A novel three-component reaction of N-fluoropyridinium salts:: a facile approach to imidazo[1,2-a]pyridines

被引：32

作者：

Kiselyov, AS ^{[1
]}

机构：

[1] Chem Divers, Small Mol Drug Discovery, San Diego, CA 92121 USA

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 26期

关键词：

N-fluoropyridinium; three-component condensation; imidazo[1,2-a]pyridine; isonitrile; carbene;

D O I：

10.1016/j.tetlet.2005.04.124

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of N-fluoropyridinium triflate with isonitriles in acetonitrile and propionitrile in the presence of NaBH(OAC)(3) led to the formation of the corresponding imidazo[1,2-a]pyridines in 44-73% yields. The proposed reaction mechanism involves the intermediate formation of a highly reactive carbene species and apparent reduction of the pyridinium intermediate with NaBH(OAC)(3) to yield the targeted heterocycles. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：4487 / 4490

页数：4

共 16 条

[1] Universal Rink-isonitrile resin:: application for the traceless synthesis of 3-acylamino imidazo[1,2-a] pyridines [J].

Chen, JJ ;

Golebiowski, A ;

McClenaghan, J ;

Klopfenstein, SR ;

West, L .

TETRAHEDRON LETTERS, 2001, 42 (12) :2269-2271

[2] UTILIZING ACETYL HYPOFLUORITE FOR CHLORINATION, BROMINATION, AND ETHERIFICATION OF THE PYRIDINE SYSTEM [J].

HEBEL, D ;

ROZEN, S .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (22) :6298-6301

[3] CHLORINATION, BROMINATION, AND OXYGENATION OF THE PYRIDINE RING USING ACOF MADE FROM F2 [J].

HEBEL, D ;

ROZEN, S .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (05) :1123-1125

[4] CARBOXAMIDATION OF PYRIDINES BY THE SYSTEM OF ELEMENTAL FLUORINE-CARBONITRILE-WATER - A USEFUL ALTERNATIVE TO THE CHICHIBABIN AMINATION [J].

KISELYOV, AS ;

STREKOWSKI, L .

SYNTHETIC COMMUNICATIONS, 1994, 24 (16) :2387-2392

[5] Reaction of N-fluoropyridinium fluoride with isonitriles:: a convenient route to picolinamides [J].

Kiselyov, AS .

TETRAHEDRON LETTERS, 2005, 46 (13) :2279-2282

[6] SYNTHESIS OF 2-SUBSTITUTED PYRIDINES BY THE REACTION OF N-FLUOROPYRIDINIUM FLUORIDE WITH TRIMETHYLSILYL DERIVATIVES [J].

KISELYOV, AS ;

STREKOWSKI, L .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (16) :4476-4478

[7] A HIGHLY REGIOSELECTIVE REACTION OF N-FLUOROPYRIDINIUM SALTS WITH STABILIZED SULFUR, OXYGEN, AND NITROGEN NUCLEOPHILES - A CONVENIENT ROUTE TO 2-SUBSTITUTED PYRIDINES [J].

KISELYOV, AS ;

STREKOWSKI, L .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1993, 30 (05) :1361-1364

[8] EFFICIENT HYDROLYSIS OF DITHIOACETALS BY THE N-FLUORO-2,4,6-TRIMETHYLPYRIDINIUM TRIFLATE-WATER SYSTEM [J].

KISELYOV, AS ;

STREKOWSKI, L ;

SEMENOV, VV .

TETRAHEDRON, 1993, 49 (11) :2151-2158

[9]

KISELYOV AS, 1992, MENDELEEV COMMUN, P128

[10]

KISELYOV AS, 1994, SYNTHETIC COMMUN, V35, P8951

← 1 2 →