New syntheses on the basis of ethyl 2-oxotetrahydrofuran-3-carboxylates

Kochikyan, T. V.; Arutyunyan, E. V.; Arutyunyan, V. S.; Avetisyan, A. A.

doi:10.1134/s1070428008060122

Cited by 5 publications

(4 citation statements)

References 10 publications

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“…To achieve the goal, starting triazoles with different substituents at the 4-and 5-positions were synthesized from the corresponding acids using a previously reported procedure. [9] To introduce the propyl group at the 4-position of the triazole compound 1 k, compound 1 j was reduced with hydrazine in the presence of air according to a method we had previously developed (Scheme 4). [10a] Compound 1 j was chosen as a model starting compound because it does not contain aromatic groups and allows ready identification of the resulting compounds by NMR analysis.…”

Section: Resultsmentioning

confidence: 99%

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Ligand‐Free Copper(0)‐Catalyzed C−S Ullmann‐Type Cross‐Coupling Reaction: S‐Arylation of 5,4‐Disubstituted 2,4‐Dihydro‐3H‐1,2,4‐triazole‐3‐thiones

Petrosyan,

Ayvazyan,

Ghochikyan

et al. 2024

Eur J Org Chem

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Studied the S‐arylation of 5,4‐disubstituted‐2,4‐dihydro‐3H‐1,2,4‐triazole‐3‐thiones under ligand‐free Cu(0) catalyzed Ullmann‐type reaction conditions. Optimum reaction conditions and the effect of substituents in the arylating agent on the course of the reaction were revealed. The presence of EWG in aryl halides allows the reaction to be carried out without a catalyst, in particular, the presence of EWG in the para position of the aromatic ring has a limiting effect on the leaving group independent of the halogen.

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Section: Resultsmentioning

confidence: 99%

“…To achieve the goal, starting triazoles with different substituents at the 4‐ and 5‐positions were synthesized from the corresponding acids using a previously reported procedure [9] …”

Section: Resultsmentioning

confidence: 99%

Ligand‐Free Copper(0)‐Catalyzed C−S Ullmann‐Type Cross‐Coupling Reaction: S‐Arylation of 5,4‐Disubstituted 2,4‐Dihydro‐3H‐1,2,4‐triazole‐3‐thiones

Petrosyan,

Ayvazyan,

Ghochikyan

et al. 2024

Eur J Org Chem

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“…The melting points were determined on a Boetius melting point apparatus. Initial carboxylic acid hydrazides Ia-Ie were synthesized according to the procedure described in [8].…”

Section: Methodsmentioning

confidence: 99%

Synthesis of 1,2,4-triazole-3-thiols and their S-substituted derivatives

Kochikyan¹,

Samvelyan²,

Arutyunyan³

et al. 2010

Russ J Org Chem

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New 1,2,4-triazole-3-thiols were synthesized by reactions of the corresponding carboxylic acid hydrazides with isothiocyanates and subsequent cyclization of intermediate 1,4-substituted thiosemicarbazides. Alkylation of 1,2,4-triazole-3-thiols with benzyl chlorides and bromacetophenones gave only S-substituted derivatives. † Deceased.Biological studies on synthetic analogs of naturally occurring heterocyclic compounds showed that most of them exhibit a broad spectrum of biological activity. Among compounds of this series, of particular interest are 1,2,4-triazoles which are mostly of synthetic origin. Some 1,2,4-triazole derivatives exhibit hypotensive effect [1] and possess antitumor [2], fungicidal [3], antibacterial [4], and other kinds of biological activity.While searching for new useful properties in the series of 1,2,4-triazoles we synthesized their new derivatives. Reactions of carboxylic acid hydrazides Ia-Id with allyl, phenyl, and furfurylmethyl isothiocyanates gave 1,4-disubstituted thiosemicarbazides IIa-IIe. Optimal conditions for this reaction were found. The best results were obtained by heating the initial reactants in ethanol for a short time [5]. Compounds IIa-IIe underwent intramolecular cyclization in alkaline medium to form targeted 3,4-disubstituted 1,2,4-triazole-3-thiols IIIa-IIIe. It is advisable to carry out this reaction with the use of 10% aqueous sodium or potassium hydroxide. The cyclization was complete in 4 h, and compounds IIIa-IIIe were formed in high yield [6] (Scheme 1).From the viewpoint of biological activity, synthesis of 1,2,4-triazole-3-thiol derivatives substituted at the sulfur atom seemed to be promising. For instance, biological effects of compounds possessing free and substituted thiol groups could be compared. 3,4-Disubstituted 1,2,4-triazole-3-thiols IIIa-IIIe were subjected to alkylation with various halogen derivatives, specifically with substituted benzyl chlorides and bromoacetophenones (Scheme 2). The optimal conditions for the alkylation with benzyl chlorides included the use of anhydrous acetone as solvent and anhydrous potassium carbonate as base and prolonged heating (10 h). The reactions of III with bromoacetophenones were complete in 2 h in the absence of a base.

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“…13 C NMR (CDCl 3 , 100 MHz) δ (ppm): 173.5, 155.5, 67.5, 54.3, 51.2, 33.5, 28.1, 25.0, 24.2. Mass spectrum, m/z: 190 204 ([M] + , <1%), 173 (7), 131 (8), 128 (39), 113 (22), 100 (14), 99 (9), 97 (39), 96 (27), 87 (36), 85 (6), 77 (20), 74 (92), 69 (86), 68 (100), 67 (18), 59 (72), 57 (8), 56 (8), 55 (83), 54 (8), 45 (30), 43 (28), 42 (20), 41 (57), 39 (20).…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Upgrading of Biobased Lactones with Dialkylcarbonates

Caretto

Noè

Selva

et al. 2014

ACS Sustainable Chem. Eng.

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Four renewable lactones, γ-butyrolactone, γ-valerolactone, δ-valerolactone, and ε-caprolactone (GBL, GVL, DVL, ECL, respectively) were shown to react with dimethyl-, diethyl-, and dibenzyl-carbonate (DMC, DEC, DBnC, respectively) in the presence of K2CO3 as basic catalyst, to yield selectively either the α-alkyl derivatives 1c–6c in the case of the five-membered ring GBL and GVL or the highly oxygenated acyclic monomeric derivatives 7a, 8a, and 9a in the case of the six- and seven-membered rings DVL and ECL. Selectivity and reaction conditions are investigated and a reaction mechanism is proposed. The organic carbonates act both as reagent and as reaction solvents, and the catalyst can be recovered by filtration and recycled

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New syntheses on the basis of ethyl 2-oxotetrahydrofuran-3-carboxylates

Cited by 5 publications

References 10 publications

Ligand‐Free Copper(0)‐Catalyzed C−S Ullmann‐Type Cross‐Coupling Reaction: S‐Arylation of 5,4‐Disubstituted 2,4‐Dihydro‐3H‐1,2,4‐triazole‐3‐thiones

Ligand‐Free Copper(0)‐Catalyzed C−S Ullmann‐Type Cross‐Coupling Reaction: S‐Arylation of 5,4‐Disubstituted 2,4‐Dihydro‐3H‐1,2,4‐triazole‐3‐thiones

Synthesis of 1,2,4-triazole-3-thiols and their S-substituted derivatives

Upgrading of Biobased Lactones with Dialkylcarbonates

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