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Synthesis of 2,3‐dihydro‐5 H ‐oxazolo[2,3‐ B ]quinazolin‐5‐ones
Author(s) -
Peet Norton P.,
Anzeveno Peter B.
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.5570160510
Subject(s) - chemistry , sodium iodide , yield (engineering) , iodide , ring (chemistry) , benzoic acid , methyl iodide , sulfuric acid , acetone , d 1 , medicinal chemistry , stereochemistry , organic chemistry , materials science , metallurgy , biochemistry , receptor
Iodide‐catalyzed ring expansion of 2‐[(1‐aziridinylcarbonyl)amino]benzoic acid methyl ester (2) gave 2,3‐dihydro‐5 H ‐oxazolo[2,3‐ b ]quinazolin‐5‐one (3) in quantitative yield. Treatment of the dimethyl analog of 2 (9) with sodium iodide in acetone gave a mixture of the 2,3‐dihydro‐2,2‐dimethyl‐ (10) and 2,3‐dihydro‐3,3‐dimethyl‐5 H ‐oxazolo[2,3‐ b ]quinazolin‐5‐ones (11). However, rearrangement of 9 with sulfuric acid produced only 10. Synthesis of 11 by another route for comparison is described, and the known syntheses of 2,3‐dihydro‐5 H ‐oxazolo[2,3‐ b ]quinazolin‐5‐ones are reviewed.