Abstract
An efficient and direct procedure for the synthesis of pyrido[2,3-d:6,5-d′]dipyrimidine derivatives has been described under microwave-assisted conditions. The reaction of 2-thiobarbituric acid with aromatic aldehydes and ammonium acetate catalyzed by CuFe2O4 nanoparticles was resulted in the formation of pyrido[2,3-d:6,5 d′]dipyrimidine derivatives. The corresponding products have been obtained in excellent isolated yields with high purity, in short reaction times and easy workup.
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M. Mohsenimehr, M. Mamaghani, F. Shirini, M. Sheykhan, F. Azimian Moghaddam, Chin. Chem. Lett. 25, 1387 (2014)
L. Yang, D. Shi, S. Chen, H. Chai, D. Huang, Q. Zhanga, J. Li, Green Chem. 14, 945 (2012)
T.P. Selvam, C.R. James, P.V. Dniandev, S.K. Valzita, Res. Pharm 2, 1 (2012)
J.W. Ellingboe, N.J. Princeton, Chem. Abstr. 124, 176134q (1996)
V.E. Kolla, A.B. Deyanov, F.Y. Nazmetdinov, Z.N. Kashina, L.P. Drovosekova, Pharm. Chem. J. 27, 635 (1993)
A. Agarwal, N. Goyal, P. Chauhan, S. Gupta, Bioorg. Med. Chem. 13, 6678 (2005)
A.D. Broom, J.L. Shim, G.L. Anderson, J. Org. Chem. 41, 1095 (1976)
A. Rosowsky, C.E. Mota, S.F. Queener, J. Heterocycl. Chem. 32, 335 (1995)
V.E. Kolla, A.B. Deyanov, F.Y. Nazmetdinov, Z.N. Kashina, L.P. Drovosekova, Pharm. Chem. J. 27, 635 (1993)
I.O. Donkor, C.L. Klein, L. Liang, N. Zhu, E. Bradley, A.M. Clark, J. Pharm. Sci. 84, 661 (1995)
A.B. Deyanov, R.K. Niyazov, F.Y. Nazmetdivov, B.Y. Syropyatov, V.E. Kolla, M.E. Konshin, Pharm. Chem. J. 25, 248 (1991)
R.K. Rawal, R. Tripathi, S.B. Katti, C. Pannecouquec, E.D. Clercq, Bioorg. Med. Chem. 15, 3134 (2007)
I.D. Bystryakova, O.A. Burova, G.M. Chelysheva, S.V. Zhilinkova, N.M. Smirnova, T.S. Safonova, Pharm. Chem. J. 25, 874 (1991)
K. Furukawa, T. Hasegawa, Chem. Abst. 124, 289568c (1996)
A. Monge, V. Martinez-Merino, C. Sanmartin, F.J. Fernandez, M.C. Ochoa, C. Berllver, P. Artigas, E. Fernandez-Alvarez, Eur. J. Med. Chem. 24, 209 (1989)
E.M. Grivsky, S. Lee, C.W. Sigel, D.S. Duch, C.A. Nichol, J. Med. Chem. 23, 327 (1980)
N. Kammasud, C. Boonyarat, K. Sanphanya, M. Utsintong, S. Tsunoda, H. Sakurai, I. Saiki, I. André, D.S. Grierson, O. Vajragupta, Bioorg. Med. Chem. Lett. 19, 745 (2009)
I.D. Bystryakova, O.A. Burova, G.M. Chelysheva, S.V. Zhilinkova, N.M. Smirnova, T.S. Safonova, Pharm. Chem. J. 25, 874 (1991)
A. Pastor, R. Alajarin, J.J. Vaquero, J. Alvarez-Builla, M.F. Casa-Juana, C. Sunkel, J.G. Priego, I. Fonseca, J. Sanz-Aparicio, Tetrahedron 50, 8085 (1994)
A.M. Thompson, A.J. Bridges, D.W. Fry, A.J. Kraker, W.A. Denny, J. Med. Chem. 38, 3780 (1995)
B. Jiang, L. Xue, X. Wang, M. Tu, Y. Liu, Sh Tu, Tetrahedron Lett. 53, 1261 (2012)
S. Chaudhary, W. Harding, Tetrahedron 67, 569 (2011)
S. Mohan, B. Kumar, S. Dinda, D. Naik, S. Prabu Seenivasan, V. Kumar, D. Rana, P. Brahmkshatriy, Bioorg. Med. Chem. Lett. 22, 7539 (2012)
A. Dela Hoz, A. Díaz-Ortiz, A. Moreno, Chem. Soc. Rev. 34, 164 (2005)
A. Dolzhenko, S. Kalinina, D. Kalinin, RSC Adv. 3, 15853 (2013)
R. Ghahremanzadeh, Z. Rashid, A.H. Zarnani, H. Naeimi, J. Ind. Eng. Chem. 20, 4076 (2014)
I. Tellitu, I. Beitia, M. Díaz, A. Alonso, I. Moreno, E. Domínguez, Tetrahedron 71, 8251 (2015)
Q. Du, W. Zhang, H. Ma, J. Zheng, B. Zhou, Y. Li, Tetrahedron 68, 3577 (2012)
R. Parella, Naveen, A. Kumar, S. Arulananda, Babu. Tetrahedron Lett. 54, 1738 (2013)
R. Ghahremanzadeh, Z. Rashid, A.H. Zarnani, H. Naeimi, Appl. Catal. A 467, 270 (2013)
S. Tao, F. Gao, X. Liu, O.T. Sørensen, Mater. Sci. Eng. 77, 172 (2000)
R.K. Rawal, R. Tripathi, S.B. Katti, C. Pannecouquec, E.D. Clercq, Bioorg. Med. Chem. 15, 3134 (2007)
S. Tao, F. Gao, X. Liu, O.T. Sørensen, Mater. Sci. Eng. 77, 172 (2000)
R. Ghahremanzadeh, Z. Rashid, A.H. Zarnani, H. Naeimi, J. Iran. Chem. Soc. 11, 1407 (2014)
A. Bazgir, M. Moammadi Khanaposhtani, R. Ghahremanzadeh, A. Abolhasani Soorki, C. R. Chim 12, 1287 (2009)
R.K. Rawal, R. Tripathi, S.B. Katti, C. Pannecouquec, E.D. Clercq, Bioorg. Med. Chem. 15, 3134 (2007)
N. Azizi, A. Mobinikhaledi, A. Khajeh Amiri, H. Ghafuri, Res. Chem. Intermed. 38, 2271 (2012)
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The authors are grateful to University of Kashan for supporting this work by Grant No. 159148/74.
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Naeimi, H., Didar, A. & Rashid, Z. Microwave-assisted synthesis of pyrido-dipyrimidines using magnetically CuFe2O4 nanoparticles as an efficient, reusable, and powerful catalyst in water. J IRAN CHEM SOC 14, 377–385 (2017). https://doi.org/10.1007/s13738-016-0986-8
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DOI: https://doi.org/10.1007/s13738-016-0986-8