Synthesis of N-ethoxycarbonyl-?-aminoketones ?key intermediated for the preparation of nitrogen-containing heterocycles

Sivova, N. V.; Шуталев, А. Д.

doi:10.1007/bf01169693

Cited by 3 publications

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“…Compound 9a was obtained by our convenient modification 30,32,33 of Engberts' method 31 using p-toluenesulfinic…”

Section: Resultsmentioning

confidence: 99%

“…The precipitate was filtered, washed with ice-cold water (4 × 5 mL), then washed thoroughly with petroleum ether to remove chalcone, and dried to give compound 14a (1.285 g, 48%) as a mixture of two conformers in a ratio of 67:33. An analytically pure sample (a 67: 33 A homogeneous solution formed for several minutes, from which solid immediately started to precipitate. After 4 h from the beginning of the reaction, the suspension was cooled to 0 °C.…”

Section: O-ethyl [(2-acetyl-3-oxo-1-phenyl)but-1-yl]thiocarbamate (13)mentioning

confidence: 99%

“…reaction time) and relevant spectroscopic data of the compounds prepared were not provided in the paper. Therefore, it was necessary to develop suitable conditions for formation of thiocarbamates 9a-c.Compound 9a was obtained by our convenient modification 30,32,33 of Engberts' method 31 using p-toluenesulfinic…”

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confidence: 99%

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Thiocarbamate-Based Synthesis of 2,4,5,6-Tetrahydro-3H-1,2,4-Triazepine-3-Thiones

Trafimova¹,

Zimin²,

Шуталев³

2017

Journal of Chemical Research

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A five-step synthesis of 5,7-diaryl-substituted 2,4,5,6-tetrahydro-3H-1,2,4-triazepine-3-thiones starting from ethyl thiocarbamate was developed. The synthesis included a three-component condensation of ethyl thiocarbamate with aromatic aldehydes and p-toluenesulfinic acid to give O-ethyl[(aryl)(tosyl)methyl]thiocarbamates which were transformed into the corresponding O-ethyl (3-phenyl-3-oxopropyl) thiocarbamates by treatment with the sodium enolate of dibenzoylmethane followed by base-promoted retro-Claisen condensation. Reaction of the prepared thiocarbamates with hydrazine and subsequent acid-catalysed cyclisation of the derived 4-[(3-hydrazono-3-phenyl)prop-1-yl]semicarbazides gave the target triazepines.

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“…Compound 9a was obtained by our convenient modification 30,32,33 of Engberts' method 31 using p-toluenesulfinic…”

Section: Resultsmentioning

confidence: 99%

Section: O-ethyl [(2-acetyl-3-oxo-1-phenyl)but-1-yl]thiocarbamate (13)mentioning

confidence: 99%