A Simple One-pot Synthesis of 3,5-Dicyano-1,2-dihydropyrid-2-ones in Aqueous Media
Qi-Ya ZHUANG
Key Laboratory of Biotechnology for Medicinal Plant, College of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou, Jiangsu 221116, China
Search for more papers by this authorJia-Ning XU
Key Laboratory of Biotechnology for Medicinal Plant, College of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou, Jiangsu 221116, China
Search for more papers by this authorRun-Hong JIA
Key Laboratory of Biotechnology for Medicinal Plant, College of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou, Jiangsu 221116, China
Search for more papers by this authorJun-Yong ZHANG
Key Laboratory of Biotechnology for Medicinal Plant, College of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou, Jiangsu 221116, China
Search for more papers by this authorChun-Mei LI
Key Laboratory of Biotechnology for Medicinal Plant, College of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou, Jiangsu 221116, China
Search for more papers by this authorDian-Xiang ZHOU
Key Laboratory of Biotechnology for Medicinal Plant, College of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou, Jiangsu 221116, China
Search for more papers by this authorQi-Ya ZHUANG
Key Laboratory of Biotechnology for Medicinal Plant, College of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou, Jiangsu 221116, China
Search for more papers by this authorJia-Ning XU
Key Laboratory of Biotechnology for Medicinal Plant, College of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou, Jiangsu 221116, China
Search for more papers by this authorRun-Hong JIA
Key Laboratory of Biotechnology for Medicinal Plant, College of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou, Jiangsu 221116, China
Search for more papers by this authorJun-Yong ZHANG
Key Laboratory of Biotechnology for Medicinal Plant, College of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou, Jiangsu 221116, China
Search for more papers by this authorChun-Mei LI
Key Laboratory of Biotechnology for Medicinal Plant, College of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou, Jiangsu 221116, China
Search for more papers by this authorDian-Xiang ZHOU
Key Laboratory of Biotechnology for Medicinal Plant, College of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou, Jiangsu 221116, China
Search for more papers by this authorAbstract
A simple and clean synthesis of 3,5-dicyano-1,2-dihydropyrid-2-ones by a one-pot three-component reaction of malononitrile, aromatic aldehydes and 2-cyanoacetamide or 2-cyanothioacetamide has been achieved in an aqueous solution with potassium carbonate as a base under microwave irradiation without a phase transfer reagent. This protocol has the advantages of short reaction time (5–8 min) and convenient work-up.
REFERENCES
- 1a Li, C. J.; Chen, L.. Chem. Soc. Rev., 2006, 35, 68.
- 1b Ju, Y. H.; Varma, R. S.. Chem. Rev., 2005, 79, 2409.
- 2a Akiya, N.; Savage, P. E.. Chem. Rev., 2002, ,102, 2725.
- 2b Breslow, R.. Acc. Chem. Res., 1991, 24, 159.
- 2c Breslow, R.; Rideout, D. C.. J. Am. Chem. Soc., 1980, 102, 7816.
- 2d Darr, J. A.; Poliakoff, M.. Chem. Rev., 1999, 99, 495.
- 2e Clifford, A. A.; Rayer, C. M.. Tetrahedron Lett., 2001, 42, 323.
- 3a Thadani, A. N.; Batey, R. A.. Org. Lett., 2002, 4, 3827.
- 3b Thadani, A. N.; Batey, R. A.. Tetrahedron Lett., 2003, 44, 8051.
- 4a Tu, S. J.; Miao, C. B.; Fang, F.; Feng, Y. J.; Li, T. J.; Zhuang, Q. Y.; Zhang, X. J.; Zhu, S. L.; Shi, D. Q.. Bioorg. Med. Chem. Lett., 2004, 14, 1533.
- 4b Tu, S. J.; Miao, C. B.; Gao, Y.; Fang, F.; Zhuang, Q. Y.; Feng, Y. J.; Shi, D. Q.. Synlett, 2004, 255.
- 4c Strübing, D.; Neumann, H.; Wangelin, A. J. von; Klaus, S.; Hübner, S.; Beller, M.. Tetrahedron, 2006, 62, 10962.
- 4d Bremner, W. S.; Organ, M. G.. J. Comb. Chem., 2007, 9, 14.
- 5 Li, Q.; Mitscher, L. A.; Shen, L. L.. Med. Res. Rev., 2000, 20, 231.
- 6 Cox, R. J.; O'Hagan, D.. J. Chem. Soc., Perkin Trans. 1, 1991, 2537.
- 7 Nagarajan, M.; Xiao, X. S.; Antony, S.; Kohlhagen, G.; Pommier, Y.; Cushman, M.. J. Med. Chem., 2003, 46, 5712.
