Rapid synthesis of 3-amino-imidazopyridines by a microwave-assisted four-component coupling in one pot

被引：134

作者：

DiMauro, Erin F.

Kennedy, Joseph M.

机构：

[1] Amgen Inc, Dept Med Chem, Cambridge, MA 02139 USA

[2] Boston Coll, Chestnut Hill, MA 02167 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 72卷 / 03期

关键词：

D O I：

10.1021/jo0622072

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The rapid and efficient synthesis of various 2,6-disubstituted-3-amino-imidazopyridines using a microwave-assisted one-pot cyclization/Suzuki coupling approach is described. The utility of a 2-aminopyridine-5-boronic acid pinacol ester as a robust and versatile building block for the synthesis of diverse compound libraries is emphasized. The boronate functional group is remarkably tolerant to the Lewis acid catalyzed cyclizations, and the subsequent Pd(0)-catalyzed Suzuki coupling reactions proceed cleanly in the presence of magnesium salts. This work highlights the vast potential of microwave-assisted, metal-catalyzed, multicomponent reactions.

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页码：1013 / 1016

页数：4

相关论文

共 42 条

[11] CHARACTERIZATION OF THE PHYSICOCHEMICAL PROPERTIES OF THE IMIDAZOPYRIDINE DERIVATIVE ALPIDEM - COMPARISON WITH ZOLPIDEM [J].

GEORGES, GJ ;

VERCAUTEREN, DP ;

EVRARD, GH ;

DURANT, FV ;

GEORGE, PG ;

WICK, AE .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1993, 28 (04) :323-335

[12] Universal solid-phase approach for the immobilization, derivatization, and resin-to-resin transfer reactions of boronic acids [J].

Gravel, M ;

Thompson, KA ;

Zak, M ;

Bérubé, C ;

Hall, DG .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (01) :3-15

[13] Synthesis of imidazo[1,2-a] annulated pyridines, pyrazines and pyrimidines by a novel three-component condensation [J].

Groebke, K ;

Weber, L ;

Mehlin, F .

SYNLETT, 1998, (06) :661-+

[14] 2-amino-3-substituted-6-[(E)-1-phenyl-2-(N-methylcarbamoyl)vinyl]imidazo-[1,2-a]pyridines as a novel class of inhibitors of human rhinovirus:: Stereospecific synthesis and antiviral activity [J].

Hamdouchi, C ;

de Blas, J ;

del Prado, M ;

Gruber, J ;

Heinz, BA ;

Vance, L .

JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (01) :50-59

[15] Synthesis of para-substituted 3-formyl arylboronic esters [J].

Holland, R ;

Spencer, J ;

Deadman, JJ .

SYNTHESIS-STUTTGART, 2002, (16) :2379-2382

[16] Microwave-assisted multi-component synthesis of fused 3-aminoimidazoles [J].

Ireland, SM ;

Tye, H ;

Whittaker, M .

TETRAHEDRON LETTERS, 2003, 44 (23) :4369-4371

[17]

JINNO M, 2006, Patent No. 2006064339

[18]

Jones G., 1996, COMPREHENSIVE HETERO, V8

[19] Synthesis of a TMC-95A ketomethylene analogue by cyclization via intramolecular Suzuki coupling [J].

Kaiser, M ;

Siciliano, C ;

Assfalg-Machleidt, I ;

Groll, M ;

Milbradt, AG ;

Moroder, L .

ORGANIC LETTERS, 2003, 5 (19) :3435-3437

[20] ANTIULCER AGENTS .5. INHIBITION OF GASTRIC H+/K+-ATPASE BY SUBSTITUTED IMIDAZO[1,2-A]PYRIDINES AND RELATED ANALOGS AND ITS IMPLICATION IN MODELING THE HIGH-AFFINITY POTASSIUM-ION BINDING-SITE OF THE GASTRIC PROTON PUMP ENZYME [J].

KAMINSKI, JJ ;

WALLMARK, B ;

BRIVING, C ;

ANDERSSON, BM .

JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (02) :533-541

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