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Synthesis of 2,7‐disubstituted‐5,6‐dimethylpyrrolo‐[2,3‐ d ]‐1,3‐oxazin‐4‐ones as antifungal agents
Author(s) -
Player Mark R.,
Sowell J. Walter,
Williams Glenn R.,
Cowley Gerald T.
Publication year - 1994
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.5570310135
Subject(s) - chemistry , allylamine , substituent , acetic anhydride , antifungal , lactam , stereochemistry , organic chemistry , microbiology and biotechnology , polyelectrolyte , catalysis , biology , polymer
A series of novel 5,6‐dimethylpyrrolo[2,3‐ d ]‐1,3‐oxazin‐4‐ones were synthesized from 2‐amino‐3‐ tert ‐butoxy‐carbonyl‐4,5‐dimethylpyrroles. Two methods were used, cyclodehydration of 2‐acylamino‐3‐carboxypyrroles with acetic anhydride and direct conversion of the 5,6‐dimethylpyrrolo[2,3‐ d ]‐1,3‐oxazin‐2,4‐diones to the title compounds with an anhydride directly providing the 2 substituent. Molecular modeling techniques revealed that these pyrrolo[2,3‐ d ]oxazinones were rigid analogues of the allylamine antifungals. The compounds were tested for in vitro activity against Tricophyton and Scopulariopsis sp.