Bronsted Acid-Catalyzed Regioselective Carboxamidation of 2-Indolylmethanols with Isonitriles

被引：4

作者：

Chaudhari, Tohasib Yusub ^{[1
]}

Bisht, Somya ^{[1
]}

Chorol, Sonam ^{[2
]}

Bhujbal, Shivkanya Madhavrao ^{[3
]}

Bharatam, Prasad V. ^{[3
]}

Tandon, Vibha ^{[1
]}

机构：

[1] Jawaharlal Nehru Univ, Special Ctr Mol Med, New Delhi 110067, India

[2] Jawaharlal Nehru Univ, Sch Phys Sci, New Delhi 110067, India

[3] Natl Inst Pharmaceut Educ & Res NIPER, Dept Med Chem, Sas Nagar 160062, Punjab, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 15期

关键词：

AMIDE BOND FORMATION; CARBOXYLIC-ACIDS; ENANTIOSELECTIVE CONSTRUCTION; INSERTION SYNTHESIS; ISOCYANATES; INDOLES; CYCLOADDITIONS; CONDENSATION; PEPTIDES; ENAMIDES;

D O I：

10.1021/acs.joc.2c02816

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A regioselective direct carboxamidation reaction of 2-indolylmethanolswith readily available isocyanoesters/isocyanides has been reportedin this work. The reaction was catalyzed by Bronsted acid such as p-TsOH to deliver the benzylic regioselective amides in67-86% yield under mild conditions. The developed methodologyprovides alternative access to traditional metal-free carboxamidationvia C-C and C-O bond formation with high atom economy.Furthermore, the developed approach was diversified to synthesizechiral indole-2-carboxamide derivatives with a moderate enantiomericexcess (61-73% ee) using an (R)-chiral phosphoric acid.

引用

页码：10412 / 10425

页数：14

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