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Letters in Organic Chemistry

Editor-in-Chief

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

Research Article

Iodine-Mediated Multi-Component Reactions: Readily Access to Tetrazoles and Guanidines

Author(s): Bajivali Shaik, Mohan Seelam, Ramana Tamminana* and Prasad Rao Kammela

Volume 18, Issue 5, 2021

Published on: 28 July, 2020

Page: [382 - 388] Pages: 7

DOI: 10.2174/1570178617999200728212116

Price: $65

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Abstract

Environmentally benign syntheses of One-pot sequential reactions of benzoyl chloride with amines followed by the treatment of molecular I2 reagent under basic conditions provide benzoyl tetrazoles and guanidines in moderate to excellent yields. This one-pot synthesis has several advantages such as mild reaction conditions, short reaction time, convenient workup, high yields, using cheap and readily available reagent molecular Iodine. In addition, functional group tolerance has been explored.

Keywords: Metal free reaction, removal of sulfur, mild reaction conditions, benzoyl derivatives, multicomponent reaction.

Graphical Abstract

[1]
(a) Evindar, G.; Batey, R.A. Org. Lett., 2003, 5(2), 133-136.
[http://dx.doi.org/10.1021/ol027061h] [PMID: 12529123]
(b) Murru, S.; Patel, B.K.; Le Bras, J.; Muzart, J. J. Org. Chem., 2009, 74(5), 2217-2220.
[http://dx.doi.org/10.1021/jo802589d] [PMID: 19183051]
(c) Wu, X.J.; Jiang, R.; Wu, B.; Su, X.M.; Xu, X.P.; Ji, S.J. Adv. Synth. Catal., 2009, 3150.
[http://dx.doi.org/10.1002/adsc.200900481]
(d) Lv, X.; Bao, W. J. Org. Chem., 2009, 74(15), 5618-5621.
[http://dx.doi.org/10.1021/jo900743y] [PMID: 19719252]
(e) Martin, R.E.; Green, L.G.; Guba, W.; Kratochwil, N.; Christ, A. J. Med. Chem., 2007, 50(25), 6291-6294.
[http://dx.doi.org/10.1021/jm701143p] [PMID: 18020390]
(f) Bonfanti, J.F.; Doublet, F.; Fortin, J.; Lacrampe, J.; Guillemont, J.; Muller, P.; Queguiner, L.; Arnoult, E.; Gevers, T.; Janssens, P.; Szel, H.; Willebrords, R.; Timmerman, P.; Wuyts, K.; Janssens, F.; Sommen, C.; Wigerinck, P.; Andries, K. J. Med. Chem., 2007, 50(19), 4572-4584.
[http://dx.doi.org/10.1021/jm070143x] [PMID: 17722899]
(g) Carpenter, A.J.; Al-Barazanji, K.A.; Barvian, K.K.; Bishop, M.J.; Britt, C.S.; Cooper, J.P.; Goetz, A.S.; Grizzle, M.K.; Hertzog, D.L.; Ignar, D.M.; Morgan, R.O.; Peckham, G.E.; Speake, J.D. Bioorg. Med. Chem. Lett., 2006, 16, 4994.
[http://dx.doi.org/10.1016/j.bmcl.2006.07.054] [PMID: 16904318]
[2]
(a) Bae, I.; Han, H.; Chang, S. J. Am. Chem. Soc., 2005, 127(7), 2038-2039.
[http://dx.doi.org/10.1021/ja0432968] [PMID: 15713069]
