Synthesis and Quantum Chemical Studies on the Tautomeric Structures of New Thiazole and Thiadiazine Derivatives

Gomha, Sobhi M.; El‐Hag, Fatma A. A.; Defrawy, Ahmed M. El; Farghaly, Thoraya A.

doi:10.2174/1570179413666160624093735

Cited by 4 publications

(6 citation statements)

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“…3‐Acetyl‐1,5‐diphenyl‐1 H ‐pyrazole‐4‐carbonitrile ( 14 ) reacted with thiocarbohydrazide 95 in ethanol in the presence of HCl and afforded one of the two products 96 or 97 as evidenced by thin‐layer chromatography. This was further supported with the PM6 and PDDG semi‐empirical calculations, where compound 96 was found to be the product that is likely to be obtained as inferred from its lower heat of formation as compared with compound 97 (Scheme ) .…”

Section: Chemistry Of 3‐acetylpyrazolessupporting

confidence: 66%

“…2‐(1‐(4‐Cyano‐1,5‐diphenyl‐1 H ‐pyrazol‐3‐yl)ethylidene)hydrazinecarbothio‐amide ( 85 ) was prepared via condensation of 3‐acetyl‐1,5‐diphenyl‐1 H ‐pyrazole‐4‐carbonitrile ( 14 ) with thiosemicarbazide 83 in the presence of drops of hydrochloric acid (Scheme ) .…”

Section: Chemistry Of 3‐acetylpyrazolesmentioning

confidence: 99%

“…Reaction of ketonic hydrazonoyl chlorides 4a–g with hydrazine carbothioamidederivative 85 afforded one isolable product whose structure is one of the four tautomeric structures 86A–D (Scheme ) . The heat of formation, total energy, HOMO‐LUMO energy gap, and dipole moment of compounds 86 were calculated, and the results revealed that these compounds show ionization energy around 8.4 eV.…”

Section: Chemistry Of 3‐acetylpyrazolesmentioning

confidence: 99%

“…The reaction of hydrazine carbothioamide 84 with dimethyl acetylenedicarboxylate 87 afforded thiazolidinone derivative 89 according to the PM6 calculations (Scheme ) .…”

Section: Chemistry Of 3‐acetylpyrazolesmentioning

confidence: 99%

“…Thiosemicarbazone 84 was considered to be useful synthon for further synthesis of different heterocyclic compounds. Thus, cyclization of 84 with various haloketones such as chloroacetone 91 and phenacyl bromide 92 furnished the thiazole derivatives 93 and 94 , respectively (Scheme ) .…”

Section: Chemistry Of 3‐acetylpyrazolesmentioning

confidence: 99%

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The Chemistry of Acetylpyrazoles and Its Utility in Heterocyclic Synthesis

Abdelhamid

Gomha

2019

Journal of Heterocyclic Chem

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A literature survey revealed that a great deal of interest has been focused on the synthesis of functionalized pyrazole derivatives due to their synthetic and biological potentialities. The pharmacological activities that have been found for some pyrazole derivatives include selective enzyme inhibition, antiviral, estrogen receptor agonist, anti‐inflammatory, anticancer, antiobesity, and antitumor properties. Other activities such as potential inhibitors of HIV‐1, pesticides, fungicides, and antihypertensive agents were reported for other pyrazole derivatives. This review summarizes the synthetic methods and reactions of 3‐acetyl‐pyrazoles, 4‐acetyl‐pyrazoles, and 3,4‐di‐acetyl‐pyrazoles. Most reaction types have been successfully applied and used in the production of biologically active compounds. The aim of this review is to focus mainly on the utility of acetylpyrazole derivatives in the synthesis of heterocyclic compounds during the period 1990–2018.

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Section: Chemistry Of 3‐acetylpyrazolessupporting

confidence: 66%

Section: Chemistry Of 3‐acetylpyrazolesmentioning

confidence: 99%

Section: Chemistry Of 3‐acetylpyrazolesmentioning

confidence: 99%

“…The reaction of hydrazine carbothioamide 84 with dimethyl acetylenedicarboxylate 87 afforded thiazolidinone derivative 89 according to the PM6 calculations (Scheme ) .…”

Section: Chemistry Of 3‐acetylpyrazolesmentioning

confidence: 99%

Section: Chemistry Of 3‐acetylpyrazolesmentioning

confidence: 99%

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