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Heterocycles from substituted amides. VI . A new carbostyril synthesis from alpha ‐substituted acetamides and the vilsmeier reagent
Author(s) -
Chupp John P.,
Metz Suzanne
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.5570160115
Subject(s) - chemistry , reagent , acetanilide , ring (chemistry) , electrophile , scope (computer science) , combinatorial chemistry , medicinal chemistry , organic chemistry , catalysis , computer science , programming language
Abstract Reaction of tertiary α‐substituted acetanilides with Vilsmeier reagent has been found to give 1,3‐disubstituted‐carbostyrils, 1. α‐Chloro‐ N ‐(1‐cyclohexen‐1‐yl) acetamides are similarly converted to tetrahydro carbostyrils 2 and 3. The method appears useful for the preparation of a variety of 1,3‐substituted 2(1 H ) quinolinones. The scope and mechanism of the reaction has been investigated, with evidence presented to indicate the ring‐closure proceeds via electrophilic attack of Vilsmeier reagent on intermediate chlorenamine.