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Synthesis of 3‐arylamino‐4(3 H )quinazolinone derivatives from 1‐acetyl‐ or 1‐ethoxycarbonylmethylene‐2‐arylhydrazines
Author(s) -
Trimarco Pasqualina,
Lastrucci Cristina
Publication year - 1976
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.5570130447
Subject(s) - chemistry , quinazolinone , decarboxylation , acetic anhydride , hydrolysis , ring (chemistry) , medicinal chemistry , organic chemistry , catalysis
By reacting 1‐acetyl‐ or 1‐ethoxycarbonylehloromethylene‐2‐arylhydrazines ( 2a‐c ) with anthranilic acids (1a‐b) the corresponding C ‐acetyl‐ or C ‐ethoxyearbonylcarbohydrazonamide derivatives (3a‐d) were obtained. Ring closure of the carbohydrazonamides with acetic anhydride afforded 2‐carboethoxy‐ or 2‐acetyl‐3‐arylamino‐4(3 H )quinazolinones ( 4a‐d ). The ester derivatives undergo basic hydrolysis with decarboxylation to 3‐arylamino‐4(3 H )quinazolinones ( 5a‐b ).