4,5-Dihydro-1,2,4-triazin-6(1H)-ones (microreview)

Kowalczyk, Anna; Jasiński, Marcin

doi:10.1007/s10593-022-03138-y

Cited by 3 publications

(1 citation statement)

References 24 publications

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“…Information on the use of bis‐ [15] or monohydrazonoyl halides is described in reviews summarizing the results of studies using these halides. Fragmentary references to the use of some representatives of this series in synthetic schemes can also be found in individual chapters of collections, [16] thematic reviews [17–21] or microreviews [22–24] devoted to the analysis of problems in the preparation of other heterocycles, as well as in articles where the results of synthetic work are presented [25]…”

Section: Introductionmentioning

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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Section: Introductionmentioning

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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A new synthetic route towards multifunctionalized cyclic amidrazones for feeding chemical space

Leblanc,

Boutin,

Vega

et al. 2024

Org. Biomol. Chem.

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Trifluoromethylated 4,5-Dihydro-1,2,4-triazin-6(1H)-ones via (3+3)-Annulation of Nitrile Imines with α-Amino Esters

et al. 2023

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The synthesis of two series of monocyclic and bicyclic trifluoromethylated 4,5-dihydro-1,2,4-triazin-6(1H)-one derivatives based on (3+3)-annulation of methyl esters derived from natural α-amino acids with in situ generated trifluoroacetonitrile imines has been described. The devised protocol is characterized by a wide scope, easily accessible substrates, remarkable functional group tolerance, and high chemical yield. In reactions with chiral starting materials, no racemization at the stereogenic centers was observed and the respective enantiomerically pure products were obtained. Selected functional group interconversions carried out under catalytic hydrogenation and mild PTC oxidation conditions were also demonstrated.

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4,5-Dihydro-1,2,4-triazin-6(1H)-ones (microreview)

Cited by 3 publications

References 24 publications

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

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

A new synthetic route towards multifunctionalized cyclic amidrazones for feeding chemical space

Trifluoromethylated 4,5-Dihydro-1,2,4-triazin-6(1H)-ones via (3+3)-Annulation of Nitrile Imines with α-Amino Esters

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