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Synthesis 2008(1): 1-25  
DOI: 10.1055/s-2007-990942
REVIEW
© Georg Thieme Verlag Stuttgart · New York

Multicomponent Reactions of Carbonyl Compounds and Derivatives of Cyanoacetic Acid: Synthesis of Carbo- and Heterocycles

Anatoliy M. Shestopalov*a, Alexander A. Shestopalovb, Lyudmila A. Rodinovskayaa
a N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russian Federation
b Department of Chemistry, Duke University, Durham, NC 27708-0346, USA
e-Mail: shchem@dol.ru.;
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Publication History

Received 6 July 2007
Publication Date:
07 December 2007 (online)

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Abstract

We present herein a review of multicomponent reactions of carbonyl compounds with derivatives of cyanoacetic acid, and denote their differences from other well-known multicomponent reactions. Although this class of multicomponent reactions is widely used in organic chemistry for the synthesis of carbo- and heterocycles, it has not yet been reviewed in a separate publication. This review includes available information on the synthesis of carbocycles (substituted cyclopropanes, spiro-conjugated cyclopropanes, five- and six-membered carbocycles), five-membered heterocycles (furans, thiophenes, pyrroles, thiazoles, and others), and six-membered heterocycles (pyrans, thiopyrans, and pyridines) using the multicomponent reaction of carbonyl compounds with derivatives of cyanoacetic acid.

1 Introduction

2 Multicomponent Carbocyclic Synthesis

2.1 Synthesis of Cyclopropanes

2.2 Synthesis of Five- and Six-Membered Carbocycles

3 Multicomponent Heterocyclic Synthesis

3.1 Synthesis of Five-Membered Heterocycles

3.2 Synthesis of Six-Membered Heterocycles

4 Conclusion

Key words

multicomponent reactions - cyanoacetic acid derivatives - malononitrile - cyanothioacetamide