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Letters in Organic Chemistry

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ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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Research Article

Synthesis of Fused Heterocyclic Compounds by Using Formamide Derivatives as C1 Source in the Presence of Mukaiyama Reagent as the Catalyst

Author(s): Ehsan Ghonchepour*, Mohammad Reza Islami and Vajihe Nejadshafiee*

Volume 20, Issue 9, 2023

Published on: 17 May, 2023

Page: [837 - 844] Pages: 8

DOI: 10.2174/1570178620666230414124830

Price: $65

Abstract

An efficient one-pot synthesis of the benzimidazoles and benzothiazole has been developed from the reaction between 1,2 phenylenediamine and 2-aminothiophenol compounds via DMF and DEF as C1 source in the presence of Mukaiyama Reagent (CMPI) as a new organocatalyst. This method was designed based on the principle of green chemistry to avoid the use of any expensive and toxic transition-metal catalyst. All products were known and characterized by FT-IR, CHNS, 1H and 13C NMR data, and also were compared with their physical data with those reported in the literature.

Keywords: Mukaiyama reagent, catalyst, O-phenylenediamine, benzimidazoles, benzothiazole, DMF, polyphosphoric acid.

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[1]
Furtado, L.F.V.; de Paiva Bello, A.C.P.; Rabelo, É.M.L. Acta Trop., 2016, 162, 95-102.
[http://dx.doi.org/10.1016/j.actatropica.2016.06.021] [PMID: 27338184]
[2]
Preston, P. Benzimidazoles Cogeneric Tricyclic Compounds, 1981, (Part 1), 40.
[3]
Choi, S.J.; Park, H.J.; Lee, S.K.; Kim, S.W.; Han, G.; Choo, H.Y.P. Bioorg. Med. Chem., 2006, 14(4), 1229-1235.
[http://dx.doi.org/10.1016/j.bmc.2005.09.051] [PMID: 16242334]
[4]
Saha, P.; Ramana, T.; Purkait, N.; Ali, M.A.; Paul, R.; Punniyamurthy, T. J. Org. Chem., 2009, 74(22), 8719-8725.
[http://dx.doi.org/10.1021/jo901813g] [PMID: 19908912]
[5]
Zhang, J.; Wang, J.L.; Zhou, Z.M.; Li, Z.H.; Xue, W.Z.; Xu, D.; Hao, L.P.; Han, X.F.; Fei, F.; Liu, T.; Liang, A.H. Bioorg. Med. Chem., 2012, 20(14), 4208-4216.
[http://dx.doi.org/10.1016/j.bmc.2012.05.056] [PMID: 22727371]
[6]
Keri, R.S.; Hiremathad, A.; Budagumpi, S.; Nagaraja, B.M. Chem. Biol. Drug Des., 2015, 86(1), 19-65.
[http://dx.doi.org/10.1111/cbdd.12462] [PMID: 25352112]
[7]
Rathee, P.S.; Dhankar, R.; Bhardwaj, S.; Gupta, M.; Kumar, R. J. Appl. Pharm. Sci., 2011, 4, 127.
[8]
Phillips, M.A. J. Chem. Soc., 1928, 0(0), 2393-2399.
[http://dx.doi.org/10.1039/JR9280002393]
[9]
DeLuca, M.R.; Kerwin, S.M. Tetrahedron, 1997, 53(2), 457-464.
[http://dx.doi.org/10.1016/S0040-4020(96)01009-5]
[10]
Fairley, T.A.; Tidwell, R.R.; Donkor, I.; Naiman, N.A.; Ohemeng, K.A.; Lombardy, R.J.; Bentley, J.A. J. Med. Chem., 1993, 36, 1746-1753.
[http://dx.doi.org/10.1021/jm00064a008] [PMID: 8510102]
