Efficient synthesis of chromenopyridines containing intramolecular hydrogen bonds through a sequential three-component reaction
Article
First Online:
Received:
Accepted:
- 146 Downloads
- 3 Citations
Abstract
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.
Keywords
1,1-Bis(methylsulfanyl)-2-nitroethene Diamine 3‐Formylchromone Chromenopyridine Intramolecular hydrogen bondNotes
Acknowledgments
Financial support of this research from Tarbiat Modares University, Iran is gratefully acknowledged.
References
- 1.A. Gaspar, M.J. Matos, J. Garrido, E. Uriarte, F. Borges, Chem. Rev. 114, 4960 (2014)CrossRefGoogle Scholar
- 2.H. Brotz-Oesterhelt, I. Knezevic, S. Bartel, T. Lampe, U. Warnecke-Eberz, K. Ziegelbauer, D. Habich, H. Labischinski, J. Biol. Chem. 278, 39435 (2003)CrossRefGoogle Scholar
- 3.S. Toshiro, W. Noriko, US Patent 5519030 (1996)Google Scholar
- 4.K. Ukawa, T. Ishiguro, H. Kuriki, A. Nohara, Chem. Pharm. Bull. 33, 4432 (1985)CrossRefGoogle Scholar
- 5.K. Goto, O. Yaoka, T. Oe, PCT Int. Appl., WO 8401711 A1. 19840510 (1984)Google Scholar
- 6.K. Goto, O. Yaoka, T. Oe, Chem. Abstr. 101, 116735 (1984)Google Scholar
- 7.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)CrossRefGoogle Scholar
- 8.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)CrossRefGoogle Scholar
- 9.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)CrossRefGoogle Scholar
- 10.T.N. Uma Maheswari, P. Shanmugasundaram, J. Pharm. Res. 6, 214 (2013)Google Scholar
- 11.İ. Akyol-Salman, D. Leçe-Sertöz, O. Baykal, J. Ocul. Pharmacol. Ther. 23, 280 (2007)CrossRefGoogle Scholar
- 12.N.M. Evdokimov, A.S. Kireev, A.A. Yakovlenko, M.Y. Antipin, I.V. Magedov, A. Kornienko, J. Org. Chem. 72, 3443 (2007)CrossRefGoogle Scholar
- 13.A. Shaabani, F. Hajishaabanha, H. Mofakham, A. Maleki, Mol. Divers. 14, 179 (2010)CrossRefGoogle Scholar
- 14.V.A. Osyanin, D.V. Osipov, Y.N. Klimochkin, Tetrahedron 68, 5612 (2012)CrossRefGoogle Scholar
- 15.E. Dimitriadou, J. Stephanidou-Stephanatou, C.A. Tsoleridis, D.J. Hadjipavlou-Litina, C. Kontogiorgis, G.E. Kostakis, Tetrahedron 70, 2938 (2014)CrossRefGoogle Scholar
- 16.M. Yaqub, R. Perveen, Z. Shafiq, H. Pervez, M.N. Tahir, Synlett 23, 1755 (2012)CrossRefGoogle Scholar
- 17.A.S. Plaskon, O.O. Grygorenko, S.V. Ryabukhin, Tetrahedron 68, 2743 (2012)CrossRefGoogle Scholar
- 18.A. Rezvanian, A. Alizadeh, Tetrahedron 68, 10164 (2012)CrossRefGoogle Scholar
- 19.A. Alizadeh, F. Bayat, Helv. Chim. Acta 97, 694 (2014)CrossRefGoogle Scholar
- 20.A. Alizadeh, F. Bayat, L.G. Zhu, Aust. J. Chem. 67, 949 (2014)CrossRefGoogle Scholar
- 21.A. Alizadeh, F. Bayat, L.G. Zhu, Synlett 25, 1759 (2014)CrossRefGoogle Scholar
- 22.A. Alizadeh, R. Ghanbaripour, L.G. Zhu, Tetrahedron 70, 2048 (2014)CrossRefGoogle Scholar
- 23.A. Alex, D.S. Millan, M. Perez, F. Wakenhut, G.A. Whitlock, Med. Chem. Commun. 2, 669 (2011)CrossRefGoogle Scholar
- 24.B. Kuhn, P. Mohr, M. Stahl, J. Med. Chem. 53, 2601 (2010)CrossRefGoogle Scholar
- 25.S.B. Rafi, B.R. Hearn, P. Vedantham, M.P. Jacobson, A.R. Renslo, J. Med. Chem. 55, 3163 (2012)CrossRefGoogle Scholar
Copyright information
© Springer Science+Business Media Dordrecht 2016