One-Pot and Regioselective Gold-Catalyzed Synthesis of 2-Imidazolyl-1-pyrazolylbenzenes from 1-Propargyl-1H-benzotriazoles, Alkynes and Nitriles through -Imino Gold(I) Carbene Complexes

被引：30

作者：

Gonzalez, Jairo ^{[1
,2
]}

Santamaria, Javier ^{[1
,2
]}

Suarez-Sobrino, Angel L. ^{[1
,2
]}

Ballesteros, Alfredo ^{[1
,2
]}

机构：

[1] Univ Oviedo, Inst Univ Quim Organometal Enrique Moles, C Julian Claveria 8, E-33006 Oviedo, Spain

[2] Univ Oviedo, Dept Quim Organ & Inorgan, C Julian Claveria 8, E-33006 Oviedo, Spain

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2016年 / 358卷 / 09期

关键词：

alkynes; gold catalysis; imidazoles; iminocarbenes; pyrazoles; INTERMOLECULAR NITRENE TRANSFER; NUCLEOPHILIC NITRENOIDS; EFFICIENT; BOND; CYCLOADDITIONS; 2H-AZIRINES; OXAZOLES; YNAMIDES; ACCESS; CONSTRUCTION;

D O I：

10.1002/adsc.201600022

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A three-component gold(I)-catalyzed synthesis of 2-imidazoyl-1-pyrazolylbenzenes from 1-propargyl-1H-benzotriazoles is described here. Initially the benzotriazole derivative suffers an intramolecular 5-endo-dig cyclization to form a triazapentalene. This dipolar compound is able to perform an intermolecular and regioselective attack to a gold-activated alkyne. After triazole breakage, the pyrazole ring and an -imino gold carbene complex are formed. Finally, the iminocarbene is captured by a nitrile to form an imidazole ring.

引用

页码：1398 / 1403

页数：6

共 54 条

[1]

[Anonymous], 2011, ANGEW CHEM

[2] Highly regioselective synthesis of 2,4,5-(hetero) aryl substituted oxazoles by intermolecular [3+2]-cycloaddition of unsymmetrical internal alkynes [J].

Chatzopoulou, Elli ;

Davies, Paul W. .

CHEMICAL COMMUNICATIONS, 2013, 49 (77) :8617-8619

[3] Synthesis and characterization of organogold complexes containing an acid stable Au-C bond through triazole-yne 5-endo-dig cyclization [J].

Chen, Yunfeng ;

Wang, Dawei ;

Petersen, Jeffrey L. ;

Akhmedov, Novruz G. ;

Shi, Xiaodong .

CHEMICAL COMMUNICATIONS, 2010, 46 (33) :6147-6149

[4] Gold-Catalyzed Carbon-Heteroatom Bond-Forming Reactions [J].

Corma, A. ;

Leyva-Perez, A. ;

Sabater, Maria J. .

CHEMICAL REVIEWS, 2011, 111 (03) :1657-1712

[5] Nucleophilic Nitrenoids Through π-Acid Catalysis: Providing a Common Basis for Rapid Access into Diverse Nitrogen Heterocycles [J].

Davies, Paul W. ;

Garzon, Miguel .

ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 4 (08) :694-708

[6] Intermolecular and Selective Synthesis of 2,4,5-Trisubstituted Oxazoles by a Gold-Catalyzed Formal [3+2] Cycloaddition [J].

Davies, Paul W. ;

Cremonesi, Alex ;

Dumitrescu, Lidia .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (38) :8931-8935

[7] Homogeneous Gold-Catalyzed Cyclization Reactions of Alkynes with N- and S-Nucleophiles [J].

Debrouwer, Wouter ;

Heugebaert, Thomas S. A. ;

Roman, Bart I. ;

Stevens, Christian V. .

ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (14-15) :2975-3006

[8] Gold(I)-Catalyzed Activation of Alkynes for the Construction of Molecular Complexity [J].

Dorel, Ruth ;

Echavarren, Antonio M. .

CHEMICAL REVIEWS, 2015, 115 (17) :9028-9072

[9]

Elguero J, 2011, MODERN HETEROCYCLIC CHEMISTRY, VOL 4, P635

[10] Gold-Containing and Gold-Generated 1,n-Dipoles as Useful Platforms toward Cycloadditions and Cyclizations [J].

Garayalde, David ;

Nevado, Cristina .

ACS CATALYSIS, 2012, 2 (07) :1462-1479

← 1 2 3 4 5 6 →