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Synthesis of α-alkylidene-γ-butyrolactones via Ring-cleavage/recyclization of 2-Amino-4,5-dihydro-3-furancarboxamides

✍ Scribed by Fumi Okabe; Yoshinobu Tagawa; Kenji Yamagata

Publisher
Journal of Heterocyclic Chemistry
Year
2004
Tongue
English
Weight
151 KB
Volume
41
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

The reactions of 2‐amino‐4,5‐dihydro‐3‐furancarboxarnides 1a,b with cyanomethylene compounds (such as alkyl cyanoacetates and malononitrile) gave the corresponding ring‐opened products 2a‐f. Compounds 2a‐d reacted with methanesulfonic acid to give the corresponding α‐alkylidene‐γ‐butyrolactones 3a‐d. On the other hand, treatment of 2e,f with methanesulfonic acid yielded 3‐pyridinecarbonitrile derivatives 4a,b.

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