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
[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]
[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]
[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.
[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]
[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]
(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]
[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]
[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]
[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]