Conjugate Addition versus Cycloaddition/Condensation of Nitro Compounds in Water: Selectivity, Acid-Base Catalysis, and Induction Period

被引：27

作者：

Guideri, Luca ^{[1
]}

De Sarlo, Francesco ^{[1
]}

Machetti, Fabrizio ^{[1
]}

机构：

[1] Univ Florence, Dipartimento Chim Ugo Schiff, Ist Chim Composti Organometall, Consiglio Nazl Ric, I-50019 Florence, Italy

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2013年 / 19卷 / 02期

关键词：

cycloaddition; homogeneous catalysis; Michael addition; nitrogen heterocycles; water; DIRECT MICHAEL ADDITION; DIELS-ALDER REACTIONS; ISOXAZOLINE DERIVATIVES; PRIMARY NITROALKANES; COUPLING REACTIONS; ORGANIC-REACTIONS; MEYER REACTION; IONIC LIQUIDS; EFFICIENT; KINETICS;

D O I：

10.1002/chem.201202698

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Nitroacetates and nitroacetamides react in water as in chloroform with electron-deficient dipolarophiles to give condensation or conjugate addition products under base catalysis. In general, high selectivity towards condensation is observed in water, with shorter induction periods than in chloroform. In water, condensations slowly occur even without base; kinetic profiles evidence the catalytic effect of the base, which should be related to the conversion into the tautomer nitronic acid. Condensations in water provide convenient access to isoxazole derivatives bearing various functional groups including ammonium, carboxy, and carboxyamide.

引用

页码：665 / 677

页数：13

共 134 条

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