De Novo Synthesis of Imidazoles by Visible-Light-Induced Photocatalytic Aerobic Oxidation/[3+2] Cycloaddition/Aromatization Cascade

被引：55

作者：

Deng, Qiao-Hui ^{[1
,2
]}

Zou, You-Quan ^{[1
,2
]}

Lu, Liang-Qiu ^{[1
,2
]}

Tang, Zi-Long ^{[3
]}

Chen, Jia-Rong ^{[1
,2
]}

Xiao, Wen-Jing ^{[1
,2
,3
]}

机构：

[1] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China

[2] Collaborat Innovat Ctr Chem Sci & Engn, Tianjin 300072, Peoples R China

[3] Hunan Univ Sci & Technol, Sch Chem & Chem Engn, Xiangtan 411201, Peoples R China

来源：

CHEMISTRY-AN ASIAN JOURNAL | 2014年 / 9卷 / 09期

基金：

美国国家科学基金会;

关键词：

cascade; cycloaddition; imidazoles; oxidation; photochemistry; ALPHA-METALATED ISOCYANIDES; COMBRETASTATIN A-4 ANALOGS; PHOTOREDOX CATALYSIS; C-C; DUAL CATALYSIS; MULTICOMPONENT REACTIONS; REGIOSELECTIVE SYNTHESIS; COMBINING PHOTOREDOX; ANTITUMOR-ACTIVITY; BOND FORMATION;

D O I：

10.1002/asia.201402443

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A visible-light-induced photocatalytic aerobic oxidation/[3+2] cycloaddition/aromatization cascade between secondary amines and isocyanides has been successfully developed. The reaction provides a general and efficient access to diversely substituted imidazoles and imidazo[1,5-a] quinoxalin-4(5 H)-ones in good yields under mild conditions.

引用

页码：2432 / 2435

页数：4

共 76 条

[1] Aryl-aryl bond formation by transition-metal-catalyzed direct arylation
Alberico, Dino
Scott, Mark E.
Lautens, Mark
[J]. CHEMICAL REVIEWS, 2007, 107 (01) : 174 - 238
[2] [Anonymous], 1977, ANGEW CHEM
[3] Regioselective synthesis of 1,5-diaryl-1H-imidazoles by palladium-catalyzed direct arylation of 1-aryl-1H-imidazoles
Bellina, F
Cauteruccio, S
Mannina, L
Rossi, R
Viel, S
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (10) : 3997 - 4005
[4] Development and application of effective protocols for the synthesis of arylheteroarenes and biheteroaryls, including bioactive derivatives, by highly regioselective transition metal-catalyzed direct intermolecular arylation reactions of five-membered heteroarenes with (hetero)aryl halides
Bellina, Fabio
Cauteruccio, Silvia
Rossi, Renzo
[J]. CURRENT ORGANIC CHEMISTRY, 2008, 12 (09) : 774 - 790
[5] Synthesis and biological activity of vicinal diaryl-substituted 1H-imidazoles
Bellina, Fabio
Cauteruccio, Silvia
Rossi, Renzo
[J]. TETRAHEDRON, 2007, 63 (22) : 4571 - 4624
[6] Novel imidazole-based combretastatin A-4 analogues: Evaluation of their in vitro antitumor activity and molecular modeling study of their binding to the colchicine site of tubulin
Bellina, Fabio
Cauteruccio, Silvia
Monti, Susanna
Rossi, Renzo
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (22) : 5757 - 5762
[7] Regioselective Functionalization of the Imidazole Ring via Transition Metal-Catalyzed C-N and C-C Bond Forming Reactions
Bellina, Fabio
Rossi, Renzo
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (08) : 1223 - 1276
[8] Regioselective Synthesis of 4,5-Diaryl-1-methyl-1H-imidazoles Including Highly Cytotoxic Derivatives by Pd-Catalyzed Direct C-5 Arylation of 1-Methyl-1H-imidazole with Aryl Bromides
Bellina, Fabio
Cauteruccio, Silvia
Di Fiore, Annarita
Rossi, Renzo
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (32) : 5436 - 5445
[9] A new strategy for the construction of the imidazo[1,5-a]quinoxalin-4-one ring system and its application to the efficient synthesis of BMS-238497, a novel and potent Lck inhibitor
Chen, BC
Zhao, RL
Bednarz, MS
Wang, B
Sundeen, JE
Barrish, JC
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (03) : 977 - 979
[10] A new facile method for the synthesis of 1-arylimidazole-5-carboxylates
Chen, BC
Bednarz, MS
Zhao, RL
Sundeen, JE
Chen, P
Shen, ZQ
Skoumbourdis, AP
Barrish, JC
[J]. TETRAHEDRON LETTERS, 2000, 41 (29) : 5453 - 5456

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