Heterocyclic compounds from 3,3‐dimercapto‐1 ‐aryl‐2‐propen‐1‐ones. Note 2. Condensation with o‐aminothophenol and o‐aminophenol
- 1 February 1975
- journal article
- research article
- Published by Wiley in Journal of Heterocyclic Chemistry
- Vol. 12 (1) , 139-142
- https://doi.org/10.1002/jhet.5570120124
Abstract
The condensation of 3,3‐dimercapto‐1‐phenyl‐2‐propen‐1‐one with o‐aminothiophenol and o‐aminophenol in hot xylene gave 2‐phenacylbenzothiazole (3) and 2‐phenacylbenzoxazole (5). When the reaction with o‐aminophenol was carried out in hot benzene, 2‐beuzoylthioacctamidophenol (4) was obtained, which, heated in hot xylene gave 5. Ethyl benzoylacetale by reaction with o‐aminothiophenol gave 3, whereas by reaction with o‐aminophenol gave no heterocyclic compound. However, we were able to isolate 2‐benzoylacetamidophenol (6), ethyl β‐phenyl‐β‐(o‐hydroxy)phenyliminopropionate (7), and 2‐[β‐(o‐hydroxy)anilino] cinnamoylamidophenol (8). Ir and nmr spectra of synthesized compounds point out the existence of tautomers.Keywords
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