- 8 Hasvold, L. A.; Wang, W. B.; Gwaltney, S. L.; Rockway, T. W.; Nelson, L. T. J.; Mantei, R. A.; Fakhoury, S. A.; Sullivan, G. M.; Li, Q.; Lin, N. H.; Wang, L.; Zhang, H. Y.; Cohen, J.; Gu, W. Z.; Marsh, K.; Bauch, J.; Rosenberg, S.; Sham, H. L.. Bioorg. Med. Chem. Lett., 2003, 13, 4001.
- 9a Deshang, P.; Cipollina, J. A.; Lowmoster, N. K.. J. Org. Chem., 1988, 53, 1356.
- 9b Ryabukhin, S. V.; Plaskon, A. S.; Volochnyuk, D. M.; Tolmachev, A. A.. Synlett, 2004, 2287.
- 10 Kozikowski, A.; Campiani, G.; Sun, L. Q.; Wang, S.; Saxena, A.; Doctor, B.. J. Am. Chem. Soc., 1996, 118, 11357.
- 11 Beckman, R. K.; Potenza, J. C.; Enholm, E. J.. J. Org. Chem., 1987, 52, 469.
- 12a Comins, D. L.; Hong, H.; Saha, J. K.; Gao, J. H.. J. Org. Chem., 1994, 59, 5120.
- 12b Comins, D. L.; Hong, H.; Gao, J. H.. Tetrahedron Lett., 1994, 35, 5331.
- 12c Bernstein, P. R.; Gomes, B. C.; Kosmider, B. J.; Vacek, E. P.; Williams, J. C.. J. Med. Chem., 1995, 38, 212.
- 12d Kozikowski, A. P.; Campiani, G.; Sun, L. Q.; Wang, S.; Saxena, A.; Doctor, B. P.. J. Am. Chem. Soc., 1996, 118, 11357.
- 12e Williams, D. R.; Lowder, P. D.; Gu, Y. G.. Tetrahedron Lett., 1997, 38, 327.
- 13 Gante, J.; Lust, S.. US 3629270, Chem. Abstr. 1970, 73, 120510.
- 14a Kambe, S.; Saito, K.. Synthesis, 1981, 531.
- 14b Matrosova, S. V.; Zav'yalova, V. K.; Litvinov, V. P.; Sharanin, Y. A.. Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1991, 1643.
- 14c Elnagdi, M. H.; Elghandour, A. H. H.; Ibrahim, M. K. A.; Hafiz, I. S. A. Z.. Naturforsch., 1992, 47b, 572.
- 14d Sharanin, Y. A.; Shestopalov, A. M.; Nesterov, V. N.; Melenchuk, S. N.; Promonenkov, V. K.; Shklover, V. E.; Struchkov, Y. T.; Litvinov, V. P.. Zh. Org. Khim., 1989, 25, 1323.
- 14e Dyachenko, V. D.; Krivokolysko, S. G.; Nesterov, V. N.; Litvinov, V. P.. Chem. Heterocycl. Compd., 1997, 33, 1430.
- 14f Dyachenko, V. D.; Litvinov, V. P.. Chem. Heterocycl. Compd., 1998, 34, 188.
- 14g Dyachenko, V. D.; Litvinov, V. P.. Russ. J. Org. Chem., 1998, 34, 557.
- 14h Quintela, J. M.; Peinador, C.; Veiga, M. C.; Botana, L. M.; Alfonso, A.; Riguera, R.. Eur. J. Med. Chem., 1998, 33, 887.
- 14i Attia, A. M. E.; Ismail, A. E. A. A.. Tetrahedron, 2003, 59, 1749.
- 14j Soto, J. L.; Seoane, C.; Zamorano, P.; Cuadrado, F. J.. Synthesis, 1981, 529.
- 14k Dyachenko, V. D.; Krivokolysko, S. G.; Sharanin, Y. A.; Litvinov, V. P.. Russ. J. Org. Chem., 1997, 33, 1014.
- 15a Tu, S. J.; Jia, R. H.; Jiang, B.; Zhang, J. Y.; Zhang, Y.; Yao, C. S.; Ji, S. J.. Tetrahedron, 2007, 63, 381.
- 15b Tu, S. J.; Jiang, B.; Zhang, J. Y.; Jia, R. H.; Zhang, Y.; Yao, C. S.. Org. Biomol. Chem., 2006, 4, 3980.
- 15c Tu, S. J.; Zhang, Y.; Zhang, J. Y.; Jiang, B.; Jia, R. H.; Zhang, J. P.; Ji, S. J.. Synlett, 2006, 2785.
- 16 Evdokimov, N. M.; Magedov, I. V.; Kireev, A. S.; Kornienko, A.. Org. Lett., 2006, 8, 899.
