SYNTHESIS AND REACTIONS OF 4,6-DIMETHOXYINDOLE, AN UNUSUAL INDOLE SYSTEM

被引:34
作者
BROWN, VH
SKINNER, WA
DEGRAW, JI
机构
[1] Department of Pharmaceutical Chemistry, Stanford Research Institute, Menlo Park, California
关键词
D O I
10.1002/jhet.5570060414
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A synthesis of 4,6‐dimethoxyindole is described. Formylation or oxalylation reactions gave substitution at position 7 rather than the usual 3‐substitution characteristic of other indoles. A synthesis of N,N‐dimethyl‐4,6‐dimethoxytryptamine is presented along with NMR data for 3 and 7‐substituted compounds in this series. Copyright © 1969 Journal of Heterocyclic Chemistry
引用
收藏
页码:539 / &
相关论文
共 17 条
[1]   TRYPTAMINES, CARBOLINES, AND RELATED COMPOUNDS .2. A CONVENIENT SYNTHESIS OF TRYPTAMINES AND BETA-CARBOLINES [J].
ABRAMOVITCH, RA ;
SHAPIRO, D .
JOURNAL OF THE CHEMICAL SOCIETY, 1956, (NOV) :4589-4592
[2]  
ALLAIS A, 1959, Patent No. 1186258
[3]  
BENINGTON F, 1955, J ORG CHEM, V20, P1456
[4]   DIBORANE AS A REDUCING AGENT .2. REDUCTION OF INDOLE AND PYRROLE CARBONYL DERIVATIVES [J].
BISWAS, KM ;
JACKSON, AH .
TETRAHEDRON, 1968, 24 (03) :1145-&
[5]   BASISCHE DERIVATE DES 4,5,6-TRIMETHOXYINDOLS UND DES 3,4,5-TRIMETHOXYPHENOLS [J].
CARLSSON, A ;
CORRODI, H ;
MAGNUSSON, T .
HELVETICA CHIMICA ACTA, 1963, 46 (04) :1231-&
[6]   PREPARATION OF 5-ALKYLTHIO BRANCHED TRYPTAMINES [J].
HORNER, JK ;
DEGRAW, JI ;
SKINNER, WA .
CANADIAN JOURNAL OF CHEMISTRY, 1966, 44 (03) :307-&
[7]  
JULIA M, 1965, B SOC CHIM FR, P1411
[8]   The peroxide effect in the rearrangement of alpha-bromoacetoacetic ester [J].
Kharasch, MS ;
Sternfeld, E ;
Mayo, FR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1937, 59 :1655-1657
[9]   INDOLES .1. THE FORMYLATION OF INDOLE AND SOME REACTIONS OF 3-FORMYLINDOLE [J].
SMITH, GF .
JOURNAL OF THE CHEMICAL SOCIETY, 1954, (NOV) :3842-3846
[10]   A RELATIONSHIP BETWEEN HALLUCINOGENIC ACTIVITY OF DRUGS AND THEIR ELECTRONIC CONFIGURATION [J].
SNYDER, SH ;
MERRIL, CR .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1965, 54 (01) :258-&