A Facile Synthesis of Oxoindenothiazine and Dioxospiro(indene‐2, 4′‐thiazine) Derivatives from (Substituted ethylidene)hydrazinecarbothioamides. (24th June 2014)

• Record Type: Journal Article
• Authors: Hassan, Alaa A.; Ibrahim, Yusria R.; El‐Sheref, Essmat M.; Ibrahim, Mahmoud A. A.; Bräse, Stefan
• Is Part Of: Journal of heterocyclic chemistry. Volume 52:Number 4(2015)
• Page Start: 1201
• Page End: 1207
• Publication Date: 2014-06-24
• Subjects: Heterocyclic compounds -- Periodicals; 547.59
• DOI: 10.1002/jhet.2234
• Languages: English
• ISSNs: 0022-152X

Abstract

<abstract abstract-type="main"> <title> <x xml:space="preserve">Abstract</x> </title> <p>(<italic>E</italic>)‐2‐[2‐(1‐Substituted ethylidene)hydrazinyl]‐5‐oxo‐9b‐hydroxy‐5, 9b‐dihydroindeno[1, 2‐<italic>d</italic>][1, 3]‐thiazine‐4‐carbonitriles and (<italic>E</italic>)‐5‐oxo‐[(<italic>E</italic>)‐(1‐substituted ethylidene)hydrazinyl]‐2, 5‐dihydroindeno[1, 2‐<italic>d</italic>][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<italic>H</italic>‐inden‐2‐ylidene)propanedinitrile (<bold>1</bold>) in ethyl acetate solution. However, (<italic>Z</italic>)‐6′‐amino‐1, 3‐dioxo‐3′‐substituted‐2′‐[(<italic>E</italic>)‐(1‐phenylethylidene)hydrazono]‐1, 2′, 3, 3′‐tetrahydrospiro(indene‐2, 4′‐[1, 3]thiazine)‐5′‐carbonitriles were observed during the reaction of <italic>N</italic>‐substituted‐2‐(1‐phenylethylidene)hydrazinecarbothioamides with (<bold>1</bold>). The structure assignment of products has been confirmed on the basis of ¹H‐, ¹³C‐NMR, and <named-content content-type="chemicalTechnology" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">mass spectrometry</named-content>, as well as theoretical calculations.</p> </abstract>