Methyl 3-aroyl-4-oxo-1,4-dihydroquinoline-2-carboxylates: synthesis and molecular and crystal structures

Boteva, A. A.; Красных, О. П.; Fefilova, I. V.; Бабушкина, Е. Б.; Слепухин, П. А.

doi:10.1007/s11172-014-0499-5

Cited by 2 publications

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“…At thermolysis of 4-acyl-1-aryl-1H-pyrrole-2,3-diones 1.1, N-aryl substituted acyl (imidoyl)ketenes A1 are generated, which undergo intramolecular cyclization through acylation of the ortho CH group of the benzene ring at nitrogen atom by the ketene moiety to result in quinoline-4(1H)-ones 5 (Scheme 3) [36][37][38]40,[46][47][48][49][50][51]. The presence of one substituent in the ortho position of the benzene ring at nitrogen atom in 4-acyl-1-aryl-1Hpyrrole-2,3-diones 1.1 and, further, in ketenes A1, does not influence the reaction mode, and does not reduce the yields of compounds 5, which reflects the ease of the intramolecular acylation process [47].…”

Section: Immediate Transformations Of Acyl(imidoyl)ketenes Via Intram...mentioning

confidence: 99%

Acyl(imidoyl)ketenes: Reactive Bidentate Oxa/Aza-Dienes for Organic Synthesis

2021

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Polyfunctional building blocks are essential for the implementation of diversity-oriented synthetic strategies, highly demanded in small molecule libraries’ design for modern drug discovery. Acyl(imidoyl)ketenes are highly reactive organic compounds, bearing both oxa- and aza-diene moieties, conjugated symmetrically to the ketene fragment, enabling synthesis of various skeletally diverse heterocycles on their basis. The highlights of reactions utilizing acyl(imidoyl)ketenes are high yields, short reaction time (about several minutes), high selectivity, atom economy, and simple purification procedures, which benefits the drug discovery. The present review focuses on the approaches to thermal generation of acyl(imidoyl)ketenes, patterns of their immediate transformations via intra- and intermolecular reactions, including the reactions of cyclodimerization, in which either symmetric or dissymmetric heterocycles can be formed. Recent advances in investigations on mechanisms, identifications of intermediates, and chemo- and regioselectivity of reactions with participation of acyl(imidoyl)ketenes are also covered.

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