Shokol, Т.Т.ShokolШокол, Т.Т.ШоколНесторак, І.І.НесторакВоловенко, Ю.Ю.ВоловенкоХиля, В.В.Хиля2026-04-142026-04-142017-05-25Shokol, Т., Шокол, Т., Несторак, І., Воловенко, Ю., Хиля, В. (2017). SYNTHESIS OF THE NOVEL HETEROCYCLIC SYSTEM 12Н-CHROMENO[3’,2’:3,4]PYRROLO[1,2-a]PYRIMIDIN-12-ONE. Bulletin of the Taras Shevchenko National University of Kyiv. Chemistry(1 (53)), 13–15...https://ir.library.knu.ua/handle/15071834/16008The behavior of 2-pyrimidinylacetonitriles, such as 2-(4,6-dimethyl-2-pyrimidinyl)acetonitrile and 2-(2,6-dimethyl-4-pyrimidinyl)acetonitrile in Houben-Hoesch reaction was investigated. It was found that the result of the reaction depends on the structure of the starting nitrile. The reaction of 2-(4,6-dimethyl-2-pyrimidinyl)acetonitrile and resorcinol or 4-ethylresorcinol in BF3*Et2O with hydrogen chloride, followed by hydrolysis resulted in α-(4,6-dimethyl-2-pyrimidinyl)-2,4-dihydroxyacetophenones, while 2-(2,6-dimethyl-4-pyrimidinyl)acetonitrile in this reaction failed to give α-(2,6-dimethyl-4-pyrimidinyl)-2,4-dihydroxyacetophenone because of the pyrimidine ring-opening. The interaction of α-(4,6-dimethyl-2-pyrimidinyl)-2,4-dihydroxyacetophenones with chloroacetyl chloride in acetonitrile in the presence of pyridine was investigated. α-(4,6-Dimethyl-2-pyrimidinyl)-2,4-dihydroxyacetophenones underwent acylation with chloroacetyl chloride, followed by cyclization to give 2-chloromethyl-7-chloroacetoxy-3-(4,6-dimethyl-2-pyrimidinyl)-4H-4-chromenones, which can undergo subsequent intramolecular cyclization with annelation of pyrrolopyrimidine ring to chromone core. A result of this reaction starting from α-(4,6-dimethyl-2-pyrimidinyl)-2,4-dihydroxyacetophenone is 2,4-dimethyl-12-oxo-12Н-chromeno[3’,2’:3,4]pyrrolo[1,2-a]pyrimidin-9-yl 2-chloroacetate, which is the derivative of the new heterocyclic system 12H-chromeno[3',2':3,4]pyrrolo[1,2-a]pyrimidin-12-one.Досліджено поведінку 2-піримідилацетонітрилів у реакції Губена-Гьоша, встановлено, що результат реакції залежить від будови вихідного нітрилу. Досліджено взаємодію α-(4,6-диметил-2-піримідил)-2,4-дигідроксиацетофенонів з хлорацетилхлоридом. В результаті цієї реакції синтезовано похідну нової гетероциклічної системи 12Н-хромено[3',2':3,4]піроло[1,2-a]піримідин-12-ону.ukacylation2-chloromethyl-3-(46-dimethyl-2-pyrimidinyl)-6-ethyl-7-hydroxy-4H-4-chromenoneintramolecular cyclization2-pyrimidinylacetonitrilesα-pyrimidinyl-24-dihydroxyacetophenones12Н-chromeno[3'2':34]pyrrolo[12-a]pyrimidin-12-one.ацилюваннявнутрішньомолекулярна циклізація7-гідрокси-3-(46-диметил-2-піримідил)-6-етил- 2-хлорометил-4Н-4-хроменон2-піримідилацетонітрилиα-піримідил-24-дигідроксиацетофенони12Н-хромено [3'2':34]піроло[12-a]піримідин-12-он.Стаття