A. Al-Masoudi, Chem. Heterocycl. Compd., 42, 1377 (2006); https://doi.org/10.1007/s10593-006-0255-3
  20. E. Huntsman and J. Balsells, Eur. J. Org. Chem., 3761 (2005); https://doi.org/10.1002/ejoc.200500247
  21. N.-M. Parekh, K.-V. Juddhawala and B.-M. Rawal, Med. Chem. Res., 22, 2737 (2013); https://doi.org/10.1007/s00044-012-0273-x
  22. M.M. Matin, P. Matin, M.R. Rahman, T.B. Hadda, F.A. Almalki, S. Mahmud, M.M. Ghoneim, M. Alruwaily and S. Alshehri, Front. Mol. Biosci., 9, 864286 (2022); https://doi.org/10.3389/fmolb.2022.864286
  23. S.F. Barbuceanu, G.L. Almajan, C. Draghici, A.I. Tarcomnicu, I. Saramet and G. Bancescu, Eur. J. Med. Chem., 44, 4752 (2009); https://doi.org/10.1016/j.ejmech.2009.06.021
  24. M.S. Karthikeyan, Eur. J. Med. Chem., 44, 827 (2009); https://doi.org/10.1016/j.ejmech.2008.04.022
  25. B. Tozkoparan, N. Gokhan, G. Aktay, E. Yeilada and M. Ertan, Eur. J. Med. Chem., 35, 743 (2000); https://doi.org/10.1016/S0223-5234(00)00157-4
  26. J. Ye, Q. Liu, C. Wang, Q. Meng, H. Sun, J. Peng, X. Ma and K. Liu, Pharmacol. Rep., 65, 505 (2013); https://doi.org/10.1016/S1734-1140(13)71026-0
  27. B. Rahmutulla, K. Matsushita, M. Satoh, M. Seimiya, S. Tsuchida, S. Kubo, H. Shimada, M. Ohtsuka, M. Miyazaki and F. Nomura, Oncotarget, 5, 2404 (2014); https://doi.org/10.18632/oncotarget.1650
  28. V. Popsavin, L. Torovic, M. Svirèev, V. Kojic, G. Bogdanovic and V. Popsavin, Bioorg. Med. Chem. Lett., 16, 2773 (2006); https://doi.org/10.1016/j.bmcl.2006.02.001
  29. A. Uzgören-Baran, B.C. Tel, D. Sarigöl, E.I. Oztürk, I. Kazkayasi, G. Okay, M. Ertan and B. Tozkoparan, Eur. J. Med. Chem., 57, 398 (2012); https://doi.org/10.1016/j.ejmech.2012.07.009
  30. R. Pignatello, S. Mazzone, A.M. Panico, G. Mazzone, G. Pennisi, R. Castana, M. Matera and G. Blandino, Eur. J. Med. Chem., 26, 929 (1991); https://doi.org/10.1016/0223-5234(91)90135-A
  31. A.P. Yengoyan, V.A. Pivazyan, E.A. Chazaryan and R.S. Hakobyan, Russ. J. Gen. Chem., 89, 32 (2019); https://doi.org/10.1134/S1070363219010067
  32. R. Lesyk, O. Vladzimirska, S. Holota, L. Zaprutko and A. Gzella, Eur. J. Med. Chem., 42, 641 (2007); https://doi.org/10.1016/j.ejmech.2006.12.006
  33. L. Wei, J. Cheng, Y. Meng, Y. Ren, H. Deng and Y. Guo, Food Chem., 152, 415 (2014); https://doi.org/10.1016/j.foodchem.2013.11.159
  34. I.F. Sevrioukova and T.L. Poulos, Biochemistry, 52, 4474 (2013); https://doi.org/10.1021/bi4005396
  35. I. Novakova, E.A. Subileau, S. Toegel, D. Gruber, B. Lachmann, E. Urban, C. Chesne, C.R. Noe and W. Neuhaus, PLoS One, 9, e86806 (2014); https://doi.org/10.1371/journal.pone.0086806
Read More
Author biographies is not available.
Download
PDF
Statistic
Read Counter : 2 Download : 0