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The preparation of 4‐oxo‐ N ‐aryl‐4 H ‐1‐benzopyran‐2‐acetamides by the condensation/cyclization of trilithiated acetoacetanilides with lithiated methyl salicylates
Author(s) -
Hurst Douglas R.,
French Kristen L.,
Angel April J.,
Williams Angela R.,
Rampey Mary E.,
Guion Tina S.,
Chan Kam W.,
Kassis Camille M.,
Martinez Shan L. Studer,
Beam Charles F.
Publication year - 1998
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.5570350622
Subject(s) - lithium diisopropylamide , chemistry , aryl , condensation , benzopyran , lithium (medication) , organic chemistry , medicinal chemistry , ion , deprotonation , thermodynamics , medicine , alkyl , physics , endocrinology
Several acetoacetanilides were trilithiated in excess lithium diisopropylamide, and the resulting polylithiated intermediates were regioselectively condensed with lithiated methyl salicylates followed by acid cyclization to substituted 4‐oxo‐ N ‐aryl‐4 H ‐1‐benzopyran‐2‐acetamides (benzopyranone‐2‐acetamides).