A facile one-pot four-component synthesis of dihydropyrrol-2-ones using Cl3CCO2H
الموضوعات : Iranian Journal of Catalysis
Nourallah Hazeri
1
(Department of Chemistry, Faculty of Science, University of Sistan and Baluchestan, P. O. Box 98135-674 Zahedan, Iran)
Malek Taher Maghsoodlou
2
(Department of Chemistry, Faculty of Science, University of Sistan & Baluchestan, P. O. Box 98135-674 Zahedan, Iran)
Sajad Mohamadian-Souri
3
(Department of Chemistry, Faculty of Science, University of Sistan & Baluchestan, P. O. Box 98135-674 Zahedan, Iran)
Mojtaba Lashkari
4
(Faculty of Sciences, Najafabad Branch, Islamic Azad University, Najafabad, Esfahan, Iran)
Majid Ghashang
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.
