Synthesis of Triazolyl-Substituted 3-Aminopiperidines by Huisgen-1,3-Dipolar Cycloaddition - New Scaffolds for Combinatorial Chemistry

被引：19

作者：

Schramm, Heiko ^{[1
]}

Saak, Wolfgang ^{[1
]}

Hoenke, Christoph ^{[2
]}

Christoffers, Jens ^{[1
]}

机构：

[1] Carl von Ossietzky Univ Oldenburg, Inst Reine & Angew Chem, D-26111 Oldenburg, Germany

[2] Boehringer Ingelheim Pharma GmbH & Co KG, Abt Chem Forsch, D-88397 Biberach, Germany

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 2010卷 / 09期

关键词：

Nitrogen heterocycles; Cycloaddition; Click reaction; Amines; STEREOSELECTIVE-SYNTHESIS; CLICK CHEMISTRY; PIPERIDINE; AZIRIDINES; EPOXIDES;

D O I：

10.1002/ejoc.200901458

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Orthogonally N-protected (Boc and Cbz) 4-(1,2,3-triazol-4-yl)-substituted 3-aminopiperidines are new scaffolds for combinatorial chemistry. They were prepared from a piperidine building block by a sequence of nucleophilic aziridine ring opening with NaN3 and subsequent copper-catalyzed Huisgen 1,3-dipolar cycloaddition with ten different alkynes. Constitution and relative configuration of the major as well as minor products were established by single-crystal X-ray structure analysis of bromophenylsulfonyl derivatives.

引用

页码：1745 / 1753

页数：9

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