Synthesis of N,N-Disubstituted 1-Cyanocyclopropanecarboxamides

2‐(Disubstituted amino)‐4,5‐dihydro‐3‐furancarbonitriles 1a−i reacted with acetyl chloride to yield the corresponding ring‐opening products 2a−i. The cyclization of compounds 2a−f with bases gave the corresponding N,N‐disubstituted 1‐cyanocyclopropanecarboxamides 3a−c and (E)‐1‐cyano‐2‐phenylcyclopr...

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Bibliographic Details
Published in:European journal of organic chemistry 2003-07, Vol.2003 (13), p.2383-2387
Main Authors: Yamagata, Kenji, Okabe, Fumi, Tagawa, Yoshinobu
Format: Article
Language:English
Subjects:
Acetyl chloride
Cyclization
Cyclopropanes
Furans
Ring opening
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Summary:2‐(Disubstituted amino)‐4,5‐dihydro‐3‐furancarbonitriles 1a−i reacted with acetyl chloride to yield the corresponding ring‐opening products 2a−i. The cyclization of compounds 2a−f with bases gave the corresponding N,N‐disubstituted 1‐cyanocyclopropanecarboxamides 3a−c and (E)‐1‐cyano‐2‐phenylcyclopropanecarboxamides 3d−f. The same compounds 3d−f were also obtained by treatment of compounds 2g−i with sodium methoxide. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200200516