SYNTHESIS AND REACTIONS OF DI-HYDROBENZ[B]INDOLIZINES AND TETRA-HYDROBENZ[B]INDOLIZINES

被引:4
作者
TEITEI, T
DALTON, LK
机构
[1] Division of Applied Chemistry, CSIRO Chemical Research Laboratories, Melbourne, VIC, 3001
关键词
D O I
10.1071/CH9690997
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Treatment of 1-(4′,4′-diethoxybutyl)-3-methoxycarbonylindole with ethanolic hydrogen chloride gives in high yield 9-chloro-10-methoxycarbonyl-6,7,8,9-tetra-hydrobenz[b]indolizine which is readily converted into the 6,7-dihydro compound and the fully aromatic 10-methoxycarbonylbenz [b] indolizine. Substitution and addition reactions of these compounds have been studied. A mechanism for the formation of the chlorotetrahydrobenz[b]indolizines is discussed. © 1969, CSIRO. All rights reserved.
引用
收藏
页码:997 / &
相关论文
共 14 条
[1]   SYNTHESIS OF PYRIDOCARBAZOLES FOR ANTI-TUMOUR STUDIES [J].
DALTON, LK ;
DEMERAC, S ;
TEITEI, T .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1969, 22 (01) :185-&
[2]  
GRUNDY J, 1964, STEREOCHEMISTRY, P81
[3]   SUBSTITUTIONAL AND CONFIGURATIONAL EFFECTS ON CHEMICAL SHIFT IN PYRANOID CARBOHYDRATE DERIVATIVES [J].
LEMIEUX, RU ;
STEVENS, JD .
CANADIAN JOURNAL OF CHEMISTRY, 1965, 43 (07) :2059-&
[4]   GAMMA-CHLOROBUTYRALDEHYDE AND ITS DIETHYL ACETAL [J].
LOFTFIELD, RB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1951, 73 (03) :1365-1366
[5]   Synthetic trial on the indol-group, VII: Nitration and bromination of the ss-indol-carboxylic acid ester and a new synthesis of the colouring of the antique purple. [J].
Majima, R ;
Kotake, M .
BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1930, 63 :2237-2245
[6]  
MOSBY WL, 1961, CHEMISTRY HETEROCY 1, P325
[7]   DECARBONYLATION OF 3-INDOLEGLYOXALYL CHLORIDE [J].
PETERSON, PE ;
WOLF, JP ;
NIEMANN, C .
JOURNAL OF ORGANIC CHEMISTRY, 1958, 23 (02) :303-304
[8]   EXPERIMENTS ON THE SYNTHESIS OF THE RING SYSTEMS OF STRYCHNINE AND ALLIED ALKALOIDS .2. [J].
ROBINSON, R ;
SAXTON, JE .
JOURNAL OF THE CHEMICAL SOCIETY, 1952, (MAR) :976-982
[9]   A SYNTHESIS OF SUBSTITUTED 2-3-BENZPYRROCOLINES [J].
ROBINSON, R ;
SAXTON, JE .
JOURNAL OF THE CHEMICAL SOCIETY, 1950, (NOV) :3136-3140
[10]  
RUETGERSWERKE, 1965, Patent No. 1193946