A facile one-pot four-component synthesis of dihydropyrrol-2-ones using Cl3CCO2H
الموضوعات : Iranian Journal of CatalysisNourallah Hazeri 1 , Malek Taher Maghsoodlou 2 , Sajad Mohamadian-Souri 3 , Mojtaba Lashkari 4 , Majid Ghashang 5
1 - Department of Chemistry, Faculty of Science, University of Sistan and Baluchestan, P. O. Box 98135-674 Zahedan, Iran
2 - Department of Chemistry, Faculty of Science, University of Sistan & Baluchestan, P. O. Box 98135-674 Zahedan, Iran
3 - Department of Chemistry, Faculty of Science, University of Sistan & Baluchestan, P. O. Box 98135-674 Zahedan, Iran
4 - Faculty of Sciences, Najafabad Branch, Islamic Azad University, Najafabad, Esfahan, Iran
5 - Faculty of Sciences, Najafabad Branch, Islamic Azad University, Najafabad, Esfahan, Iran
الکلمات المفتاحية: Aldehyde, amine, Dialkyl acetylenedicarboxylate, Dihydro-2-oxypyrroles,
ملخص المقالة :
A convenient synthesis of different types of polyfunctional dihydropyrrol-2-ones via one-pot four component reactions of formaldehyde, dialkyl acetylenedicarboxylates and amines, catalyzed by trichloroacetic acid (Cl3CCO2H) at room temperature has been investigated. The significant advantages of this synthetic method are mild reaction conditions, available and inexpensive material, short reaction times, good yields, simple work-up.
[1] L. Garuti, M. Roberti, D. Pizzirani, Mini Rev. Med. Chem. 7 (2007) 481-489.
[2] B. Li, M.P.A. Lyle, G. Chen, J. Li, K. Hu, L. Tang, M.A. Alaoui-Jamali, J. Webster, Bioorg. Med. Chem. 15 (2007) 4601-4608.
[3] T. Kawasuji, M. Fuji, T. Yoshinaga, A. Sato, T. Fujiwarab, R. Kiyamaa, Bioorg. Med. Chem. 15 (2007) 5487-5492.
[4] B. Bohner, M. Baumann, U.S. Patent 4220655 (1980).
[5] A.S. Demir, F. Aydigan, I.M. Akhmedov, Tetrahedron Asymm. 13 (2002) 601-605.
[6] T.K. Hinio, T.G. Machida, A.K. Hino, A.Y. Oume, H.M. Hachioji U.S. Patent 4909828 (1990).
[7] J.T. Anders, H. Gorls, P. Langer, Eur. J. Org. Chem. (2004) 1897-1910.
[8] R. Rico, F. Bermejo, Tetrahedron Lett. 37 (1996) 5809-5812.
[9] C. Grunwald, C. Rundfeldt, H.-J. Lankau, T. Arnold, N. Höfgen, R. Dost, U. Egerland, H.J. Hofmann, K. Unverferth, J. Med. Chem. 49 (2006) 1855-1866.
[10] E. Bellur, P. Langer, Tetrahedron Lett. 47 (2006) 2151-2154.
[11] Q. Chen, M.T. Huggins, D.A. Lightner, W. Norona, A.F. McDonagh, J. Am. Chem. Soc. 121 (1999) 9253-9264.
[12] J.O. Brower, D.A. Lightner, A.F. McDonagh, Tetrahedron 57 (2001) 7813-7827.
[13] S. Omura, Y. Sasaki, Y. Iwai, H. Takeshima, J. Antibiot. 48 (1995) 535-548.
[14] T. Agatsuma, T. Akama, S. Nara, S. Matsumiya, R. Nakai, H. Ogawa, S. Otaki, S. Ikeda, Y. Saitoh, Y. Kanda, Org. Lett. 4 (2002) 4387-4390.
[15] Q. Zhu, H. Jiang, J. Li, S. Liu, C. Xia, M. Zhang, J. Comb. Chem. 11 (2009) 685-696.
[16] A.T. Khan, A. Ghosh, M.M. Khan, Tetrahedron Lett. 53 (2012) 2622-2626.
[17] S. Rana, M. Brown, A. Dutta, A. Bhaumik, C. Mukhopadhyay, Tetrahedron Lett. 54 (2013) 1371-1379.
[18] L. Lv, S. Zheng, X. Cai, Z. Chen, Q. Zhu, S. Liu, ACS Comb. Sci. 15 (2013) 183-192.
[19] Q. Zhu, L. Gao, Z. Chen, S. Zheng, H. Shu, J. Li, H. Jiang, S. Liu, Eur. J. Med. Chem. 54 (2012) 232-238.
[20] Y. Han, Q. Wu, J. Sun, C.G. Yan, Tetrahedron 68 (2012) 8539-8544.
[21] Q. Zhu, L. Huang, Z. Chen, S. Zheng, L. Lv, Z. Zhu, D. Cao, H. Jiang, S. Liu, Chem. Eur. J. 19 (2013) 1268-1280.
[22] S.S. Sajadikhah, N. Hazeri, M.T. Maghsoodlou, S.M. Habibi-Khorassani, J. Chin. Chem. Soc. 60 (2013) 1003-1006.
[23] S.S. Sajadikhah, N. Hazeri, M.T. Maghsoodlou, S.M. Habibi-Khorassani, A. Beigbabaei, A.C. Willis, J. Iran. Chem. Soc. 10 (2013) 863-871.
[24] S.S. Sajadikhah, N. Hazeri, Res. Chem. Intermed. 40 (2014) 737-748.
[25] N. Hazeri, S.S. Sajadikhah, M.T. Maghsoodlou, S. Mohamadian-Souri, M. Norouzi, M. Moein, J. Chin. Chem. Soc. 61 (2014) 217-220.
[26] S.S. Sajadikhah, M.T. Maghsoodlou, N. Hazeri, Res. Chem. Intermed. (2013), in press.
[27] S.S. Sajadikhah, M.T. Maghsoodlou, N. Hazeri, Chin. Chem. Lett. 25 (2014) 58-60.
[28] S.S. Sajadikhah, N. Hazeri, M.T. Maghsoodlou, S.M. Habibi-Khorassani, K. Khandan-Barani, J. Chem. Res. (2013) 40-42.
[29] S.S. Sajadikhah, M.T. Maghsoodlou, N. Hazeri, M. Moein, M. Norouzi, S. Mohamadian-Souri, Lett. Org. Chem. 11 (2014) 268-272.
[30] N. Hazeri, S.S. Sajadikhah, M.T. Maghsoodlou, S. Mohamadian-Souri, M. Norouzi, M. Moein, J. Chin. Chem. Soc. 61 (2014) 217-220.
