Design and synthesis of α-aminonitrile-functionalized novel retinoids

被引：6

作者：

Das, Bhaskar C. ^{[1
,2
]}

Anguiano, Jaime ^{[2
]}

Mahalingam, Sakkarapalayam M. ^{[2
]}

机构：

[1] Albert Einstein Coll Med, Dept Nucl Med, Bronx, NY 10461 USA

[2] Albert Einstein Coll Med, Dept Dev & Mol Biol, Bronx, NY 10461 USA

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 40期

关键词：

Retinoids; alpha-Aminonitrile; Pinacolatoborane; Boron-containing retinoids; ACUTE PROMYELOCYTIC LEUKEMIA; ORGANIC-SYNTHESIS; 3-COMPONENT CONDENSATION; STEREODIRECTED SYNTHESIS; RHABDOID TUMORS; BORONIC ESTERS; AMINO-ACIDS; INDIUM; INHIBITORS; AGENTS;

D O I：

10.1016/j.tetlet.2009.07.119

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have developed an expedient one-pot method for the synthesis of alpha-aminonitrile-functionalized new retinoids via a three-component condensation of beta-cyclocitral, amine, and TMSCN (trimethyl silylcyanide) in the presence of a catalytic amount of indium(III) chloride in water. The reactions proceeded smoothly at room temperature in water to generate the corresponding retinoids in moderate to excellent yields (85-92%). In addition, the utility of this reaction was demonstrated to synthesize boron-containing retinoids. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：5670 / 5672

页数：3

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