Investigation of the selective reduction of isatin derivatives.: Synthesis of α-hydroxyacetophenone derivatives and ethyl spiro-3,3-(ethylenedioxy)-2-hydroxyindoline carboxylates

被引：9

作者：

Garden, SJ ^{[1
]}

Côrrea, MB ^{[1
]}

Pinto, AC ^{[1
]}

机构：

[1] Univ Fed Rio de Janeiro, Dept Quim Organ, BR-21945970 Rio De Janeiro, Brazil

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 41期

关键词：

hydroxylactam; alpha-hydroxyacetophenone; isatin; reduction; N-acyliminium precursor;

D O I：

10.1016/j.tetlet.2003.08.058

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The product from the reduction of ethyl spiro-3,3-(ethylenedioxy)-2-oxindole carboxylates (1) using borohydride salts has been found to be dependant upon both solvent and metal ion. With polar solvents and lithium bromide/sodium borohydride, spiro-3,3-(ethylenedioxy)-2-hydroxyindole carboxylates (2) are obtained in high yields whilst [2-(2-hydroxymethyl-[1,3]dioxolan-2-yl)-phenyl]-carbamic acid ethyl esters (3) are obtained using sodium borohydride in less polar solvents. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：7617 / 7621

页数：5

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