Tetramethylguanidiniumtriflate catalyzed Henry reaction of isatins: An efficient synthesis of 3-hydroxy-3-(nitromethyl)indolin-2-one derivatives and their anti-diabetic activity
Subject Areas : Iranian Journal of Catalysis
Leila Youseftabar-Miri
1
(Department of Chemistry, Izeh Branch, Islamic Azad University, Izeh, Iran)
Maryam Rafieirad
2
(Department of Biology, Izeh Branch, Islamic Azad University, Izeh, Iran)
Keywords:
Abstract :
[1] (a) T. Ratan Bal, B. Anand, P. Yogeeswari, D.H. Sriram, Bioorg. Med. Chem. Lett. 15 (2005) 4451–4455. (b) T. Jiang, K.L. Kuhen, K. Wolff, H. Yin, K. Ieza, J. Caldwell, B. Bursulaya, T.Tuntland, K. Zhang, D. Karanewsky, Y. He, Bioorg. Med. Chem. Lett. 16 (2006) 2109–2112.
[2] R. Tripathy, A. Reiboldt, P.A. Messina, M. Iqbal, J. Singh, E.R. Bacon, S. Angeles, Sh.X. Yang, M.S. Albom, C. Robinson, H. Chang, B.A. Ruggeri, J.P. Mallamo, Bioorg. Med. Chem. Lett. 16 (2006) 2158–2162.
[3] (a) A. Cane, M.C. Tournaire, D. Barritault, M. Crumeyrolle-Arias, Biochem. Biophys. Res. Commun. 276 (2000) 379–384. (b) V.C. Silveira, J.S. Luz, C.C. Oliveira, I. Graziani, M.R. Ciriolo, A.M. C. Ferreira, J. Inorg. Biochem. 102 (2008) 1090–1103.
[4] (a) A. Amal Raj, R. Raghunathan, M.R. Sridevikumaria, N. Raman, Bioorg. Med. Chem. 11 (2003) 407–419. (b) M.C. Rodriguez-Arguelles, S. Mosquera-Vazaquez, P. Touron-Touceda, J. Sanmartin-Matalobos, A.M. Garcia-Deibe, M. Belicchi-Ferraris, G. Pelosi, C. Pelizzi, F.J. Zani, J. Inorg. Biochem. 101 (2007) 138–147.
[5] L. Maskell, E.A. Blanche, M.A. Colucci, J.L. Whatmore, Ch. Moody J. Bioorg. Med. Chem. Lett. 17 (2007) 1575–1578.
[6] (a) R. Shimazawa, M. Kuriyama, R. Shirai, R. Bioorg. Med. Chem. Lett. 18 (2008) 3350–3353.
(b) A.H. Abadi, S.M. Abou-Seri, D.E. Abdel-Rahman, Ch. Klein, O. Lozach, L. Meijer, Eur. J. Med. Chem. 41(2006) 296–305.
[7] (a) Y. Yamada, M. Kitajima, N. Kogure, H. Takayama, Tetrahedron 64 (2008) 7690–7694.
(b) N. Kogure, H. Kobayashi, N. Ishii, M. Kitajima, S. Wongseripipatana, H. Takayama, Tetrahedron Lett. 49 (2008) 3638–3642. (c) Z. Zhang, Y. T. Di, Y. T. Wang, S. Z. Mu, X. Fang, Y. Zhang, C. J. Tan, Q. Zhang, X. H.Yan, J. Guo, Tetrahedron 65 (2009) 4551–4556. (d) T.S. Kam, Y.M. Choo, Tetrahedron 56 (2000) 6143–6150. (e) Y. Wu, M. Kitajima, N. Kogure, R. Zhang, H. Takayama, Tetrahedron Lett. 49 (2008) 5935–5938.
[8] W.J. Skiles, D. McNeil, R.B. Labroo, E.A. Cohen, J. Org. Chem. 64 (1999) 1369-1371.
[9] (a) J.I. Jimenez, U. Huber, R.E. Moore, G.M.L. Patterson, J. Nat. Prod. 62 (1999) 569-572. (b) H.B. Rasmussen, J.K. MacLeod, J. Nat. Prod. 60 (1997) 1152-1154. (c) T. Tokunaga, W.E. Hume, T. Umezome, K. Okazaki, Y. Ueki, K. Kumagai, S. Hourai, J. Nagamine, H. Seki, M. Taiji, H. Noguchi, R. Nagata, J. Med. Chem. 44 (2001) 4641-4649. (d) J. Nagamine, R. Nagata, H. Seki, N. Nomura-Akimaru, Y. Ueki, K. Kumagai, M. Taiji, H. Noguchi, J. Endocrinol. 171 (2001) 481-489.
[10] (a) F. Imre, N. Miklo's, S. Aron, B. Ga'bor, T. La'szlo', Tetrahedron 57 (2001) 1129-1137. (b) D.R. Long, C.G. Richards, M.S.F. Ross, J. Hetrocycl. Chem. 15 (1978) 633-677. (c) F.A. Luzziao, Tetrahedron 57 (2001) 915-1138.
[11] L. Liu, S. Zhang, F. Xue, G. Lou, H. Zhang, S. Ma, W. Duan, Chem. Eur. J. 17 (2011) 1791-1795.
[12] G. Chen, Y. Wang, H. He, S. Gao, X. Yang, X. Hao, Heterocycles 68 (2006).2327–2333.
[13] W.R. Conn, H.G. Lindwall, J. Am. Chem. Soc. 58 (1936) 1236–1239.
[14] G. Chen, X-J. Hao, Q-Y. Sun, J. Ding, Chemical Papers 64 (2010) 673-677.
[15] H.M. Meshram, Palakuri Ramesh, A. Sanjeeva Kumar, A. Swetha, Tetrahedron Lett. 52 (2011) 5862–5864.
[16] H.M. Meshram, B.P. Thakur, M.B. Bejjam, V.M. Bangade, Green Chem. Lett. & Rev. 6 (2013) 19-43.
[17] M.N. Elinson, A.I. Ilovaisky, V.M. Merkulova, F. Barba, B. Batanero, B. Tetrahedron 64 (2008) 5915–5919.
[18] (a) P. Wasserscheid, T. Welton, Ionic Liquids in Synthesis; Wiley-VCH Verlag: Stuttgart, Germany, 2002. (b) M. Fremantle, Chem. Eng. News 76 (1998) 32-37.
[19] N.M.M. Mateus, L.C. Branco, N.M.T. Lourenco, C.A.M. Afonso, Green Chem. 5 (2003) 347–352.
[20] (a) K. Rad-Moghadam, L. Youseftabar-Miri, J. Florin. Chem. 135 (2012) 213-219. (b) H. Hosseinjani-Pirdehi, K. Rad-Moghadam, L. Youseftabar-Miri, Tetrahedron 70 (2014) 1780-1785. (c) K. Rad-Moghadam, L. Youseftabar-Miri, Arkivoc XI (2011) 43-50. (d) K. Rad-Moghadam, L. Youseftabar-Miri, Tetrahedron 67 (2011) 5693-5699
[21] E. Hosseini, K. Karimzadeh, M. Vessal, M. Rafieirad, HealthMED. J. 612 (2012) 4253-4257.
[22] S. Lenzen, Diabetologia 51 (2008) 216-226.
