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Synlett 2009(10): 1543-1557  
DOI: 10.1055/s-0029-1217190
ACCOUNT
© Georg Thieme Verlag Stuttgart ˙ New York

Polynitromethanes - Unique Reagents in the Synthesis of Nitro-Substituted Heterocycles

Elena B. Averina, Tamara S. Kuznetsova*, Nikolai S. Zefirov
Department of Chemistry, Lomonosov Moscow State University, Leninskie Gory 1-3, Moscow 119992, Russian Federation
Fax: +7(495)9393969; e-Mail: kuzn@org.chem.msu.ru;
Further Information

Publication History

Received 17 July 2008
Publication Date:
02 June 2009 (online)

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Abstract

The aim of this account is to present the latest findings from studies of the reactions of polynitromethanes with unsaturated compounds and oxiranes, and to review how these processes have been used in the synthesis of highly functionalized nitro compounds and nitrogen- and oxygen-containing heterocycles. In addition, literature on unstable acyclic nitronic esters, key intermediates in the tandem, multicomponent heterocyclization reactions of strained olefins, electrophilic alkenes, acetylenes, and oxiranes, is analyzed.

1 Introduction

2 Reactions of Polynitromethanes with Olefins Bearing Small Rings

3 Three-Component Reactions of Polynitromethanes with Olefins

4 Three-Component Reactions of Halotrinitromethanes with Alkenes

5 Three-Component Reactions of Polynitromethanes with Olefins and Alkynes: Synthesis of gem-Dinitroaziridines and 1,1-Dinitrocyclopropanes

6 Synthesis of 3-Nitroisoxazolines

7 Reactions of Polynitromethanes with Oxiranes

7.1 Two-Component Reactions of Polynitromethanes and ­Oxiranes

7.2 Three-Component Reactions of Polynitromethanes and ­Oxiranes

7.3 Unusual Reactions of Vinyl Ketones with Tetranitro­methane

8 Conclusions

Key words

polynitromethanes - nitronic esters - strained alkenes - three-component reactions - heterocycles

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