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Studies on Heterocyclic Enaminonitriles, XII. Reactions of 4,5-Dihydro-2-morpholino- (and -2-pyrrolidino)-3-furancarbonitriles with Dichlorocarbene

✍ Scribed by Yamagata, Kenji ;Takaki, Mikiko ;Yamazaki, Motoyoshi


Publisher
John Wiley and Sons
Year
1992
Tongue
English
Weight
415 KB
Volume
1992
Category
Article
ISSN
0947-3440

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✦ Synopsis


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.


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