Cycloacylation of N-Phenyl-3-oxobutanethioamide with 3-Aryl-2-propenoyl Chlorides

Britsun, V. N.; Borisevich, A. N.; Samoilenko, L. S.; Lozinskii, M. O.

doi:10.1007/s11178-005-0158-2

Cited by 12 publications

(18 citation statements)

References 6 publications

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“…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. Their derivatives 5 react readily with dienophiles (vinyl ethyl ether) and 1,3-dienes (isoprene and 2,3-dimethyl-1,3-butadiene), being converted into 5H-pyrano[2,3-d]thiazolines 6 and 4-oxo-1-thia-3-azaspiro [4,5] In [25,26] it was established that the thioamides 7 containing an active methylene group react smoothly with acetylenedicarboxylate ester. The reaction is selective with the formation of 2-(R 1 -methylene)-5-ethoxycarbonylmethylene-3-R 2 -1,3-thiazolidin-4-ones 8.…”

Section: Reactions With Acetylenedicarboxylic Estermentioning

confidence: 99%

“…In the opinion of Indian researchers [32], the products from the condensation of 4,5-dihydro-1H-1,2,4-triazole-5-thiones 19 with DMAD in methanol are 5-methoxycarbonyl-2-phenyl-7H-[1,2,4]triazolo[5,1-b]-[1,3]thiazin-7-ones 21, whereas the authors of [33,34] suggest that these compounds have the structure of 7-methoxycarbonyl-3-phenyl[1, 2,4]triazolo [3,4- In [22] it was shown unambiguously by X-ray crystallographic analysis that [1,2,4]triazolo[5,1-b]-[1,3]thiazin-7-ones 21 are produced in this reaction.…”

Section: Reactions With Acetylenedicarboxylic Estermentioning

confidence: 99%

“…The direction of the reaction of thiosemicarbazide 38 with methyl 3-phenylpropiolate also depends on the nature of the solvent -methyl 3-[(4-oxo-6-phenyl-4H-1,3-thiazin-2-yl)hydrazono]-3-phenylpropionate 39 is formed in ethanol and 3-methyl-7-phenyl-5H-[1, 2,4]triazolo [3,4-b][1,3]thiazin-5-one 40 in acetic acid [10] In [42] it was shown that the products from the reaction of 3-R-1,2,4-triazoline-5-thione 42 and 3-trifluoroacetyl(perfluorohexanoyl)thiosemicarbazide 41 with methyl 3-phenylpropiolate in acetic acid (ethanol) are mixtures of two isomeric bicycles - 3]thiazin-7-ones 44, which are obtained with overall yields of 70-80% in a ratio of 10:1. Since the structure of compounds 43 and 44 cannot be identified unambiguously by the data from the IR, 1 H and 13 C NMR, and mass spectra, the structure of the isomers given by the authors [42] is provisional until the results from X-ray diffraction analysis are obtained.…”

Section: Cyclocondensation With Derivatives Of 3-r-propiolic Acidsmentioning

confidence: 99%

“…As a result of their higher reactivity aryl-2-propenoyl chlorides are suitable reagents for the cycloacylation both of dithiocarbamates [49,50,76] and of thioamides with various structures [4,47,48,77]. Unlike acryloyl chloride, 3-aryl-2-propenoyl chlorides do not polymerize when heated and in the presence of bases.…”

Section: Reactions With 3-aryl-2-propenoyl Chloridesmentioning

confidence: 99%

“…However, the amide bond in these compounds is weak, as a result of which they are readily hydrolyzed by water to the corresponding 3-aryl-3-(5-thio-1H-1,2,4-triazol-5-yl)propionic acids 98 [82]. If a compound containing an active methylene group -N-phenyl-3-oxobutanethioamide (99) -is used as substrate, the reaction takes place nonselectively with the formation of three groups of compounds, i.e., thioxopiperidin-2-ones 100, 2,3-dihydro-4H-thiopyran-4-ones 101, and 5,6-dihydro-4H-1,3-thiazin-4-ones 102 [4,83]. The type of heterocycles, their ratio, and the yields depend on the nature of the substituents present in the phenyl ring of the initial 3-aryl-2-propenoyl chlorides.…”

Section: Reactions With 3-aryl-2-propenoyl Chloridesmentioning

confidence: 99%

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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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