Efficient One-Pot Syntheses of 7-Alkyl-6H,7H-naphtho[1,2:5,6]pyrano-[3,2-c]chromen-6-ones by 1-Methyl-3-(2-(sulfooxy)ethyl)-1H-imidazol-3-ium Chloride
Yu Wan
Key Laboratory of Biotechnology on Medical Plant of Jiangsu Province, Xuzhou, 221116 People's Republic of China
Search for more papers by this authorChao Wang
School of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou, 221116 People's Republic of China
Search for more papers by this authorHai-ying Wang
School of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou, 221116 People's Republic of China
Key Laboratory of Green synthesis of functional material of Jiangsu Province, Xuzhou, 221116 People's Republic of China
Search for more papers by this authorLing-ling Zhao
School of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou, 221116 People's Republic of China
Key Laboratory of Green synthesis of functional material of Jiangsu Province, Xuzhou, 221116 People's Republic of China
Search for more papers by this authorXiao-xiao Zhang
School of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou, 221116 People's Republic of China
Search for more papers by this authorJing-jing Shi
School of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou, 221116 People's Republic of China
Search for more papers by this authorShu-ying Huang
School of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou, 221116 People's Republic of China
Search for more papers by this authorGui-Xiang Liu
School of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou, 221116 People's Republic of China
Search for more papers by this authorHui Wu
School of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou, 221116 People's Republic of China
Key Laboratory of Biotechnology on Medical Plant of Jiangsu Province, Xuzhou, 221116 People's Republic of China
Search for more papers by this authorYu Wan
Key Laboratory of Biotechnology on Medical Plant of Jiangsu Province, Xuzhou, 221116 People's Republic of China
Search for more papers by this authorChao Wang
School of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou, 221116 People's Republic of China
Search for more papers by this authorHai-ying Wang
School of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou, 221116 People's Republic of China
Key Laboratory of Green synthesis of functional material of Jiangsu Province, Xuzhou, 221116 People's Republic of China
Search for more papers by this authorLing-ling Zhao
School of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou, 221116 People's Republic of China
Key Laboratory of Green synthesis of functional material of Jiangsu Province, Xuzhou, 221116 People's Republic of China
Search for more papers by this authorXiao-xiao Zhang
School of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou, 221116 People's Republic of China
Search for more papers by this authorJing-jing Shi
School of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou, 221116 People's Republic of China
Search for more papers by this authorShu-ying Huang
School of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou, 221116 People's Republic of China
Search for more papers by this authorGui-Xiang Liu
School of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou, 221116 People's Republic of China
Search for more papers by this authorHui Wu
School of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou, 221116 People's Republic of China
Key Laboratory of Biotechnology on Medical Plant of Jiangsu Province, Xuzhou, 221116 People's Republic of China
Search for more papers by this authorAbstract
An efficient synthesis of 7-alkyl-6H,7H-naphtho-[10,20:5,6]pyrano[3,2-c]chromen-6-ones by three-component condensation reaction of β-naphthol, aromatic aldehydes, and 4-hydroxycoumarin catalyzed by 1-methyl-3-(2-(sulfooxy)ethyl)-1H-imidazol-3-ium chloride is reported in good to excellent yields and short reaction times.
REFERENCES AND NOTES
- 1 Jang, K. H.; Lee, B. H.; Choi, B. W.; Lee, H.-S.; Shin, J. J Nat Prod 2005, 68, 716.
- 2 Malquichagua Salazar, K. J.; Delgado Paredes, G. E.; Lluncor, L. R.; Young, M. C. M.; Kato, M. J. Phytochemistry 2005, 66, 573. 2005, 68, 716.
- 3 Burkhardt, G.; Becker, H.; Grubert, M. T. J.; Eicher, T. Phytochemistry 1992, 37, 1593.
- 4 Numata, A.; Kanbara, S.; Takahashi, C.; Fujiki, R.; Yoneda, M.; Usami, Y.; Fujita, E. Phytochemistry 1992, 31, 1209.
- 5 Kulkarni, M. M.; Nagasampagi, B. A.; Deshpande, S. G.; Sharma, R. N. Phytochemistry 2007, 26, 2969.
- 6 Isman, M. B.; Proksch, P. Phytochemistry 1985, 24, 1949.
- 7 Kitamura, R. O. S.; Romoff, P.; Young, M. C. M.; Kato, M. J.; Lago, J. H. G. Phytochemistry 2006, 67, 2398.
- 8 Shanthi, G.; Perumal, P. T.; Rao, U.; Sehgal, P. K. Indian J Chem Sec B 2007, 48B, 1319.
- 9 Foroumadi, A.; Dehghan, G.; Samzadeh-Kermani, A.; Arabsorkhi, F.; Sorkhi, M.; Shafiee, A.; Abdollahi, M. Asian J Chem 2007, 19, 1391.
- 10 Kumar, D.; Reddy, V. B.; Sharad, S.; Dube, U.; Kapur, S. Eur J Med Chem 2009, 44, 3805.
- 11 El-Saghier, A. M. M.; Naili, M. B.; Rammash, B. K.; Saleh, N. A.; Kreddan, K. M. Arkivoc 2007 (xvi), 83, 24.
- 12 Alizadeh, B. H.; Ostad, S. N.; Foroumadi, A.; Amini, M.; Dowlatabadi, R.; Navidpour, L.; Shafiee, A. Arkivoc 2008, (xiii), 45–56.
- 13 Gourdeau, H.; Leblond, L.; Hamelin, B.; Desputeau, C.; Dong, K.; Kianicka, I.; Custeau, D.; Boudreau, C.; Geerts, L.; Cai, S.-X.; Drewe, J.; Labrecque, D.; Kasibhatla, S.; Tseng, B. Mol Cancer Ther 2004, 3, 1375.
- 14 Reddy, P. N.; Reddy, Y. T.; Rao, M. K.; Rajitha, B. Heterocycl Commun 2003, 9, 647.
- 15 Cassidy, F.; Evans, J. M.; Hadley, M. S.; Haladij, A. H.; Leach, P. E.; Stemp, G. J Med Chem 1992, 35, 1623.
- 16 Wu, H.; Chen, X. M.; Wan, Y.; Xin, H. Q.; Xu, H. H.; Yue, C. H.; Pang, L. L.; Ma, R. Synthetic Communications 2009, 39, 37621.
- 17 Ma, W. W.; Wang, X.; Yan, F. L.; Wu, L. Q.; Wang, Y. L. Monatsh Chem 2011, 142, 163.
