Synthesis of 3,4‐Dialkyl‐5‐(1‐oxo‐ethyl)‐3<i>H</i>‐thiazole‐2‐thiones Derivatives and Their Pesticidal Activity

Eliazyan, K. A.; Knyazyan, Aram M.; Pivazyan, V. A.; Ghazaryan, Emma A.; Harutyunyan, Siranush V.; Yengoyan, Aleksandr P.

doi:10.1002/jhet.1596

Cited by 4 publications

(5 citation statements)

References 17 publications

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“…To introduce some pharmacophore groups into molecule structure, some transformations due to the ketone In accordance with literature data some heterocyclic substituted oximes and their ethers show fungicidal [47][48][49], herbicidal [50,51], insecticidal [52], and growth stimulant [49] activities. Therefore, by reaction of ketone (3) with hydroxylamine hydrochloride, the corresponding 2-(1-(hydroxyimino)ethyl)-3,7-dimethyl-5H-thiazolo[3,2-a]pyrimidin-5-one (4d) was synthesized.…”

Section: Resultsmentioning

confidence: 59%

Synthesis and Growth Stimulant Properties of 2-Acetyl-3,7-dimethyl-5H-thiazolo[3,2-a]pyrimidin-5-one Derivatives

Pivazyan

Ghazaryan

Shainova

et al. 2017

Journal of Chemistry

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A convenient, accessible, and high yield method for preparing of 6-methyl-2-thioxo-2,3-dihydropyrimidin-4(1H)-one (1) by treatment of acetoacetic acid ethyl ester with thiourea in sodium methylate was developed. The alkylation of the latter with 3-chloro-pentane-2,4-dione and further regioselective cyclization of intermediate compound (2) in high yield afforded 2-acetyl-3,7-dimethyl-5H-thiazolo[3,2-a]pyrimidin-5-one (3). The halogenation and some transformations of synthesized thiazolo[3,2-a]pyrimidine (3) due to its ketone group were carried out to obtain the corresponding carboxamide, carbothioamide, sulfonohydrazide, and oxime and its alkylated derivatives (5). At preliminary biological studies the synthesized compounds have shown growth stimulant properties. The activity of four of them was higher than 70%, compared with heteroauxin.

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Section: Resultsmentioning

confidence: 59%

Synthesis and Growth Stimulant Properties of 2-Acetyl-3,7-dimethyl-5H-thiazolo[3,2-a]pyrimidin-5-one Derivatives

Pivazyan

Ghazaryan

Shainova

et al. 2017

Journal of Chemistry

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“…NMR spectra were recorded with a spectrometer operating at a field of 14.4 T (600 MHz for 1 H NMR and 150.8 MHz for 13 C NMR). High temperature 1 H NMR spectra were acquired without spinning using a 5 mm dual direct probe with a 9000 Hz sweep width, 3.0 µs (30°tip angle) pulse width, 3 s acquisition time and 1 s delay time.…”

Section: Methodsmentioning

confidence: 99%

“…1) and its derivatives are five membered heterocycles endowed with a wide range of biological activities. 7 For instance, they display many biological activities such as antimicrobial, 8 antimalarial, 9 anti-inflammatory, 10 anticancer, 11 antiviral, 12 pesticidal, 13 and inhibition of HIV-1, 14 gp41, 15 JSP-1, 16 IKKβ, 17 PRL-3, 18 cholesterol esterase, 19 and potential BACE-1. 20 Furthermore, 3-phenylthiazole-2(3H)-thiones act as COX-2 inhibitors, 21 tyrosinase inhibitors 22 and combretastatin analogs.…”

Section: Introductionmentioning

confidence: 99%

Atropisomerism in 3-arylthiazolidine-2-thiones. A combined dynamic NMR and dynamic HPLC study

et al. 2016

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Sterically hindered 3-arylthiazolidine-2-thiones were prepared by a solvent-free reaction with arylisothiocyanates and 1,4-dithiane-2,5-diol. Atropisomerism was observed in two compounds (3 and 4, aryl = 1-naphthyl and 2-methylnaphth-1-yl), whose rotational energy barriers were measured using dynamic NMR and dynamic HPLC. The experimental analyses were supported by DFT calculations. Thermally stable atropisomers were obtained by dehydration of compounds 3 and 4 and the absolute configuration of the atropisomers of compound 6 was determined by theoretical simulation of the ECD and VCD spectra.

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“…In this reaction, new C−S and C−N bond formation takes place. Thiazole‐2(3H)‐thiones and their derivatives are used as bioactive agents, including fungicides, [28] nematicides, [29] and antimicrobial compounds [30] . This method overcomes the drawbacks of previous approaches involving foul‐smelling carbon disulfide, [31] complex reagents, and longer reaction times to access these molecules.…”

Section: Thermal Reactions Of α‐Azidochalconesmentioning

confidence: 99%

Recent Advances in the Use of α‐Azidochalcones in Heterocycle Synthesis

Devi Newar,

Jyoti Boruah,

Awatar Maurya

2024

Adv Synth Catal

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α‐Azidochalcones have emerged as remarkably versatile precursors within organic azides, showcasing a broad spectrum of reactivity as a cornerstone for synthesizing diverse molecular scaffolds. The ongoing progress in this field has opened new opportunities for constructing complex organic molecules through diverse chemical transformations due to the versatile reactivity of α‐azidochalcones for further functionalization. The comprehensive review presented herein provides a concise yet detailed examination of the synthesis, reactivity, and potential applications of α‐azidochalcones. Focusing on both thermal and photochemical pathways, this review highlights the versatility of α‐azidochalcones as pivotal precursors in the synthesis of various heterocyclic frameworks.

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Synthesis of 3,4‐Dialkyl‐5‐(1‐oxo‐ethyl)‐3H‐thiazole‐2‐thiones Derivatives and Their Pesticidal Activity

Cited by 4 publications

References 17 publications

Synthesis and Growth Stimulant Properties of 2-Acetyl-3,7-dimethyl-5H-thiazolo[3,2-a]pyrimidin-5-one Derivatives

Synthesis and Growth Stimulant Properties of 2-Acetyl-3,7-dimethyl-5H-thiazolo[3,2-a]pyrimidin-5-one Derivatives

Atropisomerism in 3-arylthiazolidine-2-thiones. A combined dynamic NMR and dynamic HPLC study

Recent Advances in the Use of α‐Azidochalcones in Heterocycle Synthesis

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