Synthesis-and-properties-of-hydrazones-bearing-amide-thioamide-a-2010.pdf

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Special Issue Reviews and AccountsARKIVOC 2010 (i)275-332ISSN 1551-7012Page275©ARKAT USA, Inc.Synthesis and properties of hydrazones bearing amide, thioamideand amidinefunctionsNataliya P. Belskaya,aWim Dehaen,band Vasiliy A. Bakuleva*aTheUrals State Technical University, 620002, Ekaterinburg, RussiabDepartment of Chemistry, K.U. Leuven, Celestijnenlaan 200F, B-3001 Leuven, BelgiumE-mail:[email protected]AbstractThis review provides detailed methods for the synthesis, structures and chemical properties ofhydrazones bearing carboxamide, thioamide and amidine functions. The main accent was put onthe cyclization reactions leading to pyrazoles, thiazoles, 1,2,3-triazoles, 1,2,3-thiadiazoles, 1,2,4-triazines and other heterocyclic compounds. In addition, we have reviewed methods for thesynthesis of substrates for pericyclic reactions from the hydrazones.Keywords:Hydrazone,carboxamide, thioamide, amidines,сyclizationTable of Contents1. Introduction2. Syntheses of hydrazono-amides, -thioamides and -amidines2.1 Condensation reaction of hydrazines with carbonyl compounds2.2 Coupling of diazonium salts with active methylene compounds2.3 Synthesis of hydrazones by modification of the substituents3. Structure of hydrazono-amides, -thioamides and -amidines3.1 Hydrazono-amides3.2 Hydrazono-thioamides3.3 Hydrazono-amidines4. Chemical properties of hydrazono-amides, -thioamides and -amidines4.1 Reactions with nucleophiles4.2 Reactions with electrophiles4.3 Oxidation and reduction4.4 Use of hydrazono-amides, -thioamides and -amidines in the synthesis of heterocycliccompounds
Special Issue Reviews and AccountsARKIVOC 2010 (i)275-332ISSN 1551-7012Page276©ARKAT USA, Inc.4.4.1 Reactions with derivatives of formic acid, ketones, carbon disulfide andthiophosgene4.4.2 Reactions withα-halocarbonyl compounds4.4.3 Reactions with acetylenecarboxylic esters4.4.4 Reactions with reagents containing electrophilic and nucleophilic functions4.4.5 Intramolecular cyclization reactions4.4.6 Cyclоaddition reactions4.4.7. Oxidative cyclization reactions5. Hydrazono-thioamides for the synthesis of substrates for pericyclic transformationsConclusionsAcknowledgementsReferencesIntroductionHydrazones and their derivatives constitute a versatile class of compounds in organic chemistry.These compounds have interesting biological properties, such as anti-inflammatory, analgesic,anticonvulsant, antituberculous, antitumor, anti-HIV and antimicrobial activity.1Hydrazones areimportant compounds for drug design, as possible ligands for metal complexes, organocatalysisand also for the syntheses of heterocyclic compounds.2The ease of preparation, increasedhydrolytic stability relative to imines, and tendency toward crystallinity are all desirablecharacteristics of hydrazones. Due to these positive traits, hydrazones have been under study fora long time, but much of their basic chemistry remains unexplored.

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Term
Spring
Professor
DorianGray
Tags
Hydrogen Bond, Amide, Organic reaction, Nuclear magnetic resonance, ISSN, ARKAT USA

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