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

被引：19

作者：

Bianchi, Lara ^{[1
]}

Maccagno, Massimo ^{[1
]}

Petrillo, Giovanni ^{[1
]}

Rizzato, Egon ^{[2
]}

Sancassan, Fernando ^{[1
]}

Severi, Elda ^{[1
]}

Spinelli, Domenico ^{[2
]}

Stenta, Marco ^{[2
]}

Galatini, Andrea ^{[1
]}

Tavani, Cinzia ^{[1
]}

机构：

[1] Univ Genoa, Dipartimento Chim & Chim Ind, I-16146 Genoa, Italy

[2] Univ Bologna, Dipartimento Chim Organ A Mangini, I-40126 Bologna, Italy

来源：

TETRAHEDRON | 2009年 / 65卷 / 01期

关键词：

3-Nitrothiophene; Ring-opening/ring-closing reactions; Ring-enlargement protocol; Sulfur heterocycles; Ring expansion; Thiopyran S; S-dioxides; BUILDING-BLOCKS; BETA-NITROTHIOPHENES; CALCIUM-CHANNEL; FACILE; (2Z,4E)-2-METHYLSULFANYL-5-(1-NAPHTHYL)-4-NITRO-2,4-PENTADIENOATE; NITROBUTADIENES; THIOCHROMANS; ANALOGS; ACCESS; MODEL;

D O I：

10.1016/j.tet.2008.10.046

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(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. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：336 / 343

页数：8

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