Synthesis of polysubstituted 3-thiofurans by regiospecific mono-ipso-substitution and ortho-metallation from 3,4-dibromofuran

被引：30

作者：

AlvarezIbarra, C

Quiroga, ML

Toledano, E

机构：

[1] Depto. de Quim. Orgánica, Facultad de Química, Universidad Complutense, 28040 Madrid, s/n

来源：

TETRAHEDRON | 1996年 / 52卷 / 11期

关键词：

D O I：

10.1016/S0040-4020(96)00069-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthetic potential of 3,4-dibromofuran has been assessed by its conversion into 3,4-disubstituted furans via mono-S-ipso-substitution. The ability of 3-methylthio and 3-phenylthio substituents for directing the metallation at position alpha-relative to the substituent has allowed the regiospecific alkylation. It provides a straightforward approach to several 3-monothiosubstituted furans which are receiving increasing interest as odour and flavour chemicals.

引用

页码：4065 / 4078

页数：14

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