Reaction of different α-sulfonyl acetamides with methyl acrylate

被引：17

作者：

Chang, MY

Chen, ST ^{[1
]}

Chang, NC

机构：

[1] Acad Sinica, Inst Biol Chem, Taipei 115, Taiwan

[2] Natl Sun Yat Sen Univ, Dept Chem, Kaohsiung 804, Taiwan

来源：

TETRAHEDRON | 2002年 / 58卷 / 25期

关键词：

cycloaddition reaction; alpha-sulfonyl acetamide dianion; methyl acrylate; glutarimides;

D O I：

10.1016/S0040-4020(02)00475-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The base-induced tandem-coupling/cyclization reactions of various a-sulfonyl acetamide derivatives A with methyl acrylate differentiated between two different pathways to form alpha-sulfonyl analogs of glutarimides B and 2-hydroxycyclohexenecarboxylic acid derivatives C in different ratios. The reaction of alpha-sulfonyl acetamide dianion with methyl acrylate depended on three factors: the stability of the dianion, concentration of methyl acrylate and the structure of sufonyl and amide substituents. By changing the reaction conditions, we efficiently controlled the cycloaddition reaction to synthesize the desired product, each of which has potential biological activities. A ring closure mechanism is proposed for the reactions. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：5075 / 5080

页数：6

共 24 条

[1]

BARTA TE, 1999, Patent No. 9925687

[2]

BRANCA Q, 1995, Patent No. 5393875

[3] An efficient synthesis of N-benzyl-3-sulfonyl glutarimides.: Formal synthesis of the aromatase inhibitor AG-1 [J].