Efficient Diastereoselective Three-Component Synthesis of Pipecolic Amides

被引：13

作者：

van der Heijden, Gydo ^{[1
]}

van Schaik, Timo B. ^{[1
]}

Mouarrawis, Valentinos ^{[1
]}

de Wit, Martin J. M. ^{[1
]}

Vande Velde, Christophe M. L. ^{[2
]}

Ruijter, Eelco ^{[1
]}

Orru, Romano V. A. ^{[1
]}

机构：

[1] Vrije Univ Amsterdam, Amsterdam Inst Mol Med & Syst, Dept Chem & Pharmaceut Sci, Boelelaan 1108, NL-1081 HZ Amsterdam, Netherlands

[2] Univ Antwerp, Fac Appl Engn, Adv Reactor Technol, Groenenborgerlaan 171, B-2020 Antwerp, Belgium

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 2019卷 / 31-32期

基金：

美国国家科学基金会;

关键词：

Multicomponent reactions; Stereoselectivity; Pipecolic amides; Pharmaceuticals; Argatroban; UGI REACTION; STEREOSELECTIVE-SYNTHESIS; CYCLIC IMINES; ACID; ARGATROBAN; DERIVATIVES; ANALOGS;

D O I：

10.1002/ejoc.201900399

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient Ugi-type three-component reaction (U-3CR) for the synthesis of pipecolic amides is reported. The U-3CR between electronically diverse isocyanides, carboxylic acids and 4-substituted Delta 1-piperideines proceeds in a highly diastereoselective fashion. The Delta 1-piperideines are obtained by NCS-mediated oxidation of the corresponding 4-substituted piperidines, which in turn are generated by an efficient two-step procedure involving the alkylation of 4-picoline and subsequent catalytic hydrogenation of the pyridine ring. We demonstrate the utility of this U-3CR, in combination with the convertible isocyanide 2-bromo-6-isocyanopyridine, in the synthesis of the anticoagulant argatroban.

引用

页码：5313 / 5325

页数：13

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