Abstract
A new series of 4-alkyl(aryl)-4-tetramethylenesulfoximide-1,1,1-trifluoroalk-3-en-2-ones has been prepared from the O,N-exchange reactions of 4-alkyl(aryl)-4-alkoxy-1,1,1-trifluoroalk-3-en-2-ones with the cyclic S,Stetramethylenesulfoximide in absence of solvent, in good yields. Subsequently, the easy preparation of a new series of a fused heterocyclic system of 3-aryl-5-trifluoromethyl-7,8-dihydro-6H-thieno[2,1-f][1,2]thiazine 1-oxide derivatives (60- 85% yields) from intramolecular cyclization reactions of sulfoximide enones employing potassium t-butoxide in diethyl ether at reflux is also reported.
Keywords: Sulfoximides, trifluoromethyl ketones, 1,2-thiazines, enaminoketones
Letters in Organic Chemistry
Title: An Easy Approach to the Synthesis of New Fused 3-Aryl-5- trifluoromethyl-7,8-dihydro-6H-thieno [2,1-f] [1,2] thiazine 1-Oxide System
Volume: 6 Issue: 2
Author(s): Helio G. Bonacorso, Renata P. Vezzosi, Roberta L. Drekener, Nilo Zanatta and Marcos A. P. Martins
Affiliation:
Keywords: Sulfoximides, trifluoromethyl ketones, 1,2-thiazines, enaminoketones
Abstract: A new series of 4-alkyl(aryl)-4-tetramethylenesulfoximide-1,1,1-trifluoroalk-3-en-2-ones has been prepared from the O,N-exchange reactions of 4-alkyl(aryl)-4-alkoxy-1,1,1-trifluoroalk-3-en-2-ones with the cyclic S,Stetramethylenesulfoximide in absence of solvent, in good yields. Subsequently, the easy preparation of a new series of a fused heterocyclic system of 3-aryl-5-trifluoromethyl-7,8-dihydro-6H-thieno[2,1-f][1,2]thiazine 1-oxide derivatives (60- 85% yields) from intramolecular cyclization reactions of sulfoximide enones employing potassium t-butoxide in diethyl ether at reflux is also reported.
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Bonacorso G. Helio, Vezzosi P. Renata, Drekener L. Roberta, Zanatta Nilo and Martins A. P. Marcos, An Easy Approach to the Synthesis of New Fused 3-Aryl-5- trifluoromethyl-7,8-dihydro-6H-thieno [2,1-f] [1,2] thiazine 1-Oxide System, Letters in Organic Chemistry 2009; 6 (2) . https://dx.doi.org/10.2174/157017809787582726
DOI https://dx.doi.org/10.2174/157017809787582726 |
Print ISSN 1570-1786 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-6255 |
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