Intramolecular [4+2]-cycloaddition reactions of cyclic 2-thiomethyl-5-amidofurans

被引：19

作者：

Ginn, JD ^{[1
]}

Lynch, SM ^{[1
]}

Padwa, A ^{[1
]}

机构：

[1] Emory Univ, Dept Chem, Atlanta, GA 30322 USA

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 49期

基金：

美国国家卫生研究院; 美国国家科学基金会;

关键词：

amidofuran; Diels-Alder; intramolecular; DMTSF; pummerer; cyclization;

D O I：

10.1016/S0040-4039(00)01455-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cyclic 2-thiomethyl-5-amidofurans possessing tethered pi -bonds were prepared by a dimethyl(methylthio) sulfonium tetrafluoroborate (DMTSF) induced cyclization of various amido dithioacetals. Upon heating, these systems undergo an intramolecular 4+2-cycloaddition reaction. The initially formed Diels-Alder cycloadduct further rearranges by ring opening of the oxygen bridge followed by a subsequent 1,2-thiomethyl shift. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：9387 / 9391

页数：5

共 19 条

[1]

CALLAGHAN O, 1998, J AM CHEM SOC, V120, P13523

[2]

Jacobi P. A., 1992, ADV HETEROCYCLIC NAT, V2, P251

[3] SOLVENT EFFECTS IN INTRAMOLECULAR DIELS-ALDER REACTIONS OF 2-FURFURYL METHYL FUMARATES - EVIDENCE FOR A POLAR TRANSITION-STATE [J].