Oxidative aromatization of some 1,4-dihydropyridines by aqueous hydrogen peroxide in ethanol

Abdoli, Masoomeh; Hajibabaiee, Maryam

Document Type : Original Research Article

Authors

¹ Azad university of arak

² Islamic Azad University-Arak Branch. Arak, Iran

Abstract

Some 3, 5-diacyl or 3,5-diester 1,4-dihydropyridines were oxidized to the corresponding pyridine derivatives using hydrogen peroxide in aqueous ethanol in the presence of potassium bromide and acetic acid as the catalysts. The reaction was carried out in ethanol and products were isolated in high to excellent yields. However, oxidation of 3,5-diacetyl 1,4-dihydropyridines is slower than 3,5-diester 1,4-dihydropyridines under the same condition. Furhermore, the reaction is facilitated by electron releasing groups on 4-substituent of dihydropyridine ring. The cheapness of reagent, high yielding, easy workup and mild condition makes this method a useful addition to the available method in organic synthesis. In addition, employment of clean oxidant H2O2 together with nontoxic solvent ethanol makes it friendly to the environment.

Graphical Abstract

Keywords

Main Subjects

Organic chemistry

References

[1] U. Eisner, J. Kuthan, Chem. Rev., 1972, 72, 1-42.

[2] J. Kuthan, A. Kurfürst, Ind. Eng. Chem. Prod. Res. Dev., 1982, 21, 191-261.

[3] D.M. Stout, A.I. Meyers, Chem. Rev., 1982, 82, 223-243.

[4] R. Lavilla, J. Chem. Soc. Perkin Trans 2, 2002, 1, 1141-1156.

[5] R.H. Böcker, F.P.Guengerich, J. Med. Chem., 1986, 29, 1596-1603.

[6] F.P. Guengerich, W.R. Barian, M. Iwasaki, Sari, C. Bäärnhielm, P. Berntsson, J. Med. Chem.,1991, 34, 1838-1844.

[7] H.R. Memarian, M. Abdoli-Senejani, D. Döpp, J. Chin. Chem. Soc., 2007, 54, 131-139.

[8] H.R. Memarian, M. Abdoli-Senejani, S. Tangestaninejad, J. Iran Chem. Soc., 2006, 3, 285-292.

[9] H.R. Memarian, M. Abdoli-Senejani, Ultrason. Sonochem., 2008, 15, 110-114.

[10] H.R. Memarian, H. Sabzyan, M. Abdoli-Senejani, J Mol Struct. (Theochem), 2007, 813, 39-47.

[11] H.R. Memarian, M. Abdoli-Senejani, D. Döpp, Z. Naturforsch., 2006, 61b, 50-56.

[12] M. Abdoli-Senejani, A.A. Taherpour, H.R. Memarian, M. Khosravani, Struct. Chem., 2013, 24, 191-200.

[13] S. Hara, N. Fukasaku, T. Watanabe, A. Ohta, Chem. Pharm. Bull., 1980, 28, 1641-1644.

[14] D. Shahabi, M. A. Amrollahi, A. A. Jafari, J. Iran. Chem,. Soc., 2011, 8, 1052-1057.

[15] S. Das-Sharma, P. Hazarika, D. Konwar, Catal. Commun., 2008, 9,709-714.

[16] M. Filipan-Litvic, M. Litvic, V. Vinkovic, Tetrahedron, 2008, 64, 5649-5656.

[17] A.R. Momeni, H. Aliyan, H. Mombeini, A.R. Massah, H. J. Naghash, Z. Naturforsch., 2006, 61b, 331-333.

[18] Z.Y. Chen, W. Zhang, Chin. Chem. Lett., 2007, 18, 1443-1446.

[19] L. Dagnino, M.C. Li- Kwong-Ken, M.W. Wolowyk, H. Wynn, C. R. Triggle, E.E. Knaus, J. Med. Chem., 1986, 29, 2524-2529.

[20] W. Yutaka, S. Kazuhiro, H. Tomonori; O. Shoichiro, Synthesis, 1983, 761-762.

[21] H.R. Memarian, M. Bagheri, D. Döpp, Monatsh. Chem., 2004, 135, 833-838.

[22] G.W. Wang, J.J. Xia, C.B. Miao, X.L. Wu, Bull. Chem. Soc. Japan., 2006, 79 (3), 454-459.

[23] J.J.V. Eynde, F. Delfosse, A. Mayence, Y. V. Haverbeke, Tetrahedron, 1995, 51, 6511-6516.

[24] B. Love, K.M. Snader, J. Org. Chem., 1965, 30, 1914-1919.

[25] S.H. Mashraqui, M.A. Karnik, Synthesis, 1998, 5, 713-714.

[26] R.S. Varma, D. Kumar, Tetrahedron Lett., 1999, 40, 21-24.

[27] M. Balogh, I. Hermecz, Z. Mészaros, P. Lazlo, Helv. Chim. Acta, 1984, 67, 2270-2272.

Iranian chemical communication

Oxidative aromatization of some 1,4-dihydropyridines by aqueous hydrogen peroxide in ethanol

References

References

Volume 3, Issue 2, pp. 72-147, Serial No. 7
April 2015
Pages 143-147

Oxidative aromatization of some 1,4-dihydropyridines by aqueous hydrogen peroxide in ethanol

References

References

Volume 3, Issue 2, pp. 72-147, Serial No. 7April 2015Pages 143-147

Volume 3, Issue 2, pp. 72-147, Serial No. 7
April 2015
Pages 143-147