Synthesis of 2,4-diarylsubstituted 3H-1,5-benzodiazepines by a consecutive three-component reaction of 5-(ethynyl)methylanthranilate with benzoyl chlorides and o-phenylenediamine
K. P. CHEREMNYKH1,2, V. A. SAVELYEV1, A. B. SKOROVA1, E. E. SHULTS1
1Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Novosibirsk, Russia
2Novosibirsk State Pedagogical University, Novosibirsk, Russia
Keywords: 1,5-benzodiazepines, α, β-alkynyl ketones, anthranylic acid, multicomponent reactions
Pages: 724–730
Abstract
The use of the available synthetic platform of 5-ethynyl-N-(acetyl)anthranilic acid in the synthesis of a chemical library of 2,4-diaryl-3H-1,5-benzodiazepines is proposed. The key step of the synthesis included the reaction of in situ generated methyl 2-acetylamino-5-[3-(4-aryl)propiolyl]benzoate with o-phenylenediamine. The selected conditions were used for the synthesis of a chemical library of 3H-1,5-benzodiazepines containing an anthranilic acid methyl ester fragment in the C-2 position. The physicochemical characteristics of intermediately formed α,β-alkynyl ketones are also described.
DOI: 10.15372/CSD2023522
EDN: IDQOGI
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