一步法2-氨基-1-苯乙酮盐酸盐、醛和巯基乙酸三组分反应高效合成噻唑烷酮

doi:10.1016/S1872-2067(16)62536-6

催化学报 ›› 2016, Vol. 37 ›› Issue (11): 1997-2002.DOI: 10.1016/S1872-2067(16)62536-6

一步法2-氨基-1-苯乙酮盐酸盐、醛和巯基乙酸三组分反应高效合成噻唑烷酮

Asha Vasantrao Chate^a, Akash Gitaram Tathe^a, Prajyot Jayadev Nagtilak^a, Sunil M. Sangle^b, Charansingh H. Gill^a

a 巴巴萨海布·安贝卡马拉特瓦达大学化学系, 奥兰加巴德 431004, 马哈拉施特拉邦, 印度;
b 拉贾拉姆学院, 戈尔哈布尔 416004, 马哈拉施特拉邦, 印度

收稿日期:2016-06-15 修回日期:2016-08-21 出版日期:2016-11-25 发布日期:2016-11-25
通讯作者: Sunil M. Sangle,Tel:+91-240-2403311; Fax:+91-240-2400491; E-mail:chgill16@gmail.com

Efficient approach to thiazolidinones via a one-pot three-component reaction involving 2-amino-1-phenylethanone hydrochloride, aldehyde and mercaptoacetic acid

Asha Vasantrao Chate^a, Akash Gitaram Tathe^a, Prajyot Jayadev Nagtilak^a, Sunil M. Sangle^b, Charansingh H. Gill^a

a Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad-431004, M.S., India;
b Rajaram College, Kolhapur-416004, M.S., India

Received:2016-06-15 Revised:2016-08-21 Online:2016-11-25 Published:2016-11-25
Contact: Sunil M. Sangle,Tel:+91-240-2403311; Fax:+91-240-2400491; E-mail:chgill16@gmail.com

摘要/Abstract

摘要：

采用一步法在二异丙基乙胺存在下由2-氨基-1-苯乙酮盐酸盐、芳香醛和巯基乙酸三组分反应高效合成了噻唑烷酮.该反应显示出很好的化学选择性.首先2-氨基-1-苯乙酮的N原子与芳香醛选择性反应生成席夫碱，然后巯基乙酸的S原子亲核进攻席夫碱的C原子，最后N原子与羧酸基团环加成生成噻唑烷酮.合成的化合物用光谱技术进行了表征.

关键词: 串联反应, 噻唑烷酮, 杂环化合物, N,N-二异丙基乙胺, 成环作用

Abstract:

A highly efficient three-component reaction has been developed for the synthesis of thiazolidinones involving the reaction of 2-amino-1-phenylethanone hydrochloride with an aromatic aldehyde and mercaptoacetic acid in the presence of diisopropylethylamine in a single pot. Critically, this reaction exhibited excellent chemoselectivity, with the nitrogen atom of the 2-amino-1-phenylethanone component reacting selectively with the aromatic aldehyde to give the corresponding Schiff base. Nucleophilic attack at the carbon of the Schiff base by the sulfur atom of mercaptoacetic, followed by a cyclocondensation reaction between the nitrogen and the carboxylic acid moiety afforded the desired thiazolidinones, which were fully characterized by spectroscopic techniques.

Key words: Tandem reaction, Thiazolidinones, Heterocycles, N,N-diisopropylethylamine, Cyclization

Asha Vasantrao Chate, Akash Gitaram Tathe, Prajyot Jayadev Nagtilak, Sunil M. Sangle, Charansingh H. Gill. 一步法2-氨基-1-苯乙酮盐酸盐、醛和巯基乙酸三组分反应高效合成噻唑烷酮[J]. 催化学报, 2016, 37(11): 1997-2002.

Asha Vasantrao Chate, Akash Gitaram Tathe, Prajyot Jayadev Nagtilak, Sunil M. Sangle, Charansingh H. Gill. Efficient approach to thiazolidinones via a one-pot three-component reaction involving 2-amino-1-phenylethanone hydrochloride, aldehyde and mercaptoacetic acid[J]. Chinese Journal of Catalysis, 2016, 37(11): 1997-2002.

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一步法2-氨基-1-苯乙酮盐酸盐、醛和巯基乙酸三组分反应高效合成噻唑烷酮

Efficient approach to thiazolidinones via a one-pot three-component reaction involving 2-amino-1-phenylethanone hydrochloride, aldehyde and mercaptoacetic acid

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