Novel applications of convertible isonitriles for the synthesis of mono and bicyclic γ-lactams via a UDC strategy

被引：63

作者：

Hulme, C ^{[1
]}

Ma, L ^{[1
]}

Cherrier, MP ^{[1
]}

Romano, JJ ^{[1
]}

Morton, G ^{[1
]}

Duquenne, C ^{[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)00052-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This communication reveals a novel application of the so-called convertible isonitriles for the solution/solid phase generation of gamma-lactam analogues. Use of tethered N-BOC aldehydes in the Ugi multi-component reaction (MCR), followed by BOC removal and base treatment (a '3-step, 1-pot procedure') affords gamma-lactams in good yield. The UDC (Ugi/De-BOC/Cyclize) strategy, coupled with a convertible isonitrile, is now feasible from all three substitution sites of the Ugi product. A conceptually novel approach, combining a bi-functional precursor with a post-condensation modification to give fused lactam-ketopiperazines, is also revealed. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：1883 / 1887

页数：5

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