ИССЛЕДОВАНИЕ ВЗАИМОДЕЙСТВИЯ 2-АРИЛ-7,7-ДИМЕТИЛ-5-ОКСО-5,6,7,8-ТЕТРАГИДРОХИНОЛИН-4-КАРБОНОВЫХ КИСЛОТ С БЕНЗОИЛ-И ИЗОНИКОТИНОИЛ-ГИДРАЗИНАМИ Статья посвящена синтезу 5-арил-8,8-диметил-8,9-дигидро-2Н-пиридо[4,3,2-de]циннолин-3(7Н)онов на основе взаимодействия 2-арил-7,7-диметил-5-оксо-5,6,7,8-тетрагидрохинолин-4карбоновых кислот с бензоил-и изоникотиноилгидразинами.Обсуждается схема реакции.

Взаимодействием 2-арил-7,7-диметил-5-оксо-5,6,7,8-тетрагидрохинолин-4-карбоновых кислот с гидроксиламином, N-этил-, фенил-, пентафторфенил-, тозилгидразинами получены замещенные [1,2]оксазино[5,4,3-de]хинолины и пиридо[4,3,2-de]циннолины соответственно. Строение синтезированных соединений подтверждено данными ИК и 1Н ЯМР спектроскопии. Приведены результаты изучения антиоксидантной активности синтезированных соединений в клетках бактерий Escherichia coli BW 25113 на модели окислительного стресса, создаваемого пероксидом водорода. Умеренную антиоксидантную активность проявили 3 соединения из 6, что позволяет в дальнейшем вести поиск веществ, обладающих антиоксидантной активностью среди продуктов реакций замещенных 5,6,7,8-тетрагидрохинолин-4-карбоновых кислот с нуклеофильными агентами.

Substituted [1, 2]oxazino[5,4,3-de]quinolines and pyrido[4,3,2-de]cinnolines were obtained by the reaction of 2-aryl-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydroquinoline-4-carboxylic acids with hydroxylamine and N-ethyl-, phenyl-, pentafluorophenyl-, and tosylhydrazines, respectively. The structures of the synthesized compounds were confirmed using IR and PMR spectroscopy. The antioxidant activity of the synthesized compounds was studied in Escherichia coli BW 25113 cells for an oxidative stress model induced by H2O2. Three of the six compounds exhibited moderate antioxidant activity, which enabled compounds with antioxidant activity to be sought among the reaction products of substituted 5,6,7,8-tetrahydroquinoline-4-carboxylic acids and nucleophilic reagents.

Methyl 7,7-dimethyl-5-oxo-5,6,7,8-tetrahydroquinoline-4-carboxylates were obtained as a result of 3-amino-5,5-dimethylcyclohex-2-enone reaction with the methyl esters of acyl(aroyl)pyruvic acids. The structure of methyl 7,7-dimethyl-5-oxo-2-phenyl-5,6,7,8-tetrahydroquinoline-4-carboxylate was established by X-ray structural analysis.

The reaction of 2-substituted 7,7-dimethyl-5-oxo-5,6,7,8-tetrahydroquinoline-4-carboxylic acids with hydroxylamine results in the formation of 5-substituted 8,8-dimethyl-8,9-dihydro-3 H ,7 H -[1,2]ox-azino[5,4,3- de ]quinolin-3-ones. The structure of the 5-phenyl derivative has been established by X-ray structural analysis. A possible mechanism of the reaction has been proposed on the basis of nonempirical quantum-chemical calculations.

The reaction of 2-substituted 7,7-dimethyl-5-oxo-5,6,7,8-tetrahydroquinoline-4-carboxylic acids with hydrazine was studied. This reaction gave 5-substituted 8,8-dimethyl-3,7,8,9-tetrahydro-2H-pyrido-[4,3,2-de]cinnolin-3-ones in good yields. A possible reaction mechanism was discussed using nonempirical quantum-chemical calculations.

Methods for the synthesis of various heterocyclic compounds based on 3-amino-5,5-dimethylcyclohex-2-enone are discussed.

2-Substituted 7,7-dimethyl-5-oxo-5,6,7,8-tetrahydroquinoline-4-carboxylic acids were synthesized by reaction of acyl- and aroylpyruvic acids with 3-amino-5,5-dimethylcyclohex-2-en-1-one. A plausible mechanism of their formation was proposed on the basis of ab initio quantum-chemical calculations.