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Synthesis of N , N ‐Disubstituted 1 ‐ Cyanocyclopropanecarboxamides
Author(s) -
Yamagata Kenji,
Okabe Fumi,
Tagawa Yoshinobu
Publication year - 2003
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200200516
Subject(s) - chemistry , sodium methoxide , yield (engineering) , ring (chemistry) , chloride , medicinal chemistry , sodium , stereochemistry , organic chemistry , methanol , materials science , metallurgy
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)