Microwave-Assisted Synthesis of Tetrahydro-β-carbolines and β-Carbolines

被引：55

作者：

Eagon, Scott ^{[1
]}

Anderson, Marc O. ^{[1
]}

机构：

[1] San Francisco State Univ, Dept Chem & Biochem, San Francisco, CA 94132 USA

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 2014卷 / 08期

基金：

美国国家科学基金会;

关键词：

Synthetic methods; Microwave chemistry; Nitrogen heterocycles; PICTET-SPENGLER CONDENSATION; IN-VITRO; DERIVATIVES; ALKALOIDS; EFFICIENT; DESIGN; BROMINATION; INHIBITORS; CATALYST; ROUTE;

D O I：

10.1002/ejoc.201301580

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A microwave-mediated Pictet-Spengler procedure utilizing 1,2-dichloroethane (DCE) and trifluoroacetic acid (TFA) was developed to provide tetrahydro--carboline salts in high yields. Reactions are complete in 20 minutes or less and the product precipitates from solution in high yields and purity, negating the need for liquid-liquid extraction or column chromatography. This method tolerates a wide range of functionality and can be performed on milligram to gram scales. A subsequent microwave-mediated aromatization of the synthesized tetrahydro--carbolines to -carbolines was also developed utilizing catalytic Pd/C. The aromatization is complete in 60 min or less with most substrates requiring minimal purification.

引用

页码：1653 / 1665

页数：13

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