Condensations of thioamides with acetylenecarboxylic acid derivatives

Danilkina, Natalia A.; Mikhailov, L. E.; Ivin, B. A.

doi:10.1134/s1070428006060017

Cited by 40 publications

(53 citation statements)

References 54 publications

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“…Reactions of this group were analyzed quite comprehensively in the recently published review [17]. We nevertheless consider it necessary to present the following information.…”

Section: Cycloacylation Of Thioamides and Their Derivatives By Compoumentioning

confidence: 99%

“…This reviews covers papers not examined in [1,2,[13][14][15][16][17][18] and also papers that have appeared more recently.…”

mentioning

confidence: 98%

“…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.…”

mentioning

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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“…Reactions of this group were analyzed quite comprehensively in the recently published review [17]. We nevertheless consider it necessary to present the following information.…”

Section: Cycloacylation Of Thioamides and Their Derivatives By Compoumentioning

confidence: 99%

“…This reviews covers papers not examined in [1,2,[13][14][15][16][17][18] and also papers that have appeared more recently.…”

mentioning

confidence: 98%

mentioning

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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“…Известно, что тиоацетомиды яв-ляются удобными синтетическими блоками для получения различных гетероциклов, в том числе и тиазо-лов, содержащие двойные экзоци-клические связи [12,13]. Несмотря на это, реакция между хлоруксусным эфиром и дитиомалонамидами из-учена недостаточно [14].…”

Section: Introductionunclassified

Synthesis of 2-(5-arylidene-4-oxo-3-arylthiazolydine-2)-N-phenylethanthiamides derivatives from malondithioamides

Обыденнов¹,

Golovko²,

Morzherin³

2014

Chim.Tech.Acta

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It is shown that thioacetamide are comfortable synthetic blocks for various heterocycles, including thiazole containing a double exocyclic bonds. This work describes the synthesis of (Z)-2-((Z)-5-arylidene-4-oxo-3-arylthiazolidin-2-ylidene)-N-arylethanethioamide 4 obtained from the Knoevenagel condensation of (Z)-2-(4-oxo-3-arylthiazolidin-2-ylidene)-N-arylylethanethioamide 2. The starting material 2 was synthesized by a Hantzsch reaction of N,N`-diarylmalondithioamides 1 and ethyl 2-chloroacetate. The structures of the obtained products were established by NMR and the structural features are discussed. Several 4-oxothiazolidin-2-ylidenes were studied by UV-visible spectroscopy technique

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“…Thioamides are not only serve as versatile synthetic intermediates for the construction of pharmacologically important molecules containing nitrogen and sulfur heterocycles [1][2][3][4][5][6][7] but are also used as antitumor agents and enzyme inhibitors [8][9][10]. Thioamide based drugs such as ethionamide (ETH) and prothionamide (PTH) have been widely used for many years in the treatment of mycobacterial infections caused by Mycobacterium tuberculosis, M. leprae and M. avium complex infections [11,12].…”

Section: Introductionmentioning

confidence: 99%

L-Proline: An Efficient and Selective Catalyst for Transamidation of Thioamides with Amines

Adimurthy¹

2016

J Biomol Res Ther

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Condensations of thioamides with acetylenecarboxylic acid derivatives

Cited by 40 publications

References 54 publications

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

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

Synthesis of 2-(5-arylidene-4-oxo-3-arylthiazolydine-2)-N-phenylethanthiamides derivatives from malondithioamides

L-Proline: An Efficient and Selective Catalyst for Transamidation of Thioamides with Amines

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