Facile synthesis of new (Z)-6-arylmethylidene-1,3,4-thiadiazin-5(6H)-one derivatives

Metwally, Nadia H.; Abdelrazek, Fathy M.; Jaeger, Anne

doi:10.1007/s10593-013-1195-3

Cited by 5 publications

(3 citation statements)

References 21 publications

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“…In the last two decades, we have been involved in a program aiming to develop new simple procedures for the preparation of some new heterocyclic compounds of biological interest from laboratory available cheap starting materials .…”

Section: Introductionmentioning

confidence: 99%

3‐(3,5‐Dimethyl‐1H‐Pyrazol‐1‐yl)‐3‐Oxopropanenitrile as Precursor for Some New Mono‐Heterocyclic and Bis‐Heterocyclic Compounds

Metwally

Abdelrazek

Eldaly

et al. 2015

Journal of Heterocyclic Chem

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3‐(3,5‐Dimethyl‐1 H ‐pyrazol‐1‐yl)‐3‐oxopropanenitrile 1 was used as a cyanoacetylating agent for synthesis of the acetanilide derivative 3. Compound 3 was utilized as a key intermediate for the synthesis of some new mono‐chromene and di‐chromene derivatives 9 and 13, the dihydrazo derivatives 15, and the dithiazole derivatives 18 via the condensation with o‐hydroxybenzaldehyde derivatives, the coupling with aryl diazonium salts, or the reaction with phenyl isothiocyanate in presence of KOH followed by phenacyl bromide derivatives respectively.

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Section: Introductionmentioning

confidence: 99%

3‐(3,5‐Dimethyl‐1H‐Pyrazol‐1‐yl)‐3‐Oxopropanenitrile as Precursor for Some New Mono‐Heterocyclic and Bis‐Heterocyclic Compounds

Metwally

Abdelrazek

Eldaly

et al. 2015

Journal of Heterocyclic Chem

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“…The reaction of 3‐aryl‐2‐sulfanylpropenoic acid 30 with acetohydrazonoyl chlorides 31 in boiling EtOH in the presence of an equimolar amount of Et 3 N results in the formation of 1,3,4‐thiadiazinones 32 in satisfactory yields ( Scheme 12). [59] …”

Section: Hydrazonoyl Halides In the Synthesis Of Six‐ And Seven‐membe...mentioning

confidence: 99%

“…The reaction of 3-aryl-2-sulfanylpropenoic acid 30 with acetohydrazonoyl chlorides 31 in boiling EtOH in the presence of an equimolar amount of Et 3 N results in the formation of 1,3,4-thiadiazinones 32 in satisfactory yields (Scheme 12). [59] Upon (3 + 3)-cycloaddition of nitrilimines generated from hydrazonoyl bromides 33 to the decomposition product of 1,4-dithianediol 34, thiadiazinols 35 are formed. Intermediate products A, formed during tosylation of heterocycles 35, are unstable and at room temperature are converted into pyrazoles 36 (Scheme 13 ).…”

Section: Syntheses Of Oxa-and Thiadiazines Involving Hydrazonoyl Halidesmentioning

confidence: 99%

Advances in the Synthesis of Heterocycles with Two and Three Heteroatoms using Hydrazonoyl Halides

Yamaletdinova,

Gataullin

2024

Helvetica Chimica Acta

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The review covers the results of studies published in the literature on the use of hydrazonoyl halides in the synthesis of five‐ (pyrazoles, thiazoles, triazoles, oxa‐ and thiadiazoles), six‐ (oxa‐ and thiadiazines, indazoles, pyridazines, pyrazines, tetrazines) or seven‐membered (benzotriazepine) heterocycles. In the formation of these heterocycles, the main intermediate stage of the reaction is the in situ generation of nitrilimine, which enters into a cycloaddition reaction with substituted acetylenes (including in situ generated benzynes, naphthynes), allenes, activated olefins, anthranilic acid derivatives, organosulfur compounds (mercaptoaldehydes, mercaptocarboxylic acids ) or with fused heterocycles. Examples are given of the formation of heterocycles by replacing the halogen atom from a hydrazonoyl halide molecule with a nucleophilic group, followed by exhaustive intramolecular cyclization into the target compound. There are discussions of reactions in which the cycloaddition of the nitrilimine to the in situ synthesized Knoevenagel condensation product (from CH‐acid compounds, such as di‐ and monocarbonyl compounds, dinitrile malonic acid) occurs, leading to spiro‐linked or conventional pyrazoles. Some syntheses of biologically active representatives are shown.

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ChemInform Abstract: Facile Synthesis of New (Z)‐6‐Arylmethylidene‐1,3,4‐thiadiazin‐5(6H)‐one Derivatives.

2013

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Facile synthesis of new (Z)-6-arylmethylidene-1,3,4-thiadiazin-5(6H)-one derivatives

Cited by 5 publications

References 21 publications

3‐(3,5‐Dimethyl‐1H‐Pyrazol‐1‐yl)‐3‐Oxopropanenitrile as Precursor for Some New Mono‐Heterocyclic and Bis‐Heterocyclic Compounds

3‐(3,5‐Dimethyl‐1H‐Pyrazol‐1‐yl)‐3‐Oxopropanenitrile as Precursor for Some New Mono‐Heterocyclic and Bis‐Heterocyclic Compounds

Advances in the Synthesis of Heterocycles with Two and Three Heteroatoms using Hydrazonoyl Halides

ChemInform Abstract: Facile Synthesis of New (Z)‐6‐Arylmethylidene‐1,3,4‐thiadiazin‐5(6H)‐one Derivatives.

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