Silver-Catalyzed Cyclization of N-(Prop-2-yn-1-yl) pyridin-2-amines

被引：43

作者：

Chioua, Mourad ^{[1
]}

Soriano, Elena ^{[2
]}

Infantes, Lourdes ^{[3
]}

Luisa Jimeno, M. ^{[4
]}

Marco-Contelles, Jose ^{[1
]}

Samadi, Abdelouahid ^{[1
]}

机构：

[1] CSIC, IQOG, Lab Quim Med, Madrid 28006, Spain

[2] CSIC, IQOG, SEPCO, E-28006 Madrid, Spain

[3] CSIC, Inst Quim Fis Rocasolano, E-28006 Madrid, Spain

[4] CSIC, CENQUIOR, E-28006 Madrid, Spain

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 2013卷 / 01期

关键词：

Amines; Nitrogen heterocycles; Silver; Cyclization; Reaction mechanisms; ONE-POT SYNTHESIS; DERIVATIVES; 3-COMPONENT; HETEROCYCLIZATION; ALDEHYDES; AFFINITY; SERIES;

D O I：

10.1002/ejoc.201201258

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report herein the silver-catalyzed cycloisomerization of readily available N-(prop-2-yn-1-yl) pyridine-2-amines as a new and practical method for the synthesis of differently substituted 3-methylimidazo[1,2-a] pyridines. The isomerization reactions proceeded under mild reactions conditions to give good yields and excellent regioselectivity. A DFT-based mechanistic analysis is also reported.

引用

收藏

页码：35 / 39

页数：5

相关论文

共 48 条

[1] Microwave-Assisted, One-Pot Reaction of Pyridines, α-Bromoketones and Ammonium Acetate: An Efficient and Simple Synthesis of Imidazo[1,2-a]-pyridines [J].

Adib, Mehdi ;

Mohamadi, Ali ;

Sheikhi, Ehsan ;

Ansari, Samira ;

Bijanzadeh, Hamid Reza .

SYNLETT, 2010, (11) :1606-1608

[2] Sequential alkylation/gold-catalyzed annulation reactions of anilines with propargylic bromide derivatives [J].

Alfonsi, Maria ;

Arcadi, Antonio ;

Chiarini, Marco ;

Marinelli, Fabio .

TETRAHEDRON LETTERS, 2011, 52 (40) :5145-5148

[3] IMIDAZOLE DERIVATIVES .4. SYNTHESIS AND PHARMACOLOGIC ACTIVITY OF OXYGENATED DERIVATIVES OF IMIDAZO[1,2-ALPHA]PYRIDINE [J].

ALMIRANTE, L ;

MUGNAINI, A ;

DETOMA, N ;

GAMBA, A ;

MURMANN, W ;

HIDALGO, J .

JOURNAL OF MEDICINAL CHEMISTRY, 1970, 13 (06) :1048-+

[4] Pd-Cu catalyzed heterocyclization during Sonogashira coupling:: synthesis of 2-benzylimidazo[1,2-a]pyridine [J].

Bakherad, Mohammad ;

Nasr-Isfahani, Hossein ;

Keivanloo, Ali ;

Doostmohammadi, Nesa .

TETRAHEDRON LETTERS, 2008, 49 (23) :3819-3822

[5] Imidazo[1,2-α]pyridines.: Part 2:: SAR and optimisation of a potent and selective class of cyclin-dependent kinase inhibitors [J].

Byth, KF ;

Culshaw, JD ;

Green, S ;

Oakes, SE ;

Thomas, AP .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (09) :2245-2248

[6] Solid-phase synthesis of imidazo[1,2-a]pyridine using sodium benzenesulfinate as a traceless linker [J].

Chen, Y ;

Lam, YL ;

Lai, YH .

ORGANIC LETTERS, 2002, 4 (22) :3935-3937

[7] Synthetic entries to substituted bicyclic pyridones [J].

Cheng, Dachen ;

Croft, Laura ;

Abdi, Muna ;

Lightfoot, Andrew ;

Gallagher, Timothy .

ORGANIC LETTERS, 2007, 9 (25) :5175-5178

[8]

Chernyak N., 2010, Angew. Chem, V122, P2803, DOI 10.1002/ange.200907291

[9] General and Efficient Copper-Catalyzed Three-Component Coupling Reaction towards Imidazoheterocycles: One-Pot Synthesis of Alpidem and Zolpidem [J].

Chernyak, Natalia ;

Gevorgyan, Vladimir .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (15) :2743-2746

[10]

Couty F., 2008, Comprehensive Heterocyclic Chemistry III, V11, P409, DOI DOI 10.1016/B978-008044992-0.01010-5

← 1 2 3 4 5 →