A New Synthesis of Sulfur-, Nitrogen- and Oxygen-Containing Eight-Membered Ring Lactams

被引：18

作者：

Pflantz, Rebekka ^{[1
]}

Sluiter, Jonas ^{[1
]}

Kricka, Mario ^{[1
]}

Saak, Wolfgang ^{[1
]}

Hoenke, Christoph ^{[2
]}

Christoffers, Jens ^{[1
]}

机构：

[1] Carl VonOssietzky 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 | 2009年 / 2009卷 / 31期

关键词：

Lactams; Heterocycles; Sulfur compounds; Medium ring compounds; Ring expansion; Amines; SOLID-PHASE SYNTHESIS; HETEROCYCLIC-COMPOUNDS; PRIMARY AMINES; DERIVATIVES; SYSTEM; BENZODIAZOCINES; 1,4-DIKETONES; EXPANSION; LIBRARIES; PEPTIDES;

D O I：

10.1002/ejoc.200900825

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Bi(NO3)(3)-catalyzed ring expansion of five-membered ring 1,4-diketones in the presence of primary amines leads to eight-membered ring lactams. When applied to starting materials with a tetrahydrothiophene or pyrrolidine moiety, tetrahydro-2H-1,4-thiazocin-3-ones and hexahydro-1,4-diazocin-2-ones are obtained as representatives of these very rare heterocyclic systems. In the case of tetrahydrofuran derivatives, other reaction conditions are required and yields of tetrahydro-2H-1,4-oxazocin-3-ones are very low. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

引用

页码：5431 / 5436

页数：6

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