Chemistry of Heterocyclic Compounds p. 1293 - 1297 (1983)
Update date:2022-08-02
Topics:
Orlov, V. D.
Kolos, N. N.
Ruzhitskaya, N. N.
2,4-Diaryl-2,3-dihydrobenzo<1,4>thiazepines are obtained in a single stage from chalcones and ortho-aminothiophenol in the presence of triethylamine.The nature of the electronic transitions in their UV absorption spectra is discussed with the use of quantum-chemical methods.It was shown that the seven-membered ring does not invert in the range of temperatures between -80 and +140 deg C and is in the boat form.The main initial event in the fragmentation of the molecules of the obtained compounds under electron impact is the formation of benzothiazole-containing radicalions.In an acidic medium 2,4-diphenyl-2,3-dihydrobenzo<1,4>thiazepine is hydrolyzed to 3-(2-aminophenylthio)-1,3-diphenyl-1-propanone, and in its reaction with 2,4-dinitrophenylhydrazine chalcone hydrazone and o-aminothiophenol are formed.
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