7 results on '"cyclic condensation"'
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2. The synthesis of polisubstituted thienylpyrroles and the study of their activity as plant growth stimulators
- Author
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O. I. Mikhedkina, O. S. Pelipets, I. V. Peretiatko, D. T. Kozhich, I. I. Melnik, O. V. Tsygankov, I. I. Klimenko, and M. V. Vasyleiko
- Subjects
4-(5-carboxythiophen-2-yl)-pyrol-2(3)-carboxylic acids ,ethyl 4(5)-acetylpyrrol-2(3)-carboxylates ,plant growth regulators ,cyclic condensation ,Chemistry ,QD1-999 - Abstract
Aim. To develop the optimal method for the synthesis of new polysubstituted thienylpyrroles and study them as cereal growth stimulants. Results and discussion. Preparative methods for the synthesis of 4-(5-carboxythiophen-2-yl)-3,5-dimethyl-1H-pyrrole-2-carboxylic acid, 5-(5-carboxythiophen-2-yl)-2,4-dimethyl-1H-pyrrol-3-carboxylic acid and ethyl 4-(4-amino-5)-thoxycarbonyl (thiophen-2-yl)-3,5-dimethyl-1H-pyrrole-2-carboxylate have been developed by step reactions. 4-(5-Carboxythiophen-2-yl)-3,5-dimethyl-1H-pyrrole-2-carboxylic acid is the most promising for the study of the growth-stimulating activity on grain seeds. Experimental part. Using ethyl 4-acyl-3,5-dimethyl-1H-pyrrole-2-carboxylate and ethyl 5-acetyl-2,4-dimethyl- 1H-pyrrole-3-carboxylate as starting compounds 4-(5-carboxythiophen-2-yl)-3,5-dimethyl-1H-pyrrole-2-carboxylic and 5-(5-carboxythiophen-2-yl) 2,4-dimethyl-1H-pyrrol-3-carboxylic acid were obtained. By the action of the Wilsmeier-Haack reagent on the latter the corresponding pyrroles with the chlorvinylcarbaldehyde fragment were isolated; their post-cyclization with ethyl ester of thioglycolic acid and the subsequent hydrolysis leads to the formation of thienylpyroldicarboxylic acids. The study of the physiological activity of the compounds synthesized was performed on seeds of different varieties of wheat and barley. Conclusions. By means of sequential reactions the polysubstituted thienylpyrrolcarboxylic acids previously unknown and their esters have been synthesized. The features of the study of these compounds as plant growth stimulants have been revealed.
- Published
- 2019
- Full Text
- View/download PDF
3. Simple Synthesis of Multi-Halogen Pyrazino[1,2- a]indole-1,8(2 H,5 aH)-diones.
- Author
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Yang, Rui-Xia, Zhao, Yu-Cheng, Kong, Ling-Bin, Yan, Sheng-Jiao, and Lin, Jun
- Subjects
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ESTERS , *CHEMICAL synthesis , *INDOLE compounds , *BENZOQUINONES , *CATALYSTS , *HALOGEN compounds - Abstract
A concise and efficient one-pot synthesis of multi-halogen pyrazino[1,2- a]indole-1,8(2 H,5 aH)-dione ( MHPID) derivatives by the reaction of an enamino ester with multi-halogen benzoquinone derivatives is described. MHPIDs 3a-3d were obtained with good yields (78-83%) by refluxing enamino esters 1a and 1b and tetrahalogen-1,4-benzoquinones 2a and 2b for 24 h without the use of catalysts. Compounds 3e-3p were also obtained with excellent yields (69-92%) via the reaction of the phenyl-substituted enamino esters 1c-1h with tetrahalogen-1,4-benzoquinones 2a and 2b in CH3CN catalyzed by Cs2CO3. These two protocols are efficient and effective for the synthesis of MHPIDs. [ABSTRACT FROM AUTHOR]
- Published
- 2016
- Full Text
- View/download PDF
4. Synthesis of new quinolinones from 3-nitropyranoquinolinones.
- Author
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Morsy, Jehan M., Hassanin, Hany M., Ismail, Mostafa M., Marwa, M.A., and Abd-Alrazk
- Subjects
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QUINOLONE antibacterial agents , *ANTIBACTERIAL agents , *QUINOLINE , *SYNTHETIC drugs , *CINOXACIN - Abstract
Alkaline hydrolysis of 3-nitropyranoquinolinones (6-alkyl-4-hydroxy-3-nitro-2H-pyrano[3,2-c]quinoline-2,5(6H)-diones) for different reaction times gave five products which were formed by the progressive degradation of the nitropyrano ring. Varying amounts of 3-nitroacetylquinolinones, quinolinones with side-chains of β- and α -ketoacids, quinolinone-3-carboxylic acids and 4-hydroxyquinolinones were isolated. With the aim of preparing new biologically active quinolone derivatives, the products of reaction of the 3-nitropyranoquinolinones with side-chains of β- and α-ketoacids with some nitrogen and carbon nucleophiles were also studied, some giving rise to annulated products. [ABSTRACT FROM AUTHOR]
- Published
- 2016
- Full Text
- View/download PDF
5. The synthesis of polisubstituted thienylpyrroles and the study of their activity as plant growth stimulators
- Author
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Mikhedkina, O. I., Pelipets, O. S., Peretiatko, I. V., Kozhich, D. T., Melnik, I. I., Tsygankov, O. V., Klimenko, I. I., Vasyleiko, M. V., Mikhedkina, O. I., Pelipets, O. S., Peretiatko, I. V., Kozhich, D. T., Melnik, I. I., Tsygankov, O. V., Klimenko, I. I., and Vasyleiko, M. V.
- Abstract
Aim. To develop the optimal method for the synthesis of new polysubstituted thienylpyrroles and study them as cereal growth stimulants.Results and discussion. Preparative methods for the synthesis of 4-(5-carboxythiophen-2-yl)-3,5-dimethyl-1H-pyrrole-2-carboxylic acid, 5-(5-carboxythiophen-2-yl)-2,4-dimethyl-1H-pyrrol-3-carboxylic acid and ethyl 4-(4-amino-5)-thoxycarbonyl (thiophen-2-yl)-3,5-dimethyl-1H-pyrrole-2-carboxylate have been developed by step reactions. 4-(5-Carboxythiophen-2-yl)-3,5-dimethyl-1H-pyrrole-2-carboxylic acid is the most promising for the study of the growth-stimulating activity on grain seeds.Experimental part. Using ethyl 4-acyl-3,5-dimethyl-1H-pyrrole-2-carboxylate and ethyl 5-acetