A general and highly regio and stereoselective method for the synthesis of (E)-2-(2-arylvinyl)-3,1-benzoxathiin-4-ones through palladium-copper catalysis

被引：10

作者：

Nandi, B ^{[1
]}

Kundu, NG ^{[1
]}

机构：

[1] Indian Assoc Cultivat Sci, Dept Organ Chem, Kolkata 700032, W Bengal, India

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2001年 / 14期

关键词：

D O I：

10.1039/b102306n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A palladium-copper-catalysed procedure for the synthesis of (E)-2-(2-arylvinyl)-3,1-benzoxathiin-4-ones 5a-5h is developed. 3-[2-(Methoxycarbonyl)phenylthio]propyne 2 reacts with aryl iodides 3a-3h in the presence of bis(triphenylphosphine)palladium(ii) dichloride, copper(i) iodide and triethylamine in acetonitrile to furnish the disubstituted alkynes 4a-4h in good yields (70-84%). These on alkaline hydrolysis and subsequent cyclisation of the carboxylic acids formed with copper(i) iodide (20 mol%) and triethylamine in tetrahydrofuran under reflux afford (E)-2-(2-arylvinyl)-3,1-benzoxathiin-4-ones 5a-5h in 61-70% yield rather than the expected benzoxathiepinones 6. The reactions of (E)-2-(2-arylvinyl)-3,1-benzoxathiin-4-ones 5a and 5g with nucleophiles and the hydrogenation of compounds 5a, 5b and 5d are also studied.

引用

页码：1649 / 1655

页数：7

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