Efficient synthesis of chromenopyridines containing intramolecular hydrogen bonds through a sequential three-component reaction
Tóm tắt
A one-pot sequential reaction of 1,1-bis(methylsulfanyl)-2-nitroethene, diamines, and 3‐formylchromones in EtOH has been developed to afford chromenopyridines. The method is operationally simple and the products are obtained in good yields.
Tài liệu tham khảo
A. Gaspar, M.J. Matos, J. Garrido, E. Uriarte, F. Borges, Chem. Rev. 114, 4960 (2014)
H. Brotz-Oesterhelt, I. Knezevic, S. Bartel, T. Lampe, U. Warnecke-Eberz, K. Ziegelbauer, D. Habich, H. Labischinski, J. Biol. Chem. 278, 39435 (2003)
S. Toshiro, W. Noriko, US Patent 5519030 (1996)
K. Ukawa, T. Ishiguro, H. Kuriki, A. Nohara, Chem. Pharm. Bull. 33, 4432 (1985)
K. Goto, O. Yaoka, T. Oe, PCT Int. Appl., WO 8401711 A1. 19840510 (1984)
K. Goto, O. Yaoka, T. Oe, Chem. Abstr. 101, 116735 (1984)
T.A. Dineen, K. Chen, A.C. Cheng, K. Derakhchan, O. Epstein, J. Esmay, D. Hickman, C.E. Kreiman, I.E. Marx, R.C. Wahit, P.H. Wen, M.M. Weiss, D.A. Whittington, S. Wood, R.T. Fremeau Jr, R.D. White, J. Med. Chem. 57, 9811 (2014)
D.R. Anderson, S. Hegde, E. Reinhard, L. Gomez, W.F. Vernier, L. Lee, S. Liu, A. Sambandam, P.A. Snider, L. Masih, Bioorg. Med. Chem. Lett. 15, 1587 (2005)
H. Nouri, C. Cadiou, L.M. Lawson-Daku, A. Hauser, S. Chevreux, I. Déchamps-Olivier, F. Lachaud, R. Ternane, M. Trabelsi-Ayadi, F. Chuburu, G. Lemercier, Dalton Trans. 42, 12157 (2013)
T.N. Uma Maheswari, P. Shanmugasundaram, J. Pharm. Res. 6, 214 (2013)
İ. Akyol-Salman, D. Leçe-Sertöz, O. Baykal, J. Ocul. Pharmacol. Ther. 23, 280 (2007)
N.M. Evdokimov, A.S. Kireev, A.A. Yakovlenko, M.Y. Antipin, I.V. Magedov, A. Kornienko, J. Org. Chem. 72, 3443 (2007)
A. Shaabani, F. Hajishaabanha, H. Mofakham, A. Maleki, Mol. Divers. 14, 179 (2010)
V.A. Osyanin, D.V. Osipov, Y.N. Klimochkin, Tetrahedron 68, 5612 (2012)
E. Dimitriadou, J. Stephanidou-Stephanatou, C.A. Tsoleridis, D.J. Hadjipavlou-Litina, C. Kontogiorgis, G.E. Kostakis, Tetrahedron 70, 2938 (2014)
M. Yaqub, R. Perveen, Z. Shafiq, H. Pervez, M.N. Tahir, Synlett 23, 1755 (2012)
A.S. Plaskon, O.O. Grygorenko, S.V. Ryabukhin, Tetrahedron 68, 2743 (2012)
A. Rezvanian, A. Alizadeh, Tetrahedron 68, 10164 (2012)
A. Alizadeh, F. Bayat, Helv. Chim. Acta 97, 694 (2014)
A. Alizadeh, F. Bayat, L.G. Zhu, Aust. J. Chem. 67, 949 (2014)
A. Alizadeh, F. Bayat, L.G. Zhu, Synlett 25, 1759 (2014)
A. Alizadeh, R. Ghanbaripour, L.G. Zhu, Tetrahedron 70, 2048 (2014)
A. Alex, D.S. Millan, M. Perez, F. Wakenhut, G.A. Whitlock, Med. Chem. Commun. 2, 669 (2011)
B. Kuhn, P. Mohr, M. Stahl, J. Med. Chem. 53, 2601 (2010)
S.B. Rafi, B.R. Hearn, P. Vedantham, M.P. Jacobson, A.R. Renslo, J. Med. Chem. 55, 3163 (2012)