Solution-phase synthesis of a combinatorial thiohydantoin library

被引：71

作者：

Sim, MM ^{[1
]}

Ganesan, A ^{[1
]}

机构：

[1] NATL UNIV SINGAPORE,INST MOL & CELL BIOL,SINGAPORE 119260,SINGAPORE

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1997年 / 62卷 / 10期

关键词：

D O I：

10.1021/jo962376u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient one-pot three-component synthesis of thiohydantoins was developed. In the first step, amino acid esters were alkylated by imine formation with aldehydes and reduction by sodium triacetoxyborohydride. In the second step, an isothiocyanate was added together with a molar equivalent of triethylamine, leading to the thiohydantoin product in high yield and purity after an extractive aqueous workup. This procedure was used to generate a combinatorial library of over 600 discrete thiohydantoins on a 0.1 mmol scale. Sampling of 10% of this library showed the thiohydantoin to be the major product in all cases, with purities of 52-98% by HPLC analysis. The cyclization conditions can also be adapted to the synthesis of hydantoins.

引用

页码：3230 / 3235

页数：6

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