Highly substituted indol-2-ones, quinoxalin-2-ones and benzodiazepin-2,5-diones via a new Ugi(4CR)-Pd assisted N-aryl amidation strategy

被引：59

作者：

Kalinski, C

Umkehrer, M

Ross, G

Kolb, J

Burdack, C

Hiller, W

机构：

[1] Priaton GmbH, D-82327 Tutzing, Germany

[2] Tech Univ Munich, D-85747 Garching, Germany

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 20期

关键词：

Ugi reaction; palladium-assisted intramolecular aryl amidation; heterocycles; combinatorial chemistry;

D O I：

10.1016/j.tetlet.2006.03.069

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new strategy employing an Ugi four-component reaction and a palladium-assisted intramolecular N-aryl amidation reaction is reported. The straight forward two-step synthesis generates N-heterocyclic compounds with four points of diversity from trivial starting materials with acceptable yields. This new reaction is also suitable for the generation of compound libraries. (c) 2006 Elsevier Ltd. All rights reserved.

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页码：3423 / 3426

页数：4

相关论文

共 21 条

[1] Recent developments in isocyanide based multicomponent reactions in applied chemistry [J].

Dömling, A .

CHEMICAL REVIEWS, 2006, 106 (01) :17-89

[2]

Dömling A, 1998, COMB CHEM HIGH T SCR, V1, P1

[3]

Domling A., 2000, ANGEW CHEM, V112, P3300

[4] APPLICATIONS OF COMBINATORIAL TECHNOLOGIES TO DRUG DISCOVERY .1. BACKGROUND AND PEPTIDE COMBINATORIAL LIBRARIES [J].

GALLOP, MA ;

BARRETT, RW ;

DOWER, WJ ;

FODOR, SPA ;

GORDON, EM .

JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (09) :1233-1251

[5] APPLICATIONS OF COMBINATORIAL TECHNOLOGIES TO DRUG DISCOVERY .2. COMBINATORIAL ORGANIC-SYNTHESIS, LIBRARY SCREENING STRATEGIES, AND FUTURE-DIRECTIONS [J].

GORDON, EM ;

BARRETT, RW ;

DOWER, WJ ;

FODOR, SPA ;

GALLOP, MA .

JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (10) :1385-1401

[6] Sequential Ugi/Heck cyclization strategies for the facile construction of highly functionalized N-heterocyclic scaffolds [J].

Gracias, V ;

Moore, JD ;

Djuric, SW .

TETRAHEDRON LETTERS, 2004, 45 (02) :417-420

[7] Postcondensation modifications of Ugi four-component condensation products: 1-Isocyanocyclohexene as a convertible isocyanide. Mechanism of conversion, synthesis of diverse structures, and demonstration of resin capture [J].

Keating, TA ;

Armstrong, RW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (11) :2574-2583

[8] A new resin-bound universal isonitrile for the ugi 4CC reaction: Preparation and applications to the synthesis of 2,5-diketopiperazines and 1,4-benzodiazepine-2,5-diones [J].

Kennedy, AL ;

Fryer, AM ;

Josey, JA .

ORGANIC LETTERS, 2002, 4 (07) :1167-1170

[9] Pairwise use of complexity-generating reactions in diversity-oriented organic synthesis [J].

Lee, DS ;

Sello, JK ;

Schreiber, SL .

ORGANIC LETTERS, 2000, 2 (05) :709-712

[10] A new class of convertible isocyanides in the Ugi four-component reaction [J].

Lindhorst, T ;

Bock, H ;

Ugi, I .

TETRAHEDRON, 1999, 55 (24) :7411-7420