340020-38-4Relevant articles and documents
Unexpected ring size effect of the annulation reaction of heterocyclic secondary enamines with dicarboxylic acid dichlorides
Cheng, Ying,Yang, Hai-Bo,Wang, Mei-Xiang,Williams, David J
, p. 2821 - 2829 (2002)
Heterocyclic enamines are versatile ambident nucleophilic reagents able to react with both aliphatic and aromatic dicarboxylic acid dichlorides in diverse manners. The reaction outcome was strongly dependent upon the heterocyclic structure of the enamines
Annulation of heterocyclic secondary enamines with dicarboxylic acid dichlorides, an unexpected ring size effect
Cheng, Ying,Yang, Hai-Bo,Huang, Zhi-Tang,Wang, Mei-Xiang
, p. 1757 - 1759 (2001)
Under very mild conditions heterocyclic secondary enamines react efficiently with malonyl chloride to produce hydroxylated 2-pyridinone-fused heterocycles. The reactions of enamines with oxalyl chloride, however, afford varied products depending upon the heterocyclic structure of the enamine. Whilst a C-acylated enamine and a lactam-fused heterocycle were obtained from the reaction of the five- and seven-membered heterocyclic enamines, respectively, the six-membered heterocyclic enamine gave 2-oxo-5,6,7,8-tetrahydro-2H-pyrido[3,2-b]pyran. The reaction mechanisms are discussed.
