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A Facile Synthesis of Oxoindenothiazine and Dioxospiro(indene‐2,4′‐thiazine) Derivatives from (Substituted ethylidene)hydrazinecarbothioamides
Author(s) -
Hassan Alaa A.,
Ibrahim Yusria R.,
ElSheref Essmat M.,
Ibrahim Mahmoud A. A.,
Bräse Stefan
Publication year - 2015
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.2234
Subject(s) - chemistry , thiazine , indene , medicinal chemistry , mass spectrometry , chromatography
( 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‐1 H ‐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 1 H‐, 13 C‐NMR, and mass spectrometry , as well as theoretical calculations.