Novel synthesis of 5,6-dihydro-4H-thieno[3,2-b]pyrrol-5-ones via the rhodium(II)-mediated Wolff rearrangement of 3-(thieno-2-yl)-3-oxo-2-diazopropanoates

被引：29

作者：

Lee, DJ

Kim, K ^{[1
]}

Park, YJ

机构：

[1] Seoul Natl Univ, Sch Chem & Mol Engn, Seoul 151742, South Korea

[2] Sook Myung Womens Univ, Dept Chem, Seoul 140742, South Korea

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 06期

关键词：

D O I：

10.1021/ol016995n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Treatment of thioaryolketene S,N-acetals 12 with Hg(OAc)(2) followed by addition of 2-diazo-3-trimethylsilyloxy-3-butenoic acid alkyl esters 15 in CH2Cl2 at room temperature gave 3-(3-alkylamino-5-arylthieno-2-yl)-3-oxo-2-diazopropanoates 16 in good yields. Subsequent reactions of 16 with a catalytic amount of Rh-2(OAc)(4).2H(2)O in benzene at reflux afforded a mixture of 5,6-dihydro-4H-thieno[3,2-b]pyrrol-5-ones 18 and the corresponding enols 19 in excellent yields.

引用

页码：873 / 876

页数：4

共 20 条

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