über die Umsetzung von Thioamiden mit Diphenylcyclopropenon

Walter, Wolfgang; Krohn, Jürgen

doi:10.1002/jlac.19717520116

Cited by 13 publications

(4 citation statements)

References 3 publications

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“…The analytical data are provided as follows. Compounds 3a , 3b , 3d , 3h , 3j , 3l , 3m , 3n , 3y , 4a , 4b , 4c , 4e , 4f , 4m , 4n , 4o , 4u , 4v , 6 , 8c , and 9c are known compounds, and their analytical data are consistent with those reported.…”

Section: Methodssupporting

confidence: 87%

Phosphine-Catalyzed Stereoselective Ring-Opening Addition of Cyclopropenones with Nucleophiles

Jiao

Tang

et al. 2023

J. Org. Chem.

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A phosphine-catalyzed ring-opening addition reaction of cyclopropenones with a variety of nucleophiles (NuH), including oxygen-, nitrogen-, sulfur-, and carbon-based ones, has been investigated, which produces potentially useful α,βunsaturated carbonyl derivatives in high yields (up to 99%), high regioselectivity, and exclusive E-selectivity. The reaction proceeds in high efficiency under very mild conditions using only 1 mol % PPh 3 as the catalyst at room temperature. The method is also amenable for the synthesis of deuterated alkenes when deuterated nucleophiles (NuD) are employed. The mechanism is investigated by experiments and DFT calculations, which suggests an α-ketenyl phosphorus ylide as a key intermediate in the catalytic cycle that captures the nucleophiles in a stereoselective manner.

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Section: Methodssupporting

confidence: 87%

Phosphine-Catalyzed Stereoselective Ring-Opening Addition of Cyclopropenones with Nucleophiles

Jiao

Tang

et al. 2023

J. Org. Chem.

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“…Depending on the structure of the cycloacylating agent, the first stage can be both addition of its activated double bond at the thioxo group of the substrate [44,45] and N-acylation of the substrate [46][47][48]. The products from S-acylation of compounds containing a thioamide group are formed much more rarely, and they are less stable than the N-acylation products.…”

Section: Cycloacylation Of Thioamides and Their Derivatives By Compoumentioning

confidence: 96%

“…-diphenyluracil (139) and 4H-[1,3]thiazino[3,2-a]indol-4-one 140.With 2,3-diphenylcyclopropenone 142 the thioamides 141 form N-(2,3-diphenylpropenoyl)thioamides 143, which undergo cyclization to 1,3-thiazin-4-ones 144 when heated[46]:…”

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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“…By acylation of thioimidates the new thioimidates (287; equation 153) were obtained, which are in equilibrium with ketene S,N-acetals 597. …”

mentioning

confidence: 99%

Synthesis of Iminium Salts, Orthoesters and Related Compounds

Kantlehner

1991

Comprehensive Organic Synthesis

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über die Umsetzung von Thioamiden mit Diphenylcyclopropenon

Abstract: Thioamide reagieren mit Diphenylcyclopropenon zu N-(E)-[2-Phenyl-cinnamoyl]-thioamiden 2 (Tab. l), aus denen durch Cyclisierung 1.3-Thiazin-4-one 3 (Tab. 2) bzw. 4 (Tab. 3) hervorgehen.

Cited by 13 publications

References 3 publications

Phosphine-Catalyzed Stereoselective Ring-Opening Addition of Cyclopropenones with Nucleophiles

Phosphine-Catalyzed Stereoselective Ring-Opening Addition of Cyclopropenones with Nucleophiles

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

Synthesis of Iminium Salts, Orthoesters and Related Compounds

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