ALDOL CONDENSATION OF N-ALKYLATED-3-ARYL-4,6-DIMETHOXY-7-FORMYLINDOLES AS A GOOD METHOD FOR THE SYNTHESIS OF 1-ARYL-6,8-DIMETHOXYPYRROLO[3,2,1-hi] INDOLE-4-CARBOXYLATES

被引：0

作者：

Jumina ^{[1
]}

机构：

[1] Gadjah Mada Univ, Fac Math & Nat Sci, Dept Chem, Yogyakarta 55281, Indonesia

来源：

INDONESIAN JOURNAL OF CHEMISTRY | 2006年 / 6卷 / 03期

关键词：

indole; pyrroloindole; aldol condensation; alkylation; and formylation;

D O I：

暂无

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Alkylation of 3-aryl-4,6-dimethoxyindole 3a and 3b with methyl and ethyl alpha-bromoacetates afforded good yields of indol-1-ylacetates 4. Treatment of these indoles 4 with the Vilsmeier formylation reagent gave formylindoles 5 in 54-81 % yield. These formylindole 5 underwent intramolecular aldol condensation when treated with sodium hydride in tetrahydrofuran to give pyrroloindole-4-carboxylates 6 in 30-60 % yield. Structural assignment based on spectroscopic data confirmed the structure of the synthesized pyrroloindoles. In the case of pyrroloindole 6c, the structure of this molecule was also proven by X-ray crystallography data.

引用

页码：297 / 303

页数：7

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