A new route to thiopyran S, S-dioxide derivatives via an overall ring-enlargement protocol from 3-nitrothiophene

(1 E,3 Z)-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...

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Bibliographic Details
Published in:Tetrahedron 2009-01, Vol.65 (1), p.336-343
Main Authors: Bianchi, Lara, Maccagno, Massimo, Petrillo, Giovanni, Rizzato, Egon, Sancassan, Fernando, Severi, Elda, Spinelli, Domenico, Stenta, Marco, Galatini, Andrea, Tavani, Cinzia
Format: Article
Language:English
Subjects:
3-Nitrothiophene
Ring expansion
Ring-enlargement protocol
Ring-opening/ring-closing reactions
Sulfur heterocycles
Thiopyran S, S-dioxides
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Summary:(1 E,3 Z)-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 Ca 2+-channel blockers. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2008.10.046