REARRANGEMENT REACTION IN 1-HYDROXYINDOLE CHEMISTRY: A SYNTHESIS OF NOVEL 7-SUBSTITUTED YOHIMBINE, AND 4a-SUBSTITUTED 1,2,3,4-TETRAHYDRO-β-CARBOLINE DERIVATIVES

被引：3

作者：

Yoshino, Katsumasa ^{[1
]}

Yamada, Fumio ^{[2
]}

Noguchi, Koichi ^{[1
]}

Kusuno, Kiyoka ^{[1
]}

Somei, Masanori ^{[1
,3
]}

机构：

[1] Kanazawa Univ, Fac Pharmaceut Sci, Grad Sch Nat Sci & Technol, Kakuma Machi, Kanazawa, Ishikawa 9201192, Japan

[2] Sumika Technoserv Corp, 2-1-4 Takatsukasa, Takarazuka, Hyogo 6650051, Japan

[3] Someiyakko Kenkyusho, 56-7 Matsuhidai, Matsudo, Chiba 2702214, Japan

来源：

HETEROCYCLES | 2019年 / 98卷 / 10期

关键词：

NUCLEOPHILIC-SUBSTITUTION REACTION; INDOLE NUCLEUS; 1-HYDROXYTRYPTAMINE; 1-HYDROXYYOHIMBINE; NITROGEN;

D O I：

10.3987/COM-19-14157

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

X-Ray analyses of 1-hydroxyyohimbine derivatives definitely show the deviation of the N(1)-O bond from the indole molecular plane. This fact supports our working hypothesis "bishomoallylic conjugation". The deviation is responsible for the rearrangement reaction in 1-hydroxyindole chemistry. Effective synthetic method for novel 7 alpha- and 7 beta-heteroarylyohimbine, and 4a alpha- and 4a beta-heteroaryl-1,2,3,4-tetrahydro-beta-carboline derivatives are reported.

引用

页码：1384 / 1407

页数：24

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