New stereoselective synthesis of 2-allyl-4-nitroalkylpiperidine-2-thiones and their transformation to annulated piperidinones

被引：15

作者：

Sosnicki, JG ^{[1
]}

机构：

[1] Tech Univ Szczecin, Inst Chem & Environm Protect, PL-71065 Szczecin, Poland

来源：

SYNLETT | 2003年 / 11期

关键词：

thiolactams; lactams; nitro compounds; thio-Claisen rearrangement; radical 5-exo-trig annulation;

D O I：

10.1055/s-2003-41016

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Highly stereocontrolled access to trans-3-allyl-4nitro-alkyl-1,6-disubstituted delta-thiolactams was achieved starting from piperidine-2-thione or commercially available 2-mercaptopyridine via Michael-addition of nitroalkanes to 5,6-dihydropyridin-2-thiones, S-allylation and thio-Claisen rearrangement. The corresponding lactams obtained by desulfurisation, were found to be suitable precursors for the construction of trans-fused bicyclic 2-piperidinone derivatives (octahydro[2]pyrindinones) in a regio- and stereoselective radical 5-exo-trig annulation process.

引用

页码：1673 / 1677

页数：5

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