K. Yamagata, M. Takaki, M. Yamazaki
Nov 20, 1992
Citations
0
Influential Citations
7
Citations
Journal
European Journal of Organic Chemistry
Abstract
The reaction of 4,5-dihydro-2-morpholino- (and -2-pyrrolidino)-3-furancarbonitriles 1a, c, d and 2a, c, d with dichlorocarbene gave 4-(2,4-pentadienoyl)morpholines 3a, c, d and 1-(2,4-pentadienoyl)pyrrolidines 4a, c, d. Similarly, the reaction of 4,5-dihydro-5-methyl-2-morpholino- (and -2-pyrrolidino)-3-furancarbonitrile 1b and 2b afforded the corresponding 4-(2-chloro-3-cyano-2,4-hexadienoyl)morpholine (3b) and 1-(2-chloro-3-cyano-2,4-hexadienoyl)pyrrolidine (4b). The starting compounds 1a–d and 2a–d were synthesized by the reaction of 2-amino-4,5-dihydro-3-furancarbonitriles with morpholine (and pyrrolidine) in the presence of trimethylamine hydrochloride in dioxane.