INTRODUCTION OF A METHOXYL GROUP INTO INDOLES AND 2,3-DIHYDROINDOLES - NEW SYNTHESIS OF 5-HYDROXYTRYPTAMINE (SEROTONIN)

被引:31
作者
SAITO, K
KIKUGAWA, Y
机构
[1] Faculty of Pharmaceutical Sciences, Josai University, Saitama, 350-02, 1-1 Keyakidai, Sakado-shi
关键词
D O I
10.1002/jhet.5570160707
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Methoxylation of the 5‐position of indoles and indolines was investigated. Treatment of 5‐bromo‐iodoles and indolines with cuprous iodide and sodium methoxide in methanol/dimethylformamide afforded the corresponding methoxy compounds. This methoxylation reaction was applied to the new synthesis of serotonin. Copyright © 1979 Journal of Heterocyclic Chemistry
引用
收藏
页码:1325 / 1328
页数:4
相关论文
共 24 条
[1]  
AKERMARK B, 1975, J ORG CHEM, V40, P1365, DOI 10.1021/jo00897a048
[2]  
ASERO B, 1952, LIEBIGS ANN CHEM, V576, P69
[3]   SYNTHESIS OF THE 3-2'-AMINOPROPYL-DERIVATIVES AND 3-2'-AMINOBUTYL-DERIVATIVES OF 5-HYDROXYINDOLE, AND AN ALTERNATIVE SYNTHESIS OF 5-HYDROXYTRYPTAMINE [J].
ASH, ASF ;
WRAGG, WR .
JOURNAL OF THE CHEMICAL SOCIETY, 1958, (NOV) :3887-3892
[4]   METAL IONS AND COMPLEXES IN ORGANIC REACTIONS .9. COPPER(1)-CATALYSED CONVERSION OF ARYL HALIDES INTO ALKYL ARYL ETHERS [J].
BACON, RGR ;
RENNISON, SC .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1969, (02) :312-&
[5]   SYNTHESIS OF SOME 5-TRIMETHYLSILYLINDOLES [J].
BELSKY, I ;
GERTNER, D ;
ZILKHA, A .
JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (04) :1348-&
[6]   SYNTHESIS OF O-METHYLATED AND N-METHYLATED DERIVATIVES OF 5-HYDROXYTRYPTAMINE [J].
BENINGTON, F ;
MORIN, RD ;
CLARK, LC .
JOURNAL OF ORGANIC CHEMISTRY, 1958, 23 (12) :1977-1979
[7]   The methoxyindoles and their derivatives [J].
Blaikie, KG ;
Perkin, WH .
JOURNAL OF THE CHEMICAL SOCIETY, 1924, 125 :296-335
[8]   CONVENIENT ALTERNATIVE SYNTHESIS OF 5-HYDROXYTRYPTAMINE [J].
BRETHERICK, L ;
WRAGG, WR ;
GAIMSTER, K .
JOURNAL OF THE CHEMICAL SOCIETY, 1961, (JUL) :2919-&
[9]  
Fischer E., 1883, BERICHTE DTSCH CHEM, V16, P2241
[10]   SYNTHESES OF 7-SUBSTITUTED INDOLINE DERIVATIVES .13. [J].
GALL, WG ;
ASTILL, BD ;
BOEKELHEIDE, V .
JOURNAL OF ORGANIC CHEMISTRY, 1955, 20 (11) :1538-1544