Efficient one-pot synthesis of 2,3-dihydroquinazoline-4(1H)-ones promoted by FeCl3/neutral Al2O3
Article
First Online:
- 9 Downloads
Abstract
2,3-Dihydroquinazolin-4(1H)-one derivatives have been synthesized via one-pot reaction of isatoic anhydride, aromatic aldehyde, and ammonium acetate catalyzed by FeCl3/neutral Al2O3 in tert-butanol under reflux conditions. Inexpensive and easily available reagents, convenient work-up procedure, reusable catalyst, and moderate to good yield are the salient features of this protocol.
Keywords
2,3-Dihydroquinazolin-4(1H)-one FeCl3/neutral Al2O3 One-pot synthesis Isatoic anhydride AldehydesNotes
Acknowledgements
The project was supported by the Education Department of Hebei Province Foundation for Youths (QN2015039) and the Foundation of Hebei University (no. 799207217002).
Supplementary material
References
- 1.R.J. Alaimo, H.E. Russell, J. Med. Chem. 15, 335 (1972)CrossRefGoogle Scholar
- 2.Z.W. Wang, M.X. Wang, X. Yao, Y. Li, J. Tan, L.Z. Wang, W.T. Qiao, Y.Q. Geng, Y.X. Liu, Q.M. Wang, Eur. J. Med. Chem. 53, 275 (2012)CrossRefGoogle Scholar
- 3.G.M. Chinigo, M. Paige, S. Grindrod, E. Hamel, S. Dakshanamurthy, M. Chruszcz, W. Minor, M.L. Brown, J. Med. Chem. 51, 4620 (2008)CrossRefGoogle Scholar
- 4.R.A. Smits, I.J.P. de Esch, O.P. Zuiderveld, J. Broeker, K. Sansuk, E. Guaita, G. Coruzzi, M. Adami, E. Haaksma, R. Leurs, J. Med. Chem. 51, 7855 (2008)CrossRefGoogle Scholar
- 5.K.I. Ozaki, Y. Yamada, T. Oine, T. Ishizuka, Y. Iwasawat, J. Med. Chem. 28, 568 (1985)CrossRefGoogle Scholar
- 6.S.E. Abbas, F.M. Awadallah, N.A. Ibrahin, E.G. Said, G.M. Kamel, Eur. J. Med. Chem. 53, 141 (2012)CrossRefGoogle Scholar
- 7.M. Shiri, M.M. Heravi, H. Hamidi, M.A. Zolfigol, Z. Tanbakouchian, A. Nejatinezhad-Arani, S.A. Shintre, N.A. Koorbanally, J. Iran. Chem. Soc. 13, 2239 (2016)CrossRefGoogle Scholar
- 8.J.W. Chern, P.L. Tao, K.C. Wang, A. Gutcait, S.W. Liu, M.H. Yen, S.L. Chien, J.K. Rong, J. Med. Chem. 41, 3128 (1998)CrossRefGoogle Scholar
- 9.G. Saravanan, V. Alagarsamy, C.R. Prakash, Bioorg. Med. Chem. Lett. 22, 3072 (2012)CrossRefGoogle Scholar
- 10.H.K. Rhee, J.H. Yoo, E. Lee, Y.J. Kwon, H.R. Seo, Y.S. Lee, H.Y.P. Choo, Eur. J. Med. Chem. 46, 3900 (2011)CrossRefGoogle Scholar
- 11.G. Bonola, P. Da Re, M.J. Magistretti, E. Massarani, I. Setnikar, J. Med. Chem. 11, 1136 (1968)CrossRefGoogle Scholar
- 12.M.J. Hour, L.J. Huang, S.C. Kuo, Y. Xia, K. Bastow, Y. Nakanishi, E. Hamel, K.H. Lee, J. Med. Chem. 43, 4479 (2000)CrossRefGoogle Scholar
- 13.V. Dolle, E. Fan, C.H. Nguyen, A.M. Aubertin, A. Kirn, M.L. Andreola, G. Jamieson, L. Tarrago-Litvak, E. Bisagni, J. Med. Chem. 38, 4679 (1995)CrossRefGoogle Scholar
- 14.J.S. Wai, T.M. Williams, D.L. Bamberger, T.E. Fisher, J.M. Hoffman, R.J. Hudcosky, S.C. MacTough, C.S. Rooney, W.S. Saari, C.M. Thomas, M.E. Goldman, J.A. Obrien, E.A. Emini, J.H. Nunberg, J.C. Quintero, W.A. Schleif, P.S. Andersont, J. Med. Chem. 36, 249 (1993)CrossRefGoogle Scholar
- 15.D.J. Connolly, D. Cusack, T.P. O’Sullivan, P.J. Guiry, Tetrahedron 61, 10153 (2005)CrossRefGoogle Scholar
- 16.V.B. Labade, P.V. Shinde, M.S. Shingare, Tetrahedron Lett. 54, 5778 (2013)CrossRefGoogle Scholar
- 17.J. Safari, S. Gandomi-Ravandi, C. R. Chim. 16, 1158 (2013)CrossRefGoogle Scholar
- 18.M. Ghashang, S.S. Mansoo, K. Aswin, Res. Chem. Intermed. 41, 3447 (2015)CrossRefGoogle Scholar
- 19.M. Desroses, M. Scobie, T. Helleday, New J. Chem. 37, 3595 (2013)CrossRefGoogle Scholar
