SmCl3-catalyzed C-acylation of 1, 3-dicarbonyl compounds and malononitrile
Q Shen, W Huang, J Wang, X Zhou
Index: Shen, Quansheng; Huang, Wen; Wang, Jialiang; Zhou, Xigeng Organic Letters, 2007 , vol. 9, # 22 p. 4491 - 4494
Full Text: HTML
Citation Number: 28
Abstract
A recyclable, convenient, and efficient catalytic system for C-acylation of 1, 3-dicarbonyl compounds and malononitrile with acid chlorides has been developed, giving moderate to excellent yields under mild conditions. This is the first catalytic example of such reactions. In addition, by applying this protocol as the key step, 3, 5-disubstituted-1 H-pyrazole-4- carboxylate can easily be synthesized in high yields in a one-pot procedure.
Related Articles:
[Okimoto, Mitsuhiro; Chiba, Toshiro Journal of Organic Chemistry, 1993 , vol. 58, # 23 p. 6194 - 6197]
[Kunieda, Takehisa; Higuchi, Tsunehiko; Abe, Yoshihiro; Hirobe, Masaaki Tetrahedron, 1983 , vol. 39, # 20 p. 3253 - 3260]
Expedient acylations of primary and secondary alkyl cyanides to α-substituted β-ketonitriles
[Kayaleh, Nadim E.; Gupta, Ramesh C.; Johnson, Francis Journal of Organic Chemistry, 2000 , vol. 65, # 15 p. 4515 - 4522]
[Shioiri,T.; Hamada,Y. Journal of Organic Chemistry, 1978 , vol. 43, p. 3631 - 3632]