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Studies on Heterocyclic Enaminonitriles, XVI. Reactions of 2-Benzamido-4,5-dihydro-3-thiophene- and -3-furancarbonitriles with Cyanomethylene Compounds

✍ Scribed by Yamagata, Kenji ;Hashimoto, Yoshichika ;Yamazaki, Motoyoshi

Publisher
John Wiley and Sons
Year
1994
Tongue
English
Weight
351 KB
Volume
1994
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

The reactions of 2‐benzamido‐4,5‐dihydro‐3‐thiophene‐ and ‐3‐furancarbonitriles (1 and 2) with ethyl or methyl cyanoacetate and malononitrile (2 equiv.) in the presence of sodium hydride (1 equiv.) in dimethyl sulfoxide at 140°C gave ethyl or methyl cyano[3‐cyano‐4,5‐dihydro‐2(3__H__)‐thienylidene‐ and ‐furanylidene]acetates (3a or 3b and 4a or 4b) and [3‐cyano‐4,5‐dihydro‐2(3__H__)‐thienylidene‐ and ‐furanylidene]propanedinitriles (3c and 4c). On the other hand, compound 2 reacted with malononitrile (2 equiv.) in the presence of sodium hydride (1 equiv.) in dimethylformamide at room temp. to give [(2‐amino‐4,5‐dihydro‐3‐furanyl)(benzamido)‐methylene]propanedinitrile (5). The same treatment of 2 with ethyl or methyl cyanoacetate followed by reaction with acetic anhydride gave ethyl or methyl 6‐acetoxy‐3‐benzamido‐2,4‐dicyano‐2‐hexenoate (6a or 6b). magnified image

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