REACTION OF ETHYL ACYLINDOLE-2-CARBOXYLATES WITH THALLIUM TRINITRATE (SYNTHETIC STUDIES ON INDOLES AND RELATED-COMPOUNDS .33.

被引：0

作者：

TANI, M ^{[1
]}

MATSUMOTO, S ^{[1
]}

AIDA, Y ^{[1
]}

ARIKAWA, S ^{[1
]}

NAKANE, A ^{[1
]}

YOKOYAMA, Y ^{[1
]}

MURAKAMI, Y ^{[1
]}

机构：

[1] TOHO UNIV, SCH PHARMACEUT SCI, 2-2-1 MIYAMA, FUNABASHI, CHIBA 274, JAPAN

来源：

CHEMICAL & PHARMACEUTICAL BULLETIN | 1994年 / 42卷 / 03期

关键词：

ACYLINDOLE; THALLIUM TRINITRATE; FAVORSKII-TYPE REARRANGEMENT; METHYL ORTHOFORMATE; OXINDOLE; MECHANISM;

D O I：

暂无

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Ethyl acylindole-2-carboxylates were treated with thallium trinitrate (TTN) in methanol, methyl orthoformate, methyl orthoformate/sulfuric acid, and acetic acid. The reactions in the former three methanolic solvents gave methyl indoleacetate derivatives via the Favorskii-type rearrangement reaction at the acyl group, whereas the reaction in acetic acid gave oxindole derivative with rearrangement of the C2-ethoxycarbonyl group. The TTN reaction was applied to a model compound leading to the synthesis of lysergic acid.

引用

页码：443 / 453

页数：11

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