(b) Cho, S.H.; Yoo, E.J.; Bae, I.; Chang, S. J. Am. Chem. Soc., 2005, 127(46), 16046-16047.
[http://dx.doi.org/10.1021/ja056399e] [PMID: 16287290]
(c) Cassidy, M.P.; Raushel, J.; Fokin, V.V. Angew. Chem. Int. Ed., 2006, 45, 3154.
[http://dx.doi.org/10.1002/anie.200503805]
(d) Cui, S.L.; Lin, X.F.; Wang, Y.G. Org. Lett., 2006, 8(20), 4517-4520.
[http://dx.doi.org/10.1021/ol061685w] [PMID: 16986939]
(e) Cui, S.L.; Wang, J.; Wang, Y.G. Org. Lett., 2007, 9(24), 5023-5025.
[http://dx.doi.org/10.1021/ol702241e] [PMID: 17979278]
(f) Cho, S.H.; Chang, S. Angew. Chem. Int. Ed., 2007, 46, 1897.
[http://dx.doi.org/10.1002/anie.200604358]
(g) Yoo, E.J.; Chang, S. Org. Lett., 2008, 10(6), 1163-1166.
[http://dx.doi.org/10.1021/ol800049b] [PMID: 18288852]
(h) Yoo, E.J.; Ahlquist, M.; Bae, I.; Sharpless, K.B.; Fokin, V.V.; Chang, S. J. Org. Chem., 2008, 73(14), 5520-5528.
[http://dx.doi.org/10.1021/jo800733p] [PMID: 18557650]
(i) Lu, W.; Song, W.Z.; Hong, D.; Lu, P.; Wang, Y.G. Adv. Synth. Catal., 2009, 351, 1768.
[http://dx.doi.org/10.1002/adsc.200900260]
(j) Jin, H.; Xu, X.; Gao, J.; Zhong, J.; Wang, Y. Adv. Synth. Catal., 2010, 352, 347.
[http://dx.doi.org/10.1002/adsc.200900706]
(k) Chen, Z.; Zheng, D.J. Org. Lett., 2011, 13, 848.
[http://dx.doi.org/10.1021/ol102775s]
(l) Kaim, L.E.; Grimaud, L.; Patil, P. Org. Lett., 2011, 13, 1261.
[http://dx.doi.org/10.1021/ol200003u] [PMID: 21294527]
(m) Kumar, M.R.; Park, A.; Park, N.; Lee, S. Org. Lett., 2011, 13(13), 3542-3545.
[http://dx.doi.org/10.1021/ol201409j] [PMID: 21644532]
(n) Ma, D.; Lu, X.; Shi, L.; Zhang, H.; Jiang, Y.; Liu, X. Angew. Chem. Int. Ed., 2011, 50, 1118.
[http://dx.doi.org/10.1002/anie.201005787]
[3]
(a) Zhu, J.; Bienayme, H. Multicomponent Reactions; Zhu, J.; Bienayme, H., Eds.; Wiley, V.C.H.: Weinheim, 2005.
[http://dx.doi.org/10.1002/3527605118]
(b) Ramon, D.J.; Yus, M. Angew. Chem. Int. Ed., 2005, 44, 1602.
[http://dx.doi.org/10.1002/anie.200460548]
(c) Liéby-Muller, F.; Constantieux, T.; Rodriguez, J. J. Am. Chem. Soc., 2005, 127(49), 17176-17177.
[http://dx.doi.org/10.1021/ja055885z] [PMID: 16332052]
(d) Dömling, A. Chem. Rev., 2006, 106(1), 17-89.
[http://dx.doi.org/10.1021/cr0505728] [PMID: 16402771]
(e) Tietze, L.F. Chem. Rev., 1996, 96(1), 115-136.
[http://dx.doi.org/10.1021/cr950027e] [PMID: 11848746]
(f) D’Souza, D.M.; Muller, T.J. J. Chem. Soc. Rev., 2007, 36, 1095.
[http://dx.doi.org/10.1039/B608235C]
(g) Balme, G.; Bossharth, E.; Monteiro, N. Eur. J. Org. Chem., 2003, 4101.
[http://dx.doi.org/10.1002/ejoc.200300378]
(h) Willy, B.; Müller, T.J. Bioorg. Med. Chem. Lett., 2000, 10, 1701.
[4]
