A Diels-Alder strategy for the building of imidazo[4,5-g]quinoline-4,9-dione derivatives

被引:7
作者
Alvarez, F
Taleb, A
Gentili, J
Nebois, P
Terreux, R
Domard, M
Thozet, A
Merle, D
Fillion, H
Walchshofer, N
机构
[1] Univ Lyon 1, ISPB, EA 3741, Ecosyst & Mol Bioact, F-69373 Lyon, France
[2] Univ Lyon 1, Crystallog Lab, CNRS, F-69622 Villeurbanne, France
关键词
benzimidazole; cycloaddition; nitrogen heterocycles; quinones;
D O I
10.1002/ejoc.200400803
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Benzimidazole-4,7-diones 3a and 3b were synthesized and submitted to hetero Diels-Alder reactions with azadienes 4 and 5 to afford imidazo[4,5-g]quinoline-4,9-diones 6-9. The structure of the latter was assigned by X-ray diffraction, H-1 NMR NOE DIFF experiments or by a molecular dynamics study. (c) Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:1903 / 1908
页数:6
相关论文
共 27 条
[1]   Benzimidazole-4,7-diones as inhibitors of protozoal (Toxoplasma gondii) purine nucleoside phosphorylase [J].
Alvarez, F ;
Ghérardi, A ;
Nebois, P ;
Sarciron, ME ;
Pétavy, AF ;
Walchshofer, N .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2002, 12 (06) :977-979
[2]  
Alvarez M, 2000, EUR J ORG CHEM, V2000, P849
[3]  
Bouaziz Z, 2002, EUR J ORG CHEM, V2002, P1834, DOI 10.1002/1099-0690(200206)2002:11<1834::AID-EJOC1834>3.0.CO
[4]  
2-K
[5]   Recent developments in imino Diels-Alder reactions [J].
Buonora, P ;
Olsen, JC ;
Oh, T .
TETRAHEDRON, 2001, 57 (29) :6099-6138
[6]  
Carl-Wolfgang S., 1963, US, Patent No. 3084165
[7]   Regiospecific hetero Diels-Alder synthesis of furo[2,3-g] and furo[3,2-g]quinoline-4,9-diones [J].
Cherkaoui, O ;
Nebois, P ;
Fillion, H ;
Domard, M ;
Fenet, B .
TETRAHEDRON, 1996, 52 (28) :9499-9508
[8]   A REGIOSELECTIVE SYNTHESIS OF 4,5-DISUBSTITUTED AND 4,8-DISUBSTITUTED AZA-ANTHRAQUINONES BY THE DIELS-ALDER ROUTE [J].
CHIGR, M ;
FILLION, H ;
ROUGNY, A .
TETRAHEDRON LETTERS, 1988, 29 (46) :5913-5916
[9]   Development of novel quinone phosphorodiamidate prodrugs targeted to DT-diaphorase [J].
Flader, C ;
Liu, JW ;
Borch, RF .
JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (16) :3157-3167
[10]   REPRESENTATION OF VANDERWAALS (VDW) INTERACTIONS IN MOLECULAR MECHANICS FORCE-FIELDS - POTENTIAL FORM, COMBINATION RULES, AND VDW PARAMETERS [J].
HALGREN, TA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (20) :7827-7843