A Facile Synthesis of Oxoindenothiazine and Dioxospiro(indene‐2,4′‐thiazine) Derivatives from (Substituted ethylidene)hydrazinecarbothioamides |
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| Authors: | Alaa A Hassan Yusria R Ibrahim Essmat M El‐Sheref Mahmoud A A Ibrahim Stefan Bräse |
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| Institution: | 1. Chemistry Department, Faculty of Science, Minia University, El‐Minia, Egypt;2. School of Chemistry, University of Manchester, Manchester, United Kingdom;3. Institute of Organic Chemistry, Karlsruhe Institute of Technology, Karlsruhe, Germany |
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| Abstract: | (E)‐2‐2‐(1‐Substituted ethylidene)hydrazinyl]‐5‐oxo‐9b‐hydroxy‐5,9b‐dihydroindeno1,2‐d]1,3]‐thiazine‐4‐carbonitriles and (E)‐5‐oxo‐(E)‐(1‐substituted ethylidene)hydrazinyl]‐2,5‐dihydroindeno1,2‐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. |
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| Keywords: | (Substituted ethylidene)hydrazinecarbothioamides 2‐(1 3‐dioxo‐2 3‐dihydro‐1H‐inden‐2‐ylidene)propanedinitrile Oxoindenothiazines Dioxospiro(indene‐2 4′ ‐thiazines) |
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