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Acetylenic chemistry: Part 13 . Synthesis of oxazoles and oxazoloquinazolines from o ‐amino‐ N ‐(1,1 ‐disubstituted‐propynyl)benzamide
Author(s) -
Reisch J.,
Usifoh C. O.,
Oluwadiya J. O.
Publication year - 1989
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.5570260546
Subject(s) - chemistry , propynyl , triphosgene , benzamide , potassium hydroxide , pyridine , methylene , medicinal chemistry , stereochemistry , organic chemistry , phosgene
Conversion of isatoic anhydride to o ‐amino‐ N (1,1‐disubstituted‐propynyl)benzamides 3a‐c followed by reflux in ethanolic potassium hydroxide gave 2‐( o ‐aminophenyl)‐4,4‐disubstituted‐5‐methylene‐4 H ‐oxazoles 4a‐c . The treatment of same 3a‐c with triphosgene in pyridine with subsequent reflux gave 4a‐c and 2‐methylene‐3,3‐disubstituted‐oxazolo[2,3‐ b ]quinazolin‐5(3 H )‐ones 5a‐c.