Rapid syntheses of nitroheterocycles that bear a diethyl methylene-malonate group β to a nitro group

被引：19

作者：

Crozet, MD ^{[1
]}

Perfetti, P ^{[1
]}

Kaafarani, M ^{[1
]}

Crozet, MP ^{[1
]}

Vanelle, P ^{[1
]}

机构：

[1] Univ Mediterranee, Fac Pharm, Lab Chim Organ Pharmaceut, CNRS UMR 6517, F-13385 Marseille 05, France

来源：

LETTERS IN ORGANIC CHEMISTRY | 2004年 / 1卷 / 04期

关键词：

Sulfonyl carbanion; Julia olefination; desulfonylation; S(RN)1; 5-nitroimidazole; 5-nitrothiazole;

D O I：

10.2174/1570178043400488

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Rapid syntheses of nitroheterocycles that bear a diethyl methylenemalonate group beta to a nitro group starting from easily available nitroheterocyclic sulfones and involving, a one-pot substitution-elimination with either diethyl bromomalonate or an original direct olefination with diethyl ketomalonate, gave moderate yields in nitroimidazole series. An S(RN)1 reaction followed by a base-mediated nitrous acid elimination gave fairly good yields in nitrothiazole series. Because of the accessibility of the reagents, these syntheses are interesting alternatives to Knoevenagel reaction.

引用

页码：326 / 330

页数：5

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