Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5223368 | Tetrahedron | 2009 | 8 Pages |
Abstract
(1E,3Z)-1-Aryl-4-methanesulfonyl-2-nitro-1,3-butadienes (8), derived from the initial ring-opening of 3-nitrothiophene (5), have been found to undergo a facile base-induced cyclization leading to thiopyran S,S-dioxides (9), thus furnishing a further example of effective ring-enlargement from 5- to 6-membered sulfur heterocycles. Compounds 9 are obtained as single racemic mixtures in satisfactory yields; they still contain a nitrovinylic moiety, which can be exploited for further modifications targeted to new derivatives endowed with either synthetic or pharmacological potentialities e.g., in the field of L-type Ca2+-channel blockers.
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Organic Chemistry
Authors
Lara Bianchi, Massimo Maccagno, Giovanni Petrillo, Egon Rizzato, Fernando Sancassan, Elda Severi, Domenico Spinelli, Marco Stenta, Andrea Galatini, Cinzia Tavani,