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Reaction of ketenes with N,N ‐disubstituted α‐aminomethyleneketones VIII. Synthesis of N,N ‐disubstituted 4‐amino‐3‐chloro‐6‐phenyl‐2 H ‐pyran‐2‐ones
Author(s) -
Bargagna Alberto,
Sche Pietro,
Evangelisti Filippo
Publication year - 1979
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570160119
Subject(s) - chemistry , pyran , medicinal chemistry , stereochemistry , cycloaddition , organic chemistry , catalysis
Abstract The dipolar 1,4‐cycloaddition of dichloroketene to N,N ‐disubstituted 3‐amino‐1‐phenyl‐2‐propene‐1‐onesled directly to N,N ‐disubstituted 4‐amino‐3‐chloro‐6‐phenyl‐2 H ‐pyran‐2‐ones only in the case of an usual aliphatic N,N ‐disubstitution. In the case of partial or full aromatic N ‐substitution, N,N ‐disubstituted 4‐amino‐3,3‐dichloro‐3,4‐dihydro‐6‐phenyl‐2 H ‐pyran‐2‐ones were instead obtained, which were dehydrochlorinated with DBN to the corresponding 4‐amino‐3‐chloro‐6‐phenyl‐2 H ‐pyran‐2‐ones.