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

共 50 条

[1] Lewis Acid Catalyzed Regioselective Substitution of 2-Indolylmethanols with Pyrroles
Gao, Jun-Nan
Tan, Wen-Xin
Yang, Shuang
Wang, Ning-Yi
Han, Jiebin
Wang, Da-Hua
Zhang, Yu-Chen
Shi, Feng
SYNTHESIS-STUTTGART, 2025, 57 (06): : 1189 - 1198
[2] Synthesis of C3-functionalized indole derivatives via Bronsted acid-catalyzed regioselective arylation of 2-indolylmethanols with guaiazulene
Liu, Yang
Cao, Meng
Zhang, Shangxi
Wang, Zhenxi
Dai, Xin
Jiang, Xinde
Dong, Yucheng
Fu, Jie
ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (07) : 1510 - 1517
[3] Bronsted acid-catalyzed regioselective reactions of 2-indolylmethanols with cyclic enaminone and anhydride leading to C3-functionalized indole derivatives
Li, Can
Zhang, Hong-Hao
Fan, Tao
Shen, Yang
Wu, Qiong
Shi, Feng
ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (29) : 6932 - 6936
[4] Lewis Acid-Catalyzed (3+2) Cycloaddition of 2-Indolylmethanols with β,γ-Unsaturated α-Ketoesters
Yang, Shuang
Wang, Hai-Qing
Gao, Jun-Nan
Tan, Wen-Xin
Zhang, Yu-Chen
Shi, Feng
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (35)
[5] Regioselective Reaction of 2-Indolylmethanols with Enamides
Tian, Yuting
He, Dongqing
Gao, Limei
Zou, Yu
Liu, Xiaoshuang
Wang, Qiang
Liang, Enxiang
Zheng, Yongsheng
MOLECULES, 2023, 28 (08):
[6] BrOnsted Acid Catalyzed C3-Alkylation of 2-Indolylmethanols with Azlactones via an Umpolung Strategy
Shen, Yang
Zhu, Zi-Qi
Liu, Jin-Xi
Yu, Lei
Du, Bai-Xiang
Mei, Guang-Jian
Shi, Feng
SYNTHESIS-STUTTGART, 2017, 49 (17): : 4025 - 4034
[7] BrOnsted Acid Catalyzed Dehydrative Nucleophilic Substitution of C3-Substituted 2-Indolylmethanols with Azlactones
Bian, Chen-Yu
Li, Dan
Shi, Qian
Mei, Guang-Jian
Shi, Feng
SYNTHESIS-STUTTGART, 2018, 50 (02): : 295 - 302
[8] Lewis Acid-Controlled Regioselective Phosphorylation of 2-Indolylmethanols with Diarylphosphine Oxides: Synthesis of Highly Substituted Indoles
Hu, Chen
Hong, Gang
He, Yuchen
Zhou, Chen
Kozlowski, Marisa C.
Wang, Limin
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (08): : 4739 - 4753
[9] ACID-CATALYZED SOLVOLYSIS OF ISONITRILES .1.
LIM, YY
STEIN, AR
CANADIAN JOURNAL OF CHEMISTRY, 1971, 49 (14): : 2455 - &
[10] Bronsted acid-catalyzed imine amidation
Rowland, GB
Zhang, HL
Rowland, EB
Chennamadhavuni, S
Wang, Y
Antilla, JC
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (45) : 15696 - 15697

← 1 2 3 4 5 →