- 20.J.K. Wang, Y.X. Zong, R.G. Fu, Y.Y. Niu, G.R. Yue, Z.J. Quan, X.C. Wang, Y. Pan, Ultrason. Sonochem. 21, 29 (2014)CrossRefGoogle Scholar
- 21.N. Ramesh, M.G. Rao, R. Varala, V.U. Rao, B.H. Babu, Med. Chem. Res. 25, 1945 (2016)CrossRefGoogle Scholar
- 22.H. Alinezhad, E. Soleymani, M. Zare, Res. Chem. Intermed. 43, 457 (2017)CrossRefGoogle Scholar
- 23.S.G. Zhang, Z.B. Xie, L.S. Liu, M. Liang, Z.G. Le, Chin. Chem. Lett. 28, 101 (2017)CrossRefGoogle Scholar
- 24.M. Abdollahi-Alibeik, E. Shabani, J. Iran. Chem. Soc. 11, 351 (2014)CrossRefGoogle Scholar
- 25.N. Noori, N. Nikoorazm, A. Ghorbani-Choghamarani, Catal. Lett. 147, 204 (2017)CrossRefGoogle Scholar
- 26.B.B.F. Mirjalili, A. Bamoniri, S. Azad, J. Iran. Chem. Soc. 14, 47 (2017)CrossRefGoogle Scholar
- 27.F. Havasi, A. Ghorbani-Choghamarani, F. Nikpour, Microporous Mesoporous Mater. 224, 26 (2016)CrossRefGoogle Scholar
- 28.B. Majumdar, S. Mandani, T. Bhattacharya, D. Sarma, T.K. Sarma, J. Org. Chem. 82, 2097 (2017)CrossRefGoogle Scholar
- 29.Z.H. Zhang, H.Y. Lu, S.H. Yang, J.W. Gao, J. Comb. Chem. 12, 643 (2010)CrossRefGoogle Scholar
- 30.M.Z. Kassaee, S. Rostamizadeh, N. Shadjou, E. Motamedi, M. Esmaeelzadeh, J. Heterocycl. Chem. 47, 1421 (2010)CrossRefGoogle Scholar
- 31.M. Narasimhulu, Y.R. Lee, Tetrahedron 67, 9627 (2011)CrossRefGoogle Scholar
- 32.A. Ghorbani-Choghamarani, T. Taghipour, Lett. Org. Chem. 8, 470 (2011)CrossRefGoogle Scholar
- 33.K. Niknam, N. Jafarpour, E. Niknam, Chin. Chem. Lett. 22, 69 (2011)CrossRefGoogle Scholar
- 34.K. Niknam, M.R. Mohammadizadeh, S. Mirzaee, Chin. J. Chem. 29, 1417 (2011)CrossRefGoogle Scholar
- 35.M. Wang, T.T. Zhang, Y. Liang, J.J. Gao, Chin. Chem. Lett. 22, 1423 (2011)CrossRefGoogle Scholar
- 36.J. Safari, S. Gandomi-Ravandi, J. Mol. Catal. A Chem. 371, 135 (2013)CrossRefGoogle Scholar
- 37.H.R. Shaterian, N. Fahimi, K. Azizi, Res. Chem. Intermed. 40, 1879 (2014)CrossRefGoogle Scholar
- 38.B.H. Chen, J.T. Li, G.F. Chen, Ultrason. Sonochem. 23, 59 (2015)CrossRefGoogle Scholar
- 39.D.E. Bergbreiter, J.J. Lalonde, J. Org. Chem. 52, 1601 (1987)CrossRefGoogle Scholar
- 40.T.S. Li, H.Y. Duan, B.Z. Li, B.B. Tewari, S.H. Li, J. Chem. Soc. Perkin Trans. 1, 291 (1999)CrossRefGoogle Scholar
- 41.M. Salavati-Niasari, J. Hasanalian, H. Najafian, J. Mol. Catal. A Chem. 209, 209 (2004)CrossRefGoogle Scholar
- 42.M. Salavati-Niasari, T. Khosousi, S. Hydarzadeh, J. Mol. Catal. A Chem. 235, 150 (2005)CrossRefGoogle Scholar
- 43.Y. Jiang, J.Y. Wang, J.H. Chen, W.J. Wang, H. Yan, X.X. Zhang, C. Wang, G.L. Zhang, B.G. Li, Acta Chim. Sin. 65, 1925 (2007)Google Scholar
- 44.H. Azimzadeh, A. Akbari, M.R. Omidkhah, Chem. Eng. J. 320, 189 (2017)CrossRefGoogle Scholar
- 45.G.F. Chen, X.Y. Dong, F.Z. Meng, B.H. Chen, J.T. Li, S.X. Wang, G.Y. Bai, Lett. Org. Chem. 8, 464 (2011)CrossRefGoogle Scholar
- 46.G.F. Chen, H.M. Jia, L.Y. Zhang, B.H. Chen, J.T. Li, Ultrason. Sonochem. 20, 627 (2013)CrossRefGoogle Scholar
- 47.G.F. Chen, H.D. Shen, H.M. Jia, L.Y. Zhang, H.Y. Kang, Q.Q. Qi, B.H. Chen, J.L. Cao, J.T. Li, Aust. J. Chem. 66, 262 (2013)CrossRefGoogle Scholar
- 48.G.F. Chen, H.Y. Li, N. Xiao, B.H. Chen, Y.L. Song, J.T. Li, Z.W. Li, Aust. J. Chem. 67, 1516 (2014)CrossRefGoogle Scholar
- 49.G.F. Chen, N. Xiao, J.S. Yang, H.Y. Li, B.H. Chen, L.F. Han, Res. Chem. Intermed. 41, 5159 (2015)CrossRefGoogle Scholar
Copyright information
© Springer Nature B.V. 2019