A Facile Synthesis of Oxoindenothiazine and Dioxospiro(indene-2,4′-thiazine) Derivatives from (Substituted ethylidene)hydrazinecarbothioamides

(E)‐2‐[2‐(1‐Substituted ethylidene)hydrazinyl]‐5‐oxo‐9b‐hydroxy‐5,9b‐dihydroindeno[1,2‐d][1,3]‐thiazine‐4‐carbonitriles and (E)‐5‐oxo‐[(E)‐(1‐substituted ethylidene)hydrazinyl]‐2,5‐dihydroindeno[1,2‐d][1,3]thiazine‐4‐carbonitriles have been obtained from the reaction of 2‐(substituted ethylidene)hyd...

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Bibliographic Details
Published in:Journal of heterocyclic chemistry 2015-07, Vol.52 (4), p.1201-1207
Main Authors: Hassan, Alaa A., Ibrahim, Yusria R., El-Sheref, Essmat M., Ibrahim, Mahmoud A. A., Bräse, Stefan
Format: Article
Language:English
Subjects:
(Substituted ethylidene)hydrazinecarbothioamides
2‐(1,3‐dioxo‐2,3‐dihydro‐1H‐inden‐2‐ylidene)propanedinitrile
3-dihydro-1H-inden-2-ylidene)propanedinitrile
3-dioxo-2
4′-thiazines
Dioxospiro(indene-2
Dioxospiro(indene‐2,4′‐thiazines)
Oxoindenothiazines
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Summary:(E)‐2‐[2‐(1‐Substituted ethylidene)hydrazinyl]‐5‐oxo‐9b‐hydroxy‐5,9b‐dihydroindeno[1,2‐d][1,3]‐thiazine‐4‐carbonitriles and (E)‐5‐oxo‐[(E)‐(1‐substituted ethylidene)hydrazinyl]‐2,5‐dihydroindeno[1,2‐d][1,3]thiazine‐4‐carbonitriles have been obtained from the reaction of 2‐(substituted ethylidene)hydrazinecarbothioamides with 2‐(1,3‐dioxo‐2,3‐dihydro‐1H‐inden‐2‐ylidene)propanedinitrile (1) in ethyl acetate solution. However, (Z)‐6′‐amino‐1,3‐dioxo‐3′‐substituted‐2′‐[(E)‐(1‐phenylethylidene)hydrazono]‐1,2′,3,3′‐tetrahydrospiro(indene‐2,4′‐[1,3]thiazine)‐5′‐carbonitriles were observed during the reaction of N‐substituted‐2‐(1‐phenylethylidene)hydrazinecarbothioamides with (1). The structure assignment of products has been confirmed on the basis of 1H‐, 13C‐NMR, and mass spectrometry, as well as theoretical calculations.
ISSN:0022-152X
1943-5193
DOI:10.1002/jhet.2234