[11]
Hein, D.W.; Alheim, R.J.; Leavitt, J.J. J. Am. Chem. Soc., 1957, 79(2), 427-429.
[http://dx.doi.org/10.1021/ja01559a053]
[12]
Tidwell, R.R.; Geratz, J.D.; Dann, O.; Volz, G.; Zeh, D.; Loewe, H. J. Med. Chem., 1978, 21(7), 613-623.
[http://dx.doi.org/10.1021/jm00205a005] [PMID: 671460]
[13]
Ravi, V.; Ramu, E.; Vijay, K.; Srinivas Rao, A. Chem. Pharm. Bull., 2007, 55(8), 1254-1257.
[http://dx.doi.org/10.1248/cpb.55.1254] [PMID: 17409557]
[14]
Zhang, Z.H.; Yin, L.; Wang, Y.M. Catal. Commun., 2007, 8(7), 1126-1131.
[http://dx.doi.org/10.1016/j.catcom.2006.10.022]
[15]
Zhou, L.; Wang, Y.; Liu, Z.; Huang, Q. J. Hazard. Mater., 2009, 161(2-3), 995-1002.
[http://dx.doi.org/10.1016/j.jhazmat.2008.04.078] [PMID: 18538924]
[16]
Kattimani, P.P.; Kamble, R.R.; Meti, G.Y. RSC Advances, 2015, 5(37), 29447-29455.
[http://dx.doi.org/10.1039/C5RA00021A]
[17]
Chari, M.A.; Sadanandam, P.; Shobha, D.; Mukkanti, K. J. Heterocycl. Chem., 2010, 47, 153-155.
[18]
Srinivas, U.; Srinivas, C.; Narender, P.; Rao, V.J.; Palaniappan, S. Catal. Commun., 2007, 8(1), 107-110.
[http://dx.doi.org/10.1016/j.catcom.2006.05.022]
[19]
Eynde, J.J.V.; Delfosse, F.; Mayence, A.; Van Haverbeke, Y. Tetrahedron, 1995, 51, 6511-6516.
[http://dx.doi.org/10.1016/0040-4020(95)00318-3]
[20]
Navarrete-Vázquez, G. Bioorg. Med. Chem. Lett., 2006, 16, 4169-4173.
[PMID: 16784847]
[21]
Nagawade, R.R.; Shinde, D.B. Chin. Chem. Lett., 2006, 17, 89-94.
[22]
Bhor, M.D.; Bhanage, B.M. Synth. Commun., 2010, 40(12), 1743-1749.
[http://dx.doi.org/10.1080/00397910903161728]
[23]
Du, L.H.; Wang, Y.G. Synthesis, 2007, 675, 675-678.
[24]
Saha, D.; Saha, A.; Ranu, B.C. Green Chem., 2009, 11(5), 733-737.
[http://dx.doi.org/10.1039/b823543k]
[25]
Itoh, T.; Nagata, K.; Ishikawa, H.; Ohsawa, A. Heterocycles, 2004, 63, 2769-2775.
[http://dx.doi.org/10.3987/COM-04-10215]
[26]
Ruiz, V.R.; Corma, A.; Sabater, M.J. Tetrahedron, 2010, 66(3), 730-735.
[http://dx.doi.org/10.1016/j.tet.2009.11.048]
[27]
Bhatnagar, I.; George, M.V. Tetrahedron, 1968, 24(3), 1293-1298.
[http://dx.doi.org/10.1016/0040-4020(68)88080-9]
[28]
Désaubry, L.; Wermuth, C.G.; Bourguignon, J.J. Tetrahedron Lett., 1995, 36(24), 4249-4252.
[http://dx.doi.org/10.1016/0040-4039(95)00734-T]
[29]
Nale, D.B.; Bhanage, B.M. Synlett, 2015, 26, 2835-2842.
[http://dx.doi.org/10.1055/s-0035-1560319]
[30]
Gao, X.; Yu, B.; Mei, Q.; Yang, Z.; Zhao, Y.; Zhang, H.; Hao, L. New J. Chem., 2016, 40, 8282-8287.
[http://dx.doi.org/10.1039/C6NJ01721E]
[31]
Zhu, J.; Zhang, Z.; Miao, C.; Liu, W.; Sun, W. Tetrahedron, 2017, 73(25), 3458-3462.
[http://dx.doi.org/10.1016/j.tet.2017.05.018]
[32]
Mostafavi, H.; Islami, M.R.; Ghonchepour, E.; Tikdari, A.M. Chem. Pap., 2018, 72(12), 2973-2978.
[http://dx.doi.org/10.1007/s11696-018-0540-5]
[33]
Kalidas, B. Catal. Today, 2018, 309, 51-60.

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