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

被引：62

作者：

Bakherad, Mohammad ^{[1
]}

Nasr-Isfahani, Hossein ^{[1
]}

Keivanloo, Ali ^{[1
]}

Doostmohammadi, Nesa ^{[1
]}

机构：

[1] Shahrood Univ Technol, Dept Chem, Sch Sci, Shahrood, Iran

来源：

TETRAHEDRON LETTERS | 2008年 / 49卷 / 23期

关键词：

Sonogashira coupling; aryl iodide; imidazole; Pd-catalyzed; imidazopyridines;

D O I：

10.1016/j.tetlet.2008.03.141

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of 2-amino-1-(2-propynyl)pyridinium bromide with various iodobenzenes, catalyzed by Pd-Cu, leads to the formation of 2-benzylimidazo[1,2-a]pyridines. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：3819 / 3822

页数：4

共 48 条

[1] PALLADIUM-CATALYZED COUPLING OF ARYL AND VINYL TRIFLATES OR HALIDES WITH 2-ETHYNYLANILINE - AN EFFICIENT ROUTE TO FUNCTIONALIZED 2-SUBSTITUTED INDOLES [J].

ARCADI, A ;

CACCHI, S ;

MARINELLI, F .

TETRAHEDRON LETTERS, 1989, 30 (19) :2581-2584

[2] A novel synthetic route to new 2-aryl-6-methyl[1,3,5]triazino[1,2-d] [1,3,4]thiadiazine-4,7(6H,9H)-dithiones [J].

Bakavoli, M ;

Bakherad, M ;

Heravi, MM .

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2003, 178 (05) :1157-1162

[3]

Bates DK, 1999, HETEROCYCLES, V51, P475

[4] Synthesis and SAR studies of very potent imidazopyridine antiprotozoal agents [J].

Biftu, T ;

Feng, D ;

Fisher, M ;

Liang, GB ;

Qian, XX ;

Scribner, A ;

Dennis, R ;

Lee, S ;

Liberator, PA ;

Brown, C ;

Gurnett, A ;

Leavitt, PS ;

Thompson, D ;

Mathew, J ;

Misura, A ;

Samaras, S ;

Tamas, T ;

Sina, JF ;

McNulty, KA ;

McKnight, CG ;

Schmatz, DM ;

Wyvratt, M .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (09) :2479-2483

[5]

Bouyssi D, 1997, SYNLETT, P944

[6] Poly(aryleneethynylene)s: Syntheses, properties, structures, and applications [J].

Bunz, UHF .

CHEMICAL REVIEWS, 2000, 100 (04) :1605-1644

[7] 2,3-Diarylimidazo[1,2-a]pyridines as potential inhibitors of UV-induced keratinocytes apoptosis:: synthesis, pharmacological properties and interactions with model membranes and oligonucleotides by NMR [J].

Enguehard-Gueiffier, C ;

Fauvelle, F ;

Debouzy, JC ;

Peinnequin, A ;

Thery, I ;

Dabouis, V ;

Gueiffier, A .

EUROPEAN JOURNAL OF PHARMACEUTICAL SCIENCES, 2005, 24 (2-3) :219-227

[8] Sonogashira coupling reactions of highly oxygenated vinyl halides: The first synthesis of harveynone and epi-harveynone [J].

Graham, AE ;

McKerrecher, D ;

Davies, DH ;

Taylor, RJK .

TETRAHEDRON LETTERS, 1996, 37 (41) :7445-7448

[9] The chemistry of enediynes, enyne allenes and related compounds [J].

Grissom, JW ;

Gunawardena, GU ;

Klingberg, D ;

Huang, DH .

TETRAHEDRON, 1996, 52 (19) :6453-6518

[10] Imidazo[1,2-a]pyridines with potent activity against herpesviruses [J].

Gudmundsson, Kristian S. ;

Johns, Brian A. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (10) :2735-2739

← 1 2 3 4 5 →