Chemoselective synthesis of α-carboline derivatives via hypervalent iodine-catalyzed [3+3] annulation under metal-free conditions

被引：0

作者：

Wang, Shuowen ^{[1
]}

Li, Rong ^{[1
]}

Chen, Shanping ^{[1
]}

Mao, Guojiang ^{[2
]}

Shao, Wen ^{[1
]}

Deng, Guo-Jun ^{[1
]}

机构：

[1] Xiangtan Univ, Coll Chem, Key Lab Green Organ Synth & Applicat Hunan Prov, Key Lab Environmentally Friendly Chem & Applicat,M, Xiangtan 411105, Peoples R China

[2] Henan Normal Univ, Dept Sch Chem & Chem Engn, Xinxiang 453007, Peoples R China

来源：

GREEN SYNTHESIS AND CATALYSIS | 2024年 / 5卷 / 02期

基金：

中国国家自然科学基金;

关键词：

Hypervalent iodine-catalysis; Annulation; Metal-free; alpha-Carboline; Chemoselectivity; ONE-POT SYNTHESIS; CYCLIZATION; INDOLES; ALKENES; ACCESS;

D O I：

10.1016/j.gresc.2023.01.002

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A strategy for the synthesis of alpha-carboline derivatives from indole-3-carboxaldehydes and 3-aminocyclohex-2enones under metal-free conditions has been developed. The combination use of phenyliodine (III) diacetate (PIDA) and benzoic acid could significantly facilitate the corresponding [3 + 3] annulation process. This newly developed strategy featured unextraordinary chemoselectivity, good functional group tolerance and the preservation of the carbonyl group of the ketone substrates, which offers the possibility for further transformation of the products.

引用

页码：112 / 116

页数：5

共 52 条

[1] γ-Carbolines and their hydrogenated derivatives. 1. Aromatic γ-carbolines: methods of synthesis, chemical and biological properties (review) [J].

Alekseyev, R. S. ;

Kurkin, A. V. ;

Yurovskaya, M. A. .

CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2009, 45 (08) :889-925

[2] Four-component quinazoline synthesis from simple anilines, aromatic aldehydes and ammonium iodide under metal-free conditions [J].

Chen, Jinjin ;

Chang, Dan ;

Xiao, Fuhong ;

Deng, Guo-Jun .

GREEN CHEMISTRY, 2018, 20 (24) :5459-5463

[3] Indole-to-Carbazole Strategy for the Synthesis of Substituted Carbazoles under Metal-Free Conditions [J].

Chen, Shanping ;

Li, Yuxia ;

Ni, Penghui ;

Huang, Huawen ;

Deng, Guo-Jun .

ORGANIC LETTERS, 2016, 18 (20) :5384-5387

[4] Highly Regioselective and Chemoselective [3+3] Annulation of Enaminones with ortho-Fluoronitrobenzenenes: Divergent Synthesis of Aposafranones and Their N-Oxides [J].

Chen, Xue-Bing ;

Huang, Shun-Tao ;

Li, Jie ;

Yang, Qi ;

Yang, Li ;

Yu, Fuchao .

ORGANIC LETTERS, 2021, 23 (08) :3032-3037

[5] Lactic acid-catalyzed fusion of ninhydrin and enamines for the solvent-free synthesis of hexahydroindeno[1,2-b]indole-9,10-diones [J].

Chen, Xuwen ;

Liu, Yunyun .

HETEROCYCLIC COMMUNICATIONS, 2016, 22 (03) :161-163

[6] An iron(ii)-based metalloradical system for intramolecular amination of C(sp2)-H and C(sp3)-H bonds: synthetic applications and mechanistic studies [J].

Das, Sandip Kumar ;

Das, Subrata ;

Ghosh, Supratim ;

Roy, Satyajit ;

Pareek, Monika ;

Roy, Brindaban ;

Sunoj, Raghavan B. ;

Chattopadhyay, Buddhadeb .

CHEMICAL SCIENCE, 2022, 13 (40) :11817-11828

[7] Ir-Catalyzed Intramolecular Transannulation/C(sp2)-H Amination of 1,2,3,4-Tetrazoles by Electrocyclization [J].

Das, Sandip Kumar ;

Roy, Satyajit ;

Khatua, Hillol ;

Chattopadhyay, Buddhadeb .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (27) :8429-8433

[8] Chemistry of ß-Carbolines as Synthetic Intermediates [J].

Dominguez, Gema ;

Perez-Castells, Javier .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (36) :7243-7253

[9] Iodine(III)-Mediated Tandem Acetoxylation-Cyclization of o-Acyl Phenols for the Facile Construction of α-Acetoxy Benzofuranones [J].

Fan, Renhua ;

Sun, Yi ;

Ye, Yang .

ORGANIC LETTERS, 2009, 11 (22) :5174-5177

[10] Organocatalytic asymmetric synthesis of multifunctionalized α-carboline-spirooxindole hybrids that suppressed proliferation in colorectal cancer cells [J].

He, Xiang-Hong ;

Fu, Xue-Ju ;

Zhan, Gu ;

Zhang, Nan ;

Li, Xiang ;

Zhu, Hong-Ping ;

Peng, Cheng ;

He, Gu ;

Han, Bo .

ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (04) :1048-1055

← 1 2 3 4 5 6 →