A regiospecific fischer indole reaction with 3-oxo-24-nor-allobetulin

被引：0

作者：

Zakirova, Liana ^{[1
]}

Baikova, Irina ^{[1
]}

Lobov, Alexander ^{[1
]}

Gatilov, Yury ^{[2
]}

Polovyanenko, Dmitriy ^{[2
]}

Kazakova, Oxana ^{[1
]}

机构：

[1] Russian Acad Sci, Ufa Fed Res Ctr, Ufa Inst Chem, Ufa 450054, Russia

[2] NN Vorozhtzov Novosibirsk Inst Organ Chem SB RAS, Novosibirsk, Russia

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 2024年 / 61卷 / 10期

关键词：

ALLOBETULIN;

D O I：

10.1002/jhet.4877

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

First case of regiospecific formation of indole fused with a triterpene scaffold is observed. Starting from 3-oxo-24-nor-allobetulin Fischer reaction with phenylhydrazine under the influence of weak acid catalyst led to 3H-indole (indolenine) 4. This process was accompanied by a change in the configuration of the methyl group at C-4 that was confirmed by x-ray diffraction method. On the other hand, 3,2-indole 5 was synthesized under the influence of strong acid catalyst (using phenylhydrazine hydrochloride in AcOH acid or phenylhydrazine in MeOH with a few drops of HCl). A formation of indolenine and 3,2-indole derivatives of 3-oxo-24-nor-allobetulin. image

引用

页码：1597 / 1601

页数：5

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