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

doi:10.1023/a:1016338226670

Cited by 7 publications

(9 citation statements)

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“…The starting bromoacetyl derivatives 1 and 2 were synthesized as in [7], and the substituted thioureas 3b-3e were synthesized as in [8].…”

Section: Methodsmentioning

confidence: 99%

“…Earlier [7] we reported on a method for obtaining 8-substituted 3-bromoacetyl-3,8-dimethyl-2,7-dioxaspiro [4,4]nonane-1,6-diones 1, 2, containing an active bromoacetyl group, which makes it possible to go on to various heterocyclic compounds of unusual structure. With this aim, we have studied the reaction of compounds 1, 2 with thiourea and arylthioureas under Hansch reaction conditions.…”

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confidence: 99%

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Syntheses based on 8-substituted 3-bromoacetyl-3,8-dimethyl-2,7-dioxaspiro[4,4]nonane-1,6-diones

Kochikyan

Harutyunyan

et al. 2006

Chem Heterocycl Compd

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“…The starting bromoacetyl derivatives 1 and 2 were synthesized as in [7], and the substituted thioureas 3b-3e were synthesized as in [8].…”

Section: Methodsmentioning

confidence: 99%

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confidence: 99%

Syntheses based on 8-substituted 3-bromoacetyl-3,8-dimethyl-2,7-dioxaspiro[4,4]nonane-1,6-diones

Kochikyan

Harutyunyan

et al. 2006

Chem Heterocycl Compd

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“…They are widely used in fine organic synthesis and in synthesis of medicinal agents [1-3]. Therefore, development of new methods of synthesis of oxygen-, nitrogen-, and especially sulfur-containing butano-4-lactone derivatives seems to be a quite important problem, and it could considerably extend the synthetic potential and scope of application of this class of compounds [3][4][5][6][7].We previously showed that the use of alkyl(oxiran-2-ylmethyl)malonic and acetoacetic acid esters [6-9] ensures wide variation of structural fragments in butano-4-lactones and one-step syntheses of various polyfunctionalized butano-4-lactones. Reactions of…”

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confidence: 99%

“…They are widely used in fine organic synthesis and in synthesis of medicinal agents [1][2][3]. Therefore, development of new methods of synthesis of oxygen-, nitrogen-, and especially sulfur-containing butano-4-lactone derivatives seems to be a quite important problem, and it could considerably extend the synthetic potential and scope of application of this class of compounds [3][4][5][6][7].…”

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confidence: 99%

Reactions of aromatic dithiols with diethyl 2-alkyl-2-(oxiran-2-ylmethyl)malonates

2012

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New sulfur-containing butano-4-lactones were synthesized by reaction of diethyl 2-alkyl-2-(oxiran-2-ylmethyl)malonates with biphenyl-4,4′-dithiol, (biphenyl-4,4′-diyl)dimethanethiol, and (2,4,6-trimethylbenzene-1,3-diyl)dimethanethiol. Opening of the oxirane ring in the initial ester followed the Krasuskii rule. † Deceased.Functionally substituted butano-4-lactones constitute a promising class of organic compounds. They are widely used in fine organic synthesis and in synthesis of medicinal agents [1-3]. Therefore, development of new methods of synthesis of oxygen-, nitrogen-, and especially sulfur-containing butano-4-lactone derivatives seems to be a quite important problem, and it could considerably extend the synthetic potential and scope of application of this class of compounds [3][4][5][6][7].We previously showed that the use of alkyl(oxiran-2-ylmethyl)malonic and acetoacetic acid esters [6-9] ensures wide variation of structural fragments in butano-4-lactones and one-step syntheses of various polyfunctionalized butano-4-lactones. Reactions of

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“…In particular, some carboxylactone esters are used as additives to rocket propellants [1], in the synthesis of oxazolines [2], prostaglandins derivatives [3], and triazolyllactones [4][5][6][7][8] exhibiting hypotensive and antitumor action.…”

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Synthesis of 2-substituted aminothiazol-4(5H)-ones proceeding from carboxylactones

2011

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New representatives of 2,2,4-trisubstituted butano-4-lactones were synthesized. By a series of transformations the corresponding γ-carboxylactones were obtained. The latter served as starting compounds for preparation of heteryl-linked lactones, 5-[5-{(alkoxymethyl)-2-oxotetrahydrofuran-3-yl}methyl]-2-arylaminothiazol-4(5Н)-ones.Carboxylactones are known to be successfully used in the synthesis of compounds of various classes. In particular, some carboxylactone esters are used as additives to rocket propellants [1], in the synthesis of oxazolines [2], prostaglandins derivatives [3], and triazolyllactones [4-8] exhibiting hypotensive and antitumor action.The aim of this study was the extension of the choice of carboxylactones, the development of the procedures for the preparation therefrom of new heterocyclic compounds, and the investigation of the useful practical properties of the latter. To fulfi ll this goal we selected as initial compounds ethyl 5-alkoxymethyl-2-oxotetrahydrofuran-3-carboxylates Iа-Ic, being good CH-acids. We carried out the condensation of compounds Iа-Ic with methyl acrylate in the conditions of Michael reaction. As a result we obtained in high yields ethyl 5-(alkoxymethyl)-3-(3-methoxy-3-oxopropyl)-2-oxotetrahydro furan-3-carboxylates IIа-3 ONa O ROH 2 C COOEt O Ia _ Ic O ROH 2 C COOEt O IIa _ IIc CH 2 CH 2 COOCH 3 CH 2 =CHCOOCH 3 O ROH 2 C O IIIa _ IIIc CH 2 CH 2 COOH (2) H + , _ CO 2(1) OH _ IIc which by the alkaline hydrolysis were converted into 3-[5-(alkoxymethyl)-2-oxotetrahydrofuran-3-yl]-propionic acids IIIа-IIIc (Scheme 1). The best results were obtained in the condensation catalyzed with sodium methylate followed by the hydrolysis with 30% solution of NaOH.Taking into consideration that the halo-substituted γ-lactones are successfully used for preparation of compounds of various classes [9, 10], analogs of natural substances [11,12], carboxylactones IIIа-IIIc were converted into the corresponding acyl chlorides IVа-IVc by the treatment with thionyl chloride in the presence of catalytic quantity of DMF (Scheme 2). Further the bromination of compounds IVа-IVc and the subsequent reaction of the obtained chlorides of α-bromoacids with anhydrous ethanol afforded in a high yield ethyl 2-bromo-3-(5-alkoxymethyl 2-oxotetrahydrofuran-3-yl) propanoates Vа-Vc (Scheme 2). Scheme 1. R = C 2 H 5 (a), iso-C 3 H 7 (b), C 5 H 11 (c).

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Cited by 7 publications

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Syntheses based on 8-substituted 3-bromoacetyl-3,8-dimethyl-2,7-dioxaspiro[4,4]nonane-1,6-diones

Syntheses based on 8-substituted 3-bromoacetyl-3,8-dimethyl-2,7-dioxaspiro[4,4]nonane-1,6-diones

Reactions of aromatic dithiols with diethyl 2-alkyl-2-(oxiran-2-ylmethyl)malonates

Synthesis of 2-substituted aminothiazol-4(5H)-ones proceeding from carboxylactones

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