(a) Yadav, J.S.; Reddy, B.V.S.; Premalatha, K.; Swamy, T. Tetrahedron Lett., 2005, 46, 2687.
[http://dx.doi.org/10.1016/j.tetlet.2005.02.068]
(b) Huang, G.; Isobe, M. Tetrahedron, 2001, 57, 10241.
[http://dx.doi.org/10.1016/S0040-4020(01)01066-3]
(c) Tsukiyama, T.; Peters, S.C.; Isobe, M. Synlett, 1993, 413.
[http://dx.doi.org/10.1055/s-1993-22476]
(d) Hosokawa, S.; Kirschbaum, B.; Isobe, M. Tetrahedron Lett., 1998, 39, 1917.
[http://dx.doi.org/10.1016/S0040-4039(98)00047-1]
(e) Tsukiyama, T.; Isobe, M. Tetrahedron Lett., 1992, 33, 7911.
[http://dx.doi.org/10.1016/S0040-4039(00)74776-9]
(f) Shen, S.; Xu, X.; Ji, S. Youji Huaxue, 2009, 29, 806.
(g) Zhou, Y.; Yan, P.; Li, G.; Chen, Z. Youji Huaxue, 2009, 29, 1719.
(h) Kim, J.G.; Jang, D.O. Synlett, 2010, 2093.
(i) Zeng, L. J. Comb. Chem., 2010, 12, 35.
[http://dx.doi.org/10.1021/cc9000983] [PMID: 19950908]
[5]
(a) Togo, H.; Iida, S. Synlett, 2006, 2159.
[http://dx.doi.org/10.1055/s-2006-950405]
(b) Banik, B.K.; Fernandez, M.; Alvarez, C. Tetrahedron Lett., 2005, 46, 2479.
[http://dx.doi.org/10.1016/j.tetlet.2005.02.044]
(c) Yadav, J.S.; Reddy, B.V.S.; Shankar, K.S.; Swamy, S.T. Tetrahedron Lett., 2010, 51, 46.
[http://dx.doi.org/10.1016/j.tetlet.2009.10.063]
(d) Lin, X.; Dai, X.; Mao, Z.; Wang, Y. Tetrahedron, 2009, 65, 9233.
[http://dx.doi.org/10.1016/j.tet.2009.09.007]
(e) Jaratjaroonphong, J.; Sathalalai, S.; Techa-sauvapak, P.; Reutrakul, V. Tetrahedron Lett., 2009, 50, 6012.
[http://dx.doi.org/10.1016/j.tetlet.2009.08.036]
(f) Jereb, M.; Vrazic, D.; Zupan, M. Tetrahedron Lett., 2009, 50, 2347.
[http://dx.doi.org/10.1016/j.tetlet.2009.02.224]
(g) Ko, S.; Sastry, M.N.V.; Lin, C.; Yao, C.F. Tetrahedron Lett., 2005, 46, 5771.
[http://dx.doi.org/10.1016/j.tetlet.2005.05.148]
(h) Nath, J.; Ghosh, H.; Yella, R.; Patel, B.K. Eur. J. Org. Chem., 2009, 1849.
[http://dx.doi.org/10.1002/ejoc.200801270]
(i) Nath, J.; Patel, B.K.; Jamir, L.; Sinha, U.B.; Satyanarayana, K.V.V.V. Green Chem., 2009, 11, 1503.
[http://dx.doi.org/10.1039/b914283p]
(j) Ali, A.R.; Ghosh, H.; Patel, B.K. Tetrahedron Lett., 2010, 51, 1019.
[http://dx.doi.org/10.1016/j.tetlet.2009.12.017]
(k) Jiang, B.; Li, C.; Tu, S.J.; Shi, F. J. Comb. Chem., 2010, 12(4), 482-487.
[http://dx.doi.org/10.1021/cc1000192] [PMID: 20491470]
[6]
(a) Xiang, Y.D.; William, P. Synthesis, 1987, 823.
(b) Nardi, A.; Peter Olesen, S.; Christophersen, P. Ion Channels and Transporters of Epithelia in Health and Disease, 2015, 2, 857.
(c) Zhong, D.; Lu, T. Sci. China Chem., 2011, 54, 1395.
[http://dx.doi.org/10.1007/s11426-011-4358-z]
[7]
(a) Hu, J.H.; Wang, L.C. Phosphorus Sulfur Silicon Relat. Elem., 2006, 181, 2691.
