Novel applications of carbon dioxide/MeOH for the synthesis of hydantoins and cyclic ureas via the Ugi reaction

被引：74

作者：

Hulme, C ^{[1
]}

Ma, L ^{[1
]}

Romano, JJ ^{[1
]}

Morton, G ^{[1
]}

Tang, SY ^{[1
]}

Cherrier, MP ^{[1
]}

Choi, S ^{[1
]}

Salvino, J ^{[1
]}

Labaudiniere, R ^{[1
]}

机构：

[1] Rhone Poulenc Rorer Cent Res, New Leads Discovery, Collegeville, PA 19426 USA

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 12期

关键词：

D O I：

10.1016/S0040-4039(00)00053-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This communication reveals novel applications of the CO2/MeOH reagent combination coupled with the UDC (Ugi/DeBOC/Cyclize) strategy. The Ugi five component condensation (5CC) affords carbamate protected amino-amides in good yield. When one of the supporting reagents employed in the Ugi reaction possesses a tethered amino-BOC protected functional group, subsequent acid treatment and proton scavenging results in rapid cyclization to cyclic ureas. Additionally, treatment of the 5CC product with base affords hydantoins in good yield, representing a novel and short approach to this class of molecule. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：1889 / 1893

页数：5

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