Copper-Catalyzed Tandem Azide-Alkyne Cycloaddition, Ullmann Type C-N Coupling, and Intramolecular Direct Arylation

被引：93

作者：

Pericherla, Kasiviswanadharaju ^{[1
,2
]}

Jha, Amitabh ^{[2
]}

Khungar, Bharti ^{[1
]}

Kumar, Anil ^{[1
]}

机构：

[1] Birla Inst Technol & Sci, Dept Chem, Pilani 333031, Rajasthan, India

[2] Acadia Univ, Dept Chem, Wolfville, NS B4P 2R6, Canada

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 17期

基金：

加拿大自然科学与工程研究理事会;

关键词：

FUNCTIONALIZATION; DERIVATIVES; ARYL;

D O I：

10.1021/ol401655r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A ligand-free copper-catalyzed tandem azide-alkyne cycloaddition (CuAAC), Ullmann-type C-N coupling, and intramolecular direct arylation has been described. The designed strategy resulted in the synthesis of a novel trazole-fused azaheterocycle framework. The reaction gave good yields (59-77%) of 1,2,3-triazole-fused imidazo[1,2-a]pyridines in a single step.

引用

页码：4304 / 4307

页数：4

共 36 条

[1] Copper-catalyzed "click" reaction/direct arylation sequence: Modular syntheses of 1,2,3-triazoles
Ackermann, Lutz
Potukuchi, Harish K.
Landsberg, Dirk
Vicente, Ruben
[J]. ORGANIC LETTERS, 2008, 10 (14) : 3081 - 3084
[2] Regioselective syntheses of fully-substituted 1,2,3-triazoles: the CuAAC/C-H bond functionalization nexus
Ackermann, Lutz
Potukuchi, Harish Kumar
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (20) : 4503 - 4513
[3] Click Chemistry: 1,2,3-Triazoles as Pharmacophores
Agalave, Sandip G.
Maujan, Suleman R.
Pore, Vandana S.
[J]. CHEMISTRY-AN ASIAN JOURNAL, 2011, 6 (10) : 2696 - 2718
[4] DERIVATIVES OF IMIDAZOLE .I. SYNTHESIS AND REACTIONS OF IMIDAZO[1,2-A]PYRIDIENES WITH ANALGESIC ANTIINFLAMMATORY ANTIPYRETIC AND ANTICONVULSANT ACTIVITY
ALMIRANTE, L
POLO, L
MUGNAINI, A
PROVINCIALI, E
RUGARLI, P
BIANCOTTI, A
GAMBA, A
MURMANN, W
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1965, 8 (03) : 305 - +
[5] [Anonymous], COMPREHENSIVE HETERO
[6] Copper in cross-coupling reactions - The post-Ullmann chemistry
Beletskaya, IP
Cheprakov, AV
[J]. COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) : 2337 - 2364
[7] Copper-Catalyzed C-C Bond Formation through C-H Functionalization: Synthesis of Multisubstituted Indoles from N-Aryl Enaminones
Bernini, Roberta
Fabrizi, Giancarlo
Sferrazza, Alessio
Cacchi, Sandro
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (43) : 8078 - 8081
[8] A CuAAC/Ullmann C-C Coupling Tandem Reaction: Copper-Catalyzed Reactions of Organic Azides with N-(2-Iodoaryl)propiolamides or 2-Iodo-N-(prop-2-ynyl)benzenamines
Cai, Qian
Yan, Jiajie
Ding, Ke
[J]. ORGANIC LETTERS, 2012, 14 (13) : 3332 - 3335
[9] Palladium(II)-Catalyzed C-H Activation/C-C Cross-Coupling Reactions: Versatility and Practicality
Chen, Xiao
Engle, Keary M.
Wang, Dong-Hui
Yu, Jin-Quan
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (28) : 5094 - 5115
[10] Recent advances in the transition metal-catalyzed twofold oxidative C-H bond activation strategy for C-C and C-N bond formation
Cho, Seung Hwan
Kim, Ji Young
Kwak, Jaesung
Chang, Sukbok
[J]. CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) : 5068 - 5083

← 1 2 3 4 →