Combinatorial synthesis of 4-oxo-4H-imidazo[1,5-a]quinoxalines and 4-oxo-4H-pyrazolo[1,5-a]quinoxalines

被引:20
作者
Spatz, Julia H. [1 ,2 ]
Umkehrer, Michael [1 ]
Kalinski, Cedric [1 ]
Ross, Guenther [1 ]
Burdack, Christoph [1 ]
Kolb, Juergen [1 ]
Bach, Thorsten [2 ]
机构
[1] Priaton GmbH, D-81739 Munich, Germany
[2] Tech Univ Munich, D-85747 Garching, Germany
关键词
Ugi-reaction; multi-component reaction; imidazo-quinoxaline; pyrazolo-quinoxaline; nucleophilic aromatic substitution;
D O I
10.1016/j.tetlet.2007.09.015
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A combinatorial synthetic route yielding imidazo[1,5-a]quinoxalines and pyrazolo[1,5-a] quinoxalines is described. The use of 2-fluoroaniline and 1H-imidazole-4-carboxylic acid, respectively, 1H-pyrazole-3-carboxylic acid in the Ugi-reaction (U-4CR) followed by a nucleophilic aromatic substitution (S(N)Ar) affords the imidazo- as well as the pyrazolo-[1,5-a] quinoxaline moiety in good yield and high diversity. (C) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:8060 / 8064
页数:5
相关论文
共 15 条
[1]   Reaction of quinoxalin-2-ones with TosMIC reagent:: synthesis of imidazo[1,5-a]quinoxalin-4-ones [J].
Chen, P ;
Barrish, JC ;
Iwanowicz, E ;
Lin, J ;
Bednarz, MS ;
Chen, BC .
TETRAHEDRON LETTERS, 2001, 42 (26) :4293-4295
[2]   Recent developments in isocyanide based multicomponent reactions in applied chemistry [J].
Dömling, A .
CHEMICAL REVIEWS, 2006, 106 (01) :17-89
[3]  
Dömling A, 1998, COMB CHEM HIGH T SCR, V1, P1
[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]   Liquid-phase combinatorial synthesis of alicyclic β-lactams via Ugi four-component reaction [J].
Gedey, S ;
Van der Eycken, J ;
Fulöp, F .
ORGANIC LETTERS, 2002, 4 (11) :1967-1969
[6]   Strategy and tactics in combinatorial organic synthesis. Applications to drug discovery [J].
Gordon, EM ;
Gallop, MA ;
Patel, DV .
ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (03) :144-154
[7]   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
[8]   Solid-phase organic reactions .2. A review of the literature Nov 95 Nov 96. [J].
Hermkens, PHH ;
Ottenheijm, HCJ ;
Rees, DC .
TETRAHEDRON, 1997, 53 (16) :5643-5678
[9]   A new and versatile Ugi/SNAr synthesis of fused 4,5-dihydrotetrazolo[1,5-a]quinoxalines [J].
Kalinski, C ;
Umkehrer, M ;
Gonnard, S ;
Jäger, N ;
Ross, G ;
Hiller, W .
TETRAHEDRON LETTERS, 2006, 47 (12) :2041-2044
[10]   Multicomponent reactions are accelerated in water [J].
Pirrung, MC ;
Das Sarma, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (02) :444-445