Rhodium-catalyzed annulation between 2-arylimidazo[1,2-a]pyridines and alkynes leading to pyrido[1,2-a]benzimidazole derivatives

被引：42

作者：

Peng, Haibo ^{[1
]}

Yu, Jin-Tao ^{[1
]}

Jiang, Yan ^{[1
]}

Wang, Lei ^{[1
]}

Cheng, Jiang ^{[1
]}

机构：

[1] Changzhou Univ, Sch Petrochem Engn, Jiangsu Key Lab Adv Catalyt Mat & Technol, Jiangsu Prov Key Lab Fine Petrochem Engn, Changzhou 213164, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2015年 / 13卷 / 19期

基金：

中国国家自然科学基金;

关键词：

C-H ACTIVATION; N BOND FORMATION; POLYSUBSTITUTED NAPHTHALENE DERIVATIVES; RH(III)-CATALYZED OXIDATIVE ANNULATION; INTERNAL ALKYNES; DIRECTING GROUP; SUBSTITUTED NAPHTHALENES; REGIOSELECTIVE SYNTHESIS; ISOQUINOLONE SYNTHESIS; MOLECULAR-OXYGEN;

D O I：

10.1039/c5ob00450k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A rhodium-catalyzed annulation between 2-arylimidazo[1,2-a] pyridines and alkynes was developed, leading to pyrido[1,2-a] benzimidazole derivatives in moderate to excellent yields. Notably, the ring C in pyrido[1,2-a] benzimidazole and the naphthalene framework were constructed consecutively, which provided a potential pathway leading to such a structure. This procedure tolerated chloro, bromo, cyano and methoxycarbonyl groups.

引用

页码：5354 / 5357

页数：4

共 63 条

[1] Ruthenium-Catalyzed C-H/N-O Bond Functionalization: Green Isoquinolone Syntheses in Water [J].

Ackermann, Lutz ;

Fenner, Sabine .

ORGANIC LETTERS, 2011, 13 (24) :6548-6551

[2] Ruthenium-catalyzed aerobic oxidative coupling of alkynes with 2-aryl-substituted pyrroles [J].

Ackermann, Lutz ;

Wang, Lianhui ;

Lygin, Alexander V. .

CHEMICAL SCIENCE, 2012, 3 (01) :177-180

[3] Ruthenium-Catalyzed Oxidative Annulation by Cleavage of C-H/N-H Bonds [J].

Ackermann, Lutz ;

Lygin, Alexander V. ;

Hofmann, Nora .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (28) :6379-6382

[4] Ruthenium-Catalyzed Oxidative Synthesis of 2-Pyridones through C-H/N-H Bond Functionalizations [J].

Ackermann, Lutz ;

Lygin, Alexander V. ;

Hofmann, Nora .

ORGANIC LETTERS, 2011, 13 (12) :3278-3281

[5] Synthesis of pyrido[1,2-a]benzimidazoles by photo-stimulated C-N bond formation via SRN1 reactions [J].

Barolo, Silvia M. ;

Wang, You ;

Rossi, Roberto A. ;

Cuny, Gregory D. .

TETRAHEDRON, 2013, 69 (26) :5487-5494

[6] Synthesis, arrangement, and reactivity of arene-lanthanide compounds [J].

Bochkarev, MN .

CHEMICAL REVIEWS, 2002, 102 (06) :2089-2117

[7] TMIO-Pyrlmid Hybrids are Profluorescent, Site-Directed Spin Labels for Nucleic Acids [J].

Chalmers, Benjamin A. ;

Saha, Subham ;

Tri Nguyen ;

McMurtrie, John ;

Sigurdsson, Snorri Th. ;

Bottle, Steven E. ;

Masters, Kye-Simeon .

ORGANIC LETTERS, 2014, 16 (21) :5528-5531

[8] The Copper-Catalyzed C-3-Formylation of Indole C-H Bonds using Tertiary Amines and Molecular Oxygen [J].

Chen, Jianbin ;

Liu, Bin ;

Liu, Dongfang ;

Liu, Shan ;

Cheng, Jiang .

ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (13) :2438-2442

[9] Rhodium-Catalyzed Direct Annulation of Aldehydes with Alkynes Leading to Indenones: Proceeding through in Situ Directing Group Formation and Removal [J].

Chen, Shuyou ;

Yu, Jintao ;

Jiang, Yan ;

Chen, Fan ;

Cheng, Jiang .

ORGANIC LETTERS, 2013, 15 (18) :4754-4757

[10] Ruthenium-Catalyzed Highly Regioselective Cyclization of Ketoximes with Alkynes by C-H Bond Activation: A Practical Route to Synthesize Substituted Isoquinolines [J].

Chinnagolla, Ravi Kiran ;

Pimparkar, Sandeep ;

Jeganmohan, Masilamani .

ORGANIC LETTERS, 2012, 14 (12) :3032-3035

← 1 2 3 4 5 6 7 →