Cycloaddition reactions of polyfluoroalkylthioncarboxylic acid derivatives with dimethyl acetylenedicarboxylate (DMAD)

“…The reactions of DMAD with thioamides 3 containing polyfluoroalkyl substituents [11,24] differ from the cycloacylation of the unfluorinated substrates. On account of the strong electron-withdrawing effect of the polyfluoroalkyl groups 2-methoxy-2-R-5-methoxycarbonylmethylenethiazolidin-4-ones 4 and not thiazolidin-4-ones are formed in this reaction.…”

Section: Reactions With Acetylenedicarboxylic Estermentioning

confidence: 99%

“…Therefore, in spite of the fact that the first papers on this subject were published 50 of more years ago [7,8] synthetic investigations in the field are continuing to this day [9][10][11][12].…”

mentioning

confidence: 99%

Cycloacylation of thioamides and their derivatives by compounds containing an activated multiple bond (review)

Britsun

Lozinskii

2007

Chem Heterocycl Comp

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The cycloacylation reactions of thioamides and their derivatives containing an activated multiple bond are analyzed and summarized.The cycloacylation of thioamides and their derivatives containing an activated multiple bond is an accessible and convenient method for the synthesis of five-and six-membered sulfur-and nitrogen-containing heterocycles -primarily 4H-1,3-thiazin-4-ones [1] and thiazolidin-4-ones [2], and also 2-thioxopiperidines [3], thiopyran-4-ones [4], and pyrimidin-4-ones [5]. Heterocyclic compounds of these types exhibit a wide spectrum of biological activity and have extensive practical applications [1,2,6].This group of reactions is also of interest from the theoretical standpoint since they make it possible to study, analyze, and predict the relationships between the reactivity of substrates containing the ambident NH─C═S group and their structure, reaction conditions, and the nature of substituents at the heteroatoms. Therefore, in spite of the fact that the first papers on this subject were published 50 of more years ago [7,8] synthetic investigations in the field are continuing to this day [9][10][11][12].Nevertheless, no reviews have been published on this subject. It should be mentioned that certain methods for the cycloacylation of thioamides by derivatives of unsaturated carboxylic acids were analyzed in reviews on the synthesis of 1,3-thiazines [1] and thiazolidin-4-ones [2, 13], reactions of N-aminoazolinethiones and N-aminoazinethiones [14], thioamides [15][16][17], and carbon suboxide [18]. However, the information on this subject in these publications has not been coordinated and is not exhaustive.New publications on the cycloacylation of thioamides, in which the range of both reagents and substrates has been extended, have appeared recently. Modern physical methods of establishing the structure of the synthesized products were used, and this made it possible to prove their structure unequivocally.For this reason we attempted to fill the gap and to analyze the information concerning the cycloacylation of acyclic and cyclic thioamides by compounds containing an activated multiple bond. This reviews covers papers not examined in [1,2,[13][14][15][16][17][18] and also papers that have appeared more recently.

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“…The application of microwave irradiation in organic synthesis for conducting reactions at highly accelerated rates is an emerging technique 3 . In fact, in recent years, the use of microwave has become popular among synthetic organic chemists both to improve classical organic reactions (shortening reaction times and /or improving yield) as well as to promote new reactions 6 .…”

Section: Introductionmentioning

confidence: 99%

Preparation of heterocyclic compounds by reaction of dimethyl and diethyl acetylene dicarboxylate (DMAD, DEAD) with thiosemicarbazone derivatives

Darehkordi¹,

Saidi²,

Islami³

2007

Arkivoc

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Different thiosemicarbazone derivatives react with dimethyl acetylene dicarboxylate (DMAD) and diethyl acetylene dicarboxylate (DEAD) by three different methods: a) in ethyl acetate solvent at ambient temperature, b) one-pot synthesis under microwave irradiation and solventfree conditions (three-component reaction between thiosemicarbazide, aldehyde/ ketone and DMAD or DEAD), c) a microwave-assisted synthesis under solvent-free conditions, to obtain five-membered S,N-heterocycles thiazolines in good to excellent yields.

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Cycloaddition reactions of polyfluoroalkylthioncarboxylic acid derivatives with dimethyl acetylenedicarboxylate (DMAD)

Cited by 19 publications

References 8 publications

Chemistry of heterocyclic compounds at the Institute of Organic Chemistry, National Academy of Sciences of Ukraine (Review)

Chemistry of heterocyclic compounds at the Institute of Organic Chemistry, National Academy of Sciences of Ukraine (Review)

Cycloacylation of thioamides and their derivatives by compounds containing an activated multiple bond (review)

Preparation of heterocyclic compounds by reaction of dimethyl and diethyl acetylene dicarboxylate (DMAD, DEAD) with thiosemicarbazone derivatives

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