Cycloacylation of N-phenyl-N′-R-thioureas with 3-aryl-2-propenoyl chlorides

Britsun, V. N.; Esipenko, A. N.; Lozinskii, M. O.

doi:10.1134/s1070428006110200

Cited by 10 publications

(5 citation statements)

References 9 publications

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“…Treatment with sodium bicarbonate or potassium bicarbonate removed the acid to give 128. 22,78 Boron trifluoride also has been shown to catalyze this type of cyclization. 79…”

Section: Scheme 35mentioning

confidence: 99%

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Chemistry of 1,3-thiazin-4-ones and their derivatives, 1995 - mid-2018

Silverberg¹,

Moyer²

2019

Arkivoc

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This review updates an earlier review published in 1996 by Ryabukhin, Korzhavina, and Suzdalev, which covered the literature through 1994. It deals with the synthesis and reactivity of 1,3-thiazin-4-ones and their derivatives. These include reduced compounds, 2-imino or 2-amino compounds, compounds with fused arenes or heterocycles, bridged compounds, and compounds combining various of these attributes.

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“…Treatment with sodium bicarbonate or potassium bicarbonate removed the acid to give 128. 22,78 Boron trifluoride also has been shown to catalyze this type of cyclization. 79…”

Section: Scheme 35mentioning

confidence: 99%

“…A one-pot reaction was done in which thioureas 132 were reacted with 3-aryl-2-propenoyl chlorides 131 in acetone to give products 133 (Scheme 38). 22 For R = H, the product was the HCl salt of 133. It was presumed that the N-acylation product was formed first, followed by cyclization as in the examples above.…”

Section: Scheme 37mentioning

confidence: 99%

Chemistry of 1,3-thiazin-4-ones and their derivatives, 1995 - mid-2018

Silverberg¹,

Moyer²

2019

Arkivoc

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“…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%

“…The yields of the 1,3-thiazin-4-ones 82 vary between moderate (28%) and quantitative (91%) [49,50]. The cycloacylation of N-R-N'-phenylthioureas 83 by 3-aryl-2-propenoyl chlorides was studied in [77]. A feature of this reaction is the possibility of the formation both of 2,3,5,6-tetrahydro-4H-1,3-thiazin-4-ones and of 1,2,3,5,6-pentahydro-2-thioxo-4H-pyrimidin-4-ones and, in the case of the reaction with unsymmetrical N-phenylurea 83, probably the formation of two 4H-1,3-thiazin-4-ones and two 2-thioxo-4H-pyrimidin-4-ones.…”

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

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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“…Thus, the development of methods for the synthesis of new imidazothiazinotriazines is an urgent task both for the development of organic chemistry methods and for the study of their biological activity. 1,3-Thiazines condensed with heterocycles were prepared by the reactions of azolethiones with propiolic acid derivatives [24][25][26]. In some cases, these reactions gave a mixture of two regioisomers [24] (Scheme 1B).…”

Section: Introductionmentioning

confidence: 99%

Regioselective synthesis of new imidazo[4,5‐e][1,3]thiazino[2,3‐c][1,2,4]triazines via reaction of imidazo[4,5‐e][1,2,4]triazinethiones with ethyl phenylpropiolate

Vinogradov,

Izmest'ev,

Kravchenko

et al. 2023

Journal of Heterocyclic Chem

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A method for the regioselective synthesis of imidazo[4,5‐e][1,3]thiazino[2,3‐c][1,2,4]triazine derivatives has been developed by the reaction of imidazotriazinethiones with ethyl phenylpropiolate upon treatment with potassium carbonate or sodium methoxide in methanol. The synthesis was accomplished by Michael‐type addition of the imidazotriazinethiones to the triple bond of ethyl phenylpropiolate followed by subsequent intramolecular cyclization.

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Cycloacylation of N-phenyl-N′-R-thioureas with 3-aryl-2-propenoyl chlorides

Cited by 10 publications

References 9 publications

Chemistry of 1,3-thiazin-4-ones and their derivatives, 1995 - mid-2018

Chemistry of 1,3-thiazin-4-ones and their derivatives, 1995 - mid-2018

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

Regioselective synthesis of new imidazo[4,5‐e][1,3]thiazino[2,3‐c][1,2,4]triazines via reaction of imidazo[4,5‐e][1,2,4]triazinethiones with ethyl phenylpropiolate

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