Chinese Journal of Organic Chemistry >
Reactions of Acetophenonyl Pyridinium Salts with Alcohols
Received date: 2014-06-23
Revised date: 2014-08-08
Online published: 2014-08-28
Supported by
Project supported by the National Natural Science Foundation of China (No. 20872031) and the Key Laboratory for the Synthesis and Application of Organic Functional Molecules, Ministry of Education.
Acetophenonyl pyridinium salts are versatile reagents in organic reactions, but the reactivities of their carbonyls were seldomly studied. It was found that the reactions of the carbonyls with alcohols occurred when acetophenonyl pyridinium salts were treated with alcohols (or phenol) in the presence of a base giving rise to benzoates, and the departure of pyridyl with the α-carbon atom was involved. High yields (80%~98%) were achieved when they reacted with alcohols, however a yield of 48% were obtained when phenol was used instead of alcohols.
Key words: acetophenonyl pyridinium salt; alcohol; derivative of benzoate
She Chuan , Zhou Jie , Chen Hui , Liu Xufeng , Zhang Wanxuan . Reactions of Acetophenonyl Pyridinium Salts with Alcohols[J]. Chinese Journal of Organic Chemistry, 2014 , 34(12) : 2551 -2553 . DOI: 10.6023/cjoc201406036
[1] (a) Kröhnke, F. Angew. Chem., Int. Ed. 1963, 2, 225. (b) Wu, P.; Wang, Q.-F.; Cai, X.-M.; Yan, C.-G. Chin. J. Org. Chem. 2008, 28, 1899 (in Chinese). (吴萍, 王琦芳, 蔡习美, 颜朝国, 有机化学, 2008, 28, 1899.) (c) Osyanin, V. A.; Osipov, D. V.; Klimochkin, Y. N. J. Org. Chem. 2013, 78, 5505.
[2] Zhao, L.-X.; Moon, Y.-S.; Basnet, A.; Kim, E.-K.; Jahng, Y.; Park, J. G.; Jeong, T. C.; Cho, W.-J.; Choi, S.-U.; Lee, C. O.; Lee, S.-Y.; Lee, C.-S.; Lee, E.-S. Bioorg. Med. Chem. Lett. 2004, 14, 1333.
[3] (a) Yang, Y.; Gao, M.; Zhang, D.-X.; Wu, L.-M.; Shu, W.-M.; Wu, A.-X. Tetrahedron 2012, 68, 7338. (b) Shang, Y.; Zhang, M.; Yu, S.; Ju, K.; Wang, C.; He, X. Tetrahedron Lett. 2009, 50, 6981.
[4] Wu, P.; Cai, X.-M.; Wang, Q.-F.; Yan, C.-G. Synth. Commun. 2007, 37, 223.
[5] (a) King, L. C. J. Am. Chem. Soc. 1944, 66, 894. (b) Babcock, S. H.; Nakamura, J. F. I.; Fuson, R. C. J. Am. Chem. Soc. 1932, 54, 4407.
[6] Phillips, W. G.; Ratts, K. W. J. Org. Chem. 1970, 36, 3144.
[7] Weng, S.-S.; Ke, C.-S.; Chen, F.-K.; Lyu, Y.-F.; Lin, G.-Y. Tetrahedron 2011, 67, 1640.
[8] Bao, Y.-S.; Chen, C.-Y.; Huang, Z.-Z. J. Org. Chem. 2012, 77, 8344.
[9] Tian, J.; Gao, W.-C.; Zhou, D.-M.; Zhang, C. Org. Lett. 2012, 14, 3020.
[10] (a) Ram, R. N.; Soni, V. K.; Gupta, D. K. Tetrahedron 2012, 68, 9068. (b) Ding, J.-C.; Wu, S.-W.; Cai, C.-H. Chin. J. Synth. Chem. 2000, 8, 184 (in Chinese). (丁金昌, 吴声文, 蔡昌慧, 合成化学, 2000, 8, 184.)
[11] Iwasaki, T.; Maegawa, Y.; Hayashi, Y.; Ohshima, T.; Mashima, K. J. Org. Chem. 2008, 73, 5147.
[12] Liu, Q.; Li, G.; He J.; Liu, J.; Li, P.; Lei, A. Angew. Chem., Int. Ed. 2010, 49, 3371.
[13] Won, J.-E.; Kim, H.-K.; Kim, J.-J.; Yim, H.-S.; Kim, M.-J.; Kang, S.-B.; Chung, H.-A.; Lee, S.-G.; Yoon, Y.-J. Tetrahedron 2007, 63, 12720.
[14] Bamoharram, F. F.; Heravi, M. M.; Roshani, M.; Jahangir, M.; Gharib, A. Appl. Catal. A: Gen. 2006, 302, 42.
/
| 〈 |
|
〉 |