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DOI: 10.1055/s-0029-1218518
Chemistry of 2-Arylhydrazonals
Publication History
Publication Date:
27 November 2009 (online)
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Abstract
Approaches for the preparation of 2-arylhydrazonals as well as the chemical reactivity profiles and structures of these substances are reviewed. Emphasis is given to the use of these substances in the synthesis of five- and six-membered heterocycles.
1 Introduction
2 Synthetic Approaches to 2-Arylhydrazonals
2.1 Synthesis via Coupling of Enamines with Aromatic Diazonium Salts
2.2 Coupling Reactions of Active Methylenes with Aromatic Diazonium Salts
2.3 Synthesis of Arylhydrazonals via Condensation Reactions with Phenylhydrazine
2.4 Synthesis of Arylhydrazonals via Oxidation of Methyl and Hydroxymethyl Arylhydrazones
3 Structural Investigations
4 Reactions of Arylhydrazonals
4.1 Reactions Involving the Aldehyde Group
4.1.1 Formation of Formazans
4.1.2 Condensation Reactions with Amines, Hydrazines and
Hydroxylamine
4.1.3 Condensation Reactions with Active Methylene Compounds
4.2 Reactions Resulting in the Formation of Heterocycles
4.2.1 Formation of Hydrazononitriles and 1,2,3-Triazoles
4.2.2 Synthesis of Pyrazoles and Fused Pyrazoles
4.2.3 Synthesis of Pyridazines and Fused Pyridazines
4.2.4 Miscellaneous
5 Conclusion
Key words
arylhydrazonals - synthesis - reactivity
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