Synthesis of 2-substituted-1H-pyrrolo[2,3-b]pyridines: Preparation of 7-azaolivacine analogue and 7-azaindolopyridopyrimidine derivatives.

被引:39
作者
Desarbre, E [1 ]
Coudret, S [1 ]
Meheust, C [1 ]
Merour, JY [1 ]
机构
[1] UNIV ORLEANS,CNRS,INST CHIM ORGAN & ANALYT,F-45067 ORLEANS 2,FRANCE
关键词
INDUSTRIAL SYNTHESIS; EFFICIENT SYNTHESIS; ELLIPTICINE SERIES; INDOLES; GENERATION; LITHIATION; ALKALOIDS; PYRROLES;
D O I
10.1016/S0040-4020(97)00107-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
2-Substituted-1H-pyrrolo[2,3-b]pyridines have been prepared from 7-azaindole by lithiation followed by addition of various electrophiles. A 7-azaolivacine analogue and pyrido[3'2':4,5]pyrrolo[1,2-c]pyrido[3,2-d]pyrimidine have also been prepared. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:3637 / 3648
页数:12
相关论文
共 43 条
[1]   Preparation of organostannanes by intermolecular radical substitution reactions [J].
Aboutayab, K ;
Caddick, S ;
Jenkins, K ;
Joshi, S ;
Khan, S .
TETRAHEDRON, 1996, 52 (34) :11329-11340
[2]   AN EFFICIENT SYNTHESIS OF 2-(2-PYRIDYL)INDOLES BY PALLADIUM(0)-CATALYZED HETEROARYLATION [J].
AMAT, M ;
HADIDA, S ;
BOSCH, J .
TETRAHEDRON LETTERS, 1993, 34 (31) :5005-5006
[3]   INDOLO[2,1-A]ISOQUINOLINES - SYNTHESES, STEROID-HORMONE RECEPTOR-BINDING AFFINITIES, AND CYTOSTATIC ACTIVITY [J].
AMBROS, R ;
SCHNEIDER, MR ;
VONANGERER, S .
JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (01) :153-160
[4]   EFFICIENT SYNTHESIS OF 2-CHLOROINDOLE, 2-BROMOINDOLE, AND 2-IODOINDOLE [J].
BERGMAN, J ;
VENEMALM, L .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (08) :2495-2497
[5]  
Billimoria AD, 1996, HETEROCYCLES, V42, P453
[6]   LITHIATION OF FURO[3,2-C]PYRIDINES AND PYRROLO[3,2-C]PYRIDINES SUBSTITUTED IN THEIR 4 POSITION [J].
BISAGNI, E ;
HUNG, NC ;
LHOSTE, JM .
TETRAHEDRON, 1983, 39 (10) :1777-1781
[7]   2,5-DILITHIATION OF N-PROTECTED IMIDAZOLES - SYNTHESES OF 2,5-DISUBSTITUTED DERIVATIVES OF 1-METHOXYMETHYL-IMIDAZOLE, 1-TRIPHENYLMETHYL-IMIDAZOLE, AND 1-(N,N-DIMETHYLSULPHONAMIDO)-IMIDAZOLE [J].
CHADWICK, DJ ;
NGOCHINDO, RI .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (03) :481-486
[8]  
DALTON L, 1983, J CHEM SOC PERK T 1, P2417, DOI 10.1039/p19830002417
[9]  
DALTON L, 1983, THESIS MANCHESTER
[10]   SYNTHESIS AND REACTIVITY OF 1-SUBSTITUTED-3H-PYRROLO[2,3-B]-PYRIDIN-3-ONE [J].
DESARBRE, E ;
MEROUR, JY .
TETRAHEDRON LETTERS, 1994, 35 (13) :1995-1998