Preparation of 2,3-dihydroselenolo[2,3-b]pyridines and related compounds by free-radical means

被引：12

作者：

Fenner, T ^{[1
]}

White, JM

Schiesser, CH

机构：

[1] Univ Melbourne, Sch Chem, Parkville, Vic 3010, Australia

[2] Univ Melbourne, Mol Sci & Biotechnol Inst Bio21, Parkville, Vic 3010, Australia

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2006年 / 4卷 / 03期

关键词：

D O I：

10.1039/b515385a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Photolysis of the thiohydroximate ester derivative 21 of 2-carboethoxy-2-(2-(benzylseleno)pyridin-3-yl)tridecylcarboxylic acid (20) affords 2-dodecyl-2-carboethoxy-2,3-dihydroselenolo[2,3-b]pyridine (22) in 89% yield in a process presumably involving intramolecular homolytic substitution by a tertiary alkyl radical at selenium with loss of a benzyl radical. Alternatively, rearrangement of O-(co-haloalkyl)esters 34 of 2-carboethoxy-N-hydroxypyridine-2-selone affords azonianaphthalenium halides 37 in 79% yield.

引用

页码：466 / 474

页数：9

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