Chinese Journal of Organic Chemistry >
Synthesis of 2,3,8,9-Tetrahydropyrido[2,3-d:6,5-d']dipyrimidine-4,6-diones
Received date: 2012-08-31
Revised date: 2012-09-19
Online published: 2012-09-26
Supported by
Project supported by the Science and Technology Innovation Program of Beijing Institute of Technology (No. 2011CX0436).
2,3,8,9-Tetrahydropyrido[2,3-d:6,5-d']dipyrimidine-4,6-diones were synthesized by using malononitrile, ortho-triethyl and pyridine as starting materials in three steps reaction including cyclization, ammonolysis and reaction with ketones under the catalysis of sodium methoxide. The structures of the products were confirmed by NMR, IR, ESI and elemental analysis.
Key words: pyridodipyrimidinediones; heterocycle; synthesis
Yang Liupan , Li Jiarong , Chai Hongxin , Yuan Hong , Zhang Qi , Shi Daxin . Synthesis of 2,3,8,9-Tetrahydropyrido[2,3-d:6,5-d']dipyrimidine-4,6-diones[J]. Chinese Journal of Organic Chemistry, 2013 , 33(01) : 174 -177 . DOI: 10.6023/cjoc201208039
[1] (a) Lichtenthaler, F. W. Acc. Chem. Res. 2002, 35, 728.
(b) Wang, H. Y.; Zou, Y.; Tao, C. Z. Chin. J. Org. Chem. 2011, 31, 2161 (in Chinese). (王慧彦, 邹毅, 陶传洲, 有机化学, 2011, 31, 2161.)
(c) Tian, J. J.; Guo, H. Y. Chin. J. Org. Chem. 2012, 32, 193 (in Chinese). (田金金, 郭红云, 有机化学, 2012, 32, 193.)
[2] Rao, A. R. R.; Rao, P. S. Eur. J. Med. Chem. 2009, 44, 1369.
[3] Parish, Jr., H. A.; Gilliom, R. D.; Purcell, W. P.; Browne, R. K.; Spirk, R. F.; White, H. D. J. Med. Chem. 1982, 25, 98.
[4] Liu, J. J.; Fu, Z.; Li, A. R.; Johnson, M.; Zhu, L.; Marcus, A.; Danao, J.; Sullivan, T.; Tonn, G.; Collins, T.; Medina, J. Bioorg. Med. Chem. Lett. 2009, 19: 5114.
[5] Peters, J.; Kuhne, H.; Dehmlow, H.; Grether, U.; Conte, A.; Hainzl, D.; Hertel, C.; Kratochwil, N. A.; Otteneder, M.; Narquizian, R.; Panousis, C. G.; Ricklin, F.; Rover, S. Bioorg. Med. Chem. Lett. 2010, 18, 5426.
[6] Suresh, T.; Kumar, R. N.; Mohan, P. S. Heterocycl. Commun. 2003, 9, 203.
[7] Yoneda, F.; Yamato, H.; Ono, M. J. Am. Chem. Soc. 1981, 103, 5943.
[8] Todd, E. M.; Zimmerman, S. C. Tetrahedron 2008, 64, 8558.
[9] (a) Gabor, B.; Rachel, L. B.; Fenniri, H. J. Heterocycl. Chem. 2009, 46, 79.
(b) El-Gazzar, A. R. B. A.; Hafez, H. N. Bioorg. Med. Chem. Lett. 2009, 19, 3392.
[10] Dabiri, M.; Arvin-Nezhad, H.; Resa, H.; Bazgir, A. Tetrahedron 2007, 63, 1770.
[11] Yang, L. P.; Shi, D. X.; Chen, S.; Chai, H. X.; Huang, D. F.; Zhang, Q.; Li, J. R. Green Chem. 2012, 14, 945.
[12] Graffner-Nordberg, M.; Kolmodin, K.; Åqvist, J.; Queener, S. F.; Hallberg, A. J. Med. Chem. 2001, 44, 2391.
[13] (a) Li, J. R.; Zhang, L. J.; Shi, D. X.; Li, Q.; Wang, D.; Wang, C. X.; Zhang, Q.; Zhang, L.; Fan, Y. Q. Synlett 2008, 233.
(b) Liu, X.; Shi, D. X.; Tang, J. H.; Zhang, Q.; Li, J. R. Chin. J. Org. Chem. 2011, 31, 1710 (in Chinese). (刘璇, 史大昕, 唐健红, 张奇, 李加荣, 有机化学, 2011, 31, 1710.)
(c) Liu, C.; Yu, Q. Y.; Tang, J. H.; Li, J. R. Chin. J. Org. Chem. 2012, 32, 532 (in Chinese). (刘长娥, 于琪瑶, 唐健红, 李加荣, 有机化学, 2012, 32, 193.)
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