[http://dx.doi.org/10.1080/10426500600862878]
(b) Zhang, Y.M.; Wei, T.B.; Xian, L.; Gao, L.M. Phosphorus Sulfur Silicon Relat. Elem., 2004, 179, 2007.
[http://dx.doi.org/10.1080/10426500490473456]
(c) Wei, T.B.; Zhang, Y.M.; Gao, L.M. Synthetic comm., 2009, 30-493.
(d) Rasmussen, C.R.; Villani, F.J., Jr; Weaner, L.E.; Reynolds, B.E.; Hecker, A.R.; Hood, A.R.; Nortey, S.O.; Hanslin, A.; Costanzo, M.J.; Powell, E.T.; Molinari, A.J. Synthesis, 1988, 456.
[http://dx.doi.org/10.1055/s-1988-27605]
(e) Rauf, M.K.; Imtiaz-ud-Din, ; Badshah, A.; Gielen, M.; Ebihara, M.; Vos, Dd.; Ahmed, S. J. Inorg. Biochem., 2009, 103(8), 1135-1144.
[http://dx.doi.org/10.1016/j.jinorgbio.2009.05.014] [PMID: 19570580]
[8]
(a) Jayashree, N.; Latonglila, J.; Bhisma, K.P. Green Chem. Lett. Rev., 2011, 4, 1.
[http://dx.doi.org/10.1080/17518253.2010.486773]
(b) Ganesh, M.; Saroj, K.R.; Srimanta, G.; Anupal, G.; Bhisma, K.P. RSC Advances, 2014, 4, 5357.
[http://dx.doi.org/10.1039/c3ra44897e]
(c) Mekhman, S.; Yusubova, V.V.Z. Resource-Efficient Technologies., 2015, 1, 49.
[http://dx.doi.org/10.1016/j.reffit.2015.06.001]
(d) Mani, R.; Yu, H.W.; Shiuh, T.L. Org. Lett., 2015, 17, 5886.
[http://dx.doi.org/10.1021/acs.orglett.5b03068] [PMID: 26600121]
(e) Lamani, M.; Prabhu, K.R. J. Org. Chem., 2011, 76(19), 7938-7944.
[http://dx.doi.org/10.1021/jo201402a] [PMID: 21866914]
[9]
(a) Ali, A.R.; Ghosh, H.; Patel, B.K. Tetrahedron Lett., 2010, 51, 1019.
[http://dx.doi.org/10.1016/j.tetlet.2009.12.017]
(b) Guin, S.; Rout, S.K.; Gogoi, A.; Nandi, S.; Ghara, K.K.; Patel, B.K. Adv. Synth. Catal., 2012, 354, 2757.
[http://dx.doi.org/10.1002/adsc.201200408]
(c) Yella, R.; Khatun, N.; Rout, S.K.; Patel, B.K. Org. Biomol. Chem., 2011, 9(9), 3235-3245.
[http://dx.doi.org/10.1039/c0ob01007c] [PMID: 21431153]
(d) Pinapati, S.; Mandapati, U.; Rudraraju, R. ChemistrySelect, 2017, 2, 295.
[http://dx.doi.org/10.1002/slct.201601602]
(e) Ramana, T.; Punniyamurthy, T. Chemistry, 2012, 18(42), 13279-13283.
[http://dx.doi.org/10.1002/chem.201202215] [PMID: 22952009]
(f) UshaRani, M.; Srinivasarao, P.; RameshRaju, M.R. Tetrahedron Lett., 2017, 58, 125.
(g) Mohan, S.; Bajivali, S.K.; Prasad Rao, K. Synthetic comm., 2016, 46-1759.
(h) Batey, R.A.; Powell, D.A. Org. Lett., 2000, 2(20), 3237-3240.
[http://dx.doi.org/10.1021/ol006465b] [PMID: 11009390]
(i) Sahoo, S.K.; Jamir, L.; Guin, S.; Patel, B.K. Adv. Synth. Catal., 2010, 352, 2538.
[http://dx.doi.org/10.1002/adsc.201000383]
(j) Jamir, L.; Sinha, U.P.; Nath, J.; Patel, B.K. Synth. Commun., 2012, 42, 951.
[http://dx.doi.org/10.1080/00397911.2010.532276]

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