Chemoselective Trimerization of Isocyanides: De Novo Synthesis of 2-Indole-Substituted Quinolines and Pyridines

被引：20

作者：

Bao, Lan ^{[1
,2
,3
,4
]}

Liu, Yu ^{[1
,2
,3
,4
]}

Peng, Jinghan ^{[1
,2
,3
,4
]}

Wang, Yuan ^{[1
,2
,3
,4
]}

Dong, Jinhuan ^{[1
,2
,3
,4
]}

Xu, Xianxiu ^{[1
,2
,3
,4
]}

机构：

[1] Shandong Normal Univ, Coll Chem Chem Engn & Mat Sci, Jinan 250014, Peoples R China

[2] Shandong Normal Univ, Collaborat Innovat Ctr Functionalized Probes Chem, Jinan 250014, Peoples R China

[3] Shandong Normal Univ, Key Lab Mol & Nano Probes, Minist Educ, Jinan 250014, Peoples R China

[4] Shandong Normal Univ, Shandong Prov Key Lab Clean Prod Fine Chem, Jinan 250014, Peoples R China

来源：

ORGANIC LETTERS | 2022年 / 24卷 / 01期

基金：

中国国家自然科学基金;

关键词：

CROSS-CYCLOADDITION; MULTICOMPONENT REACTIONS; DERIVATIVES; ANNULATION; POLYMERS; ROUTE;

D O I：

10.1021/acs.orglett.1c03693

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A catalyst-free chemoselective trimerization reaction of readily available isocyanides is described. This domino reaction provides facile access to a wide range of 2-(indol-2-yl)-quinolines and 2-(indol-2-yl)-pyridines in moderate to excellent yields. A "head to head" heterodimerization of two isocyanides is proposed as the key step of this reaction.

引用

页码：105 / 109

页数：5

共 34 条

[1]

Aumann V. R., 1985, ANGEW CHEM-GER EDIT, V97, P960

[2] A cage-monoterpene indole alkaloid from Alstonia scholaris [J].

Cai, Xiang-Hai ;

Tan, Qin-Gang ;

Liu, Ya-Ping ;

Feng, Tao ;

Du, Zhi-Zhi ;

Li, We-Qi ;

Luo, Xiao-Dong .

ORGANIC LETTERS, 2008, 10 (04) :577-580

[3] Reductive linear- and cyclo-trimerization of isocyanides using an Al-Al-bonded compound [J].

Chen, Weixing ;

Zhao, Yanxia ;

Xu, Wenhua ;

Su, Ji-Hu ;

Shen, Lingyi ;

Liu, Li ;

Wu, Biao ;

Yang, Xiao-Juan .

CHEMICAL COMMUNICATIONS, 2019, 55 (64) :9452-9455

[4] Thienothiophenes, Dithienothiophenes, and Thienoacenes: Syntheses, Oligomers, Polymers, and Properties [J].

Cinar, Mehmet Emin ;

Ozturk, Turan .

CHEMICAL REVIEWS, 2015, 115 (09) :3036-3140

[5] Recent developments in isocyanide based multicomponent reactions in applied chemistry [J].

Dömling, A .

CHEMICAL REVIEWS, 2006, 106 (01) :17-89

[6] Chemistry and Biology Of Multicomponent Reactions [J].

Domling, Alexander ;

Wang, Wei ;

Wang, Kan .

CHEMICAL REVIEWS, 2012, 112 (06) :3083-3135

[7] Versatile tools in the construction of substituted 2,2′-bipyridines-cross-coupling reactions with tin, zinc and boron compounds [J].

Hapke, Marko ;

Brandt, Lars ;

Luetzen, Arne .

CHEMICAL SOCIETY REVIEWS, 2008, 37 (12) :2782-2797

[8] Patent in vitro methicillin-resistant Staphylococcus aureus activity of 2-(1H-indol-3-yl)quinoline derivatives [J].

Hoemann, MZ ;

Kumaravel, G ;

Xie, RL ;

Rossi, RF ;

Meyer, S ;

Sidhu, A ;

Cuny, GD ;

Hauske, JR .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2000, 10 (23) :2675-2678

[9] Silver-Catalyzed Chemoselective [4+2] Annulation of Two Isocyanides: A General Route to Pyridone-Fused Carbo- and Heterocycles [J].

Hu, Zhongyan ;

Dong, Jinhuan ;

Men, Yang ;

Lin, Zhichen ;

Cai, Jinxiong ;

Xu, Xianxiu .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (07) :1805-1809

[10] Cross-Cycloaddition of Two Different Isocyanides: Chemoselective Heterodimerization and [3+2]-Cyclization of 1,4-Diazabutatriene [J].

Hu, Zhongyan ;

Yuan, Haiyan ;

Men, Yang ;

Liu, Qun ;

Zhang, Jingping ;

Xu, Xianxiu .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (25) :7077-7080

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