Premium
Novel heterocycles. 5 . Lactone fused quinazolines
Author(s) -
Coppola Gary M.,
Shapiro Michael J.
Publication year - 1980
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.5570170602
Subject(s) - chemistry , lactone , sodium methoxide , hydrolysis , quinazoline , sodium iodide , iodide , organic chemistry , methanol
Quinazoline fused lactones were synthesized. The six‐membered lactone 7 was prepared by the interaction of ethyl pyruvate with hydroxyethylanthranilamide 11 , followed by hydrolysis and cyclization using 1‐methyl‐2‐choropyridinium iodide. The corresponding seven‐membered lactone 10 was prepared by reaction of 11 with ethyl propiolate, followed by hydrolysis and cyclization as above. Quinazolines possessing functionalities capable of forming either a six‐ or seven‐membered lactone were cyclized in xylene in the presence of sodium methoxide. Only the six‐membered lactone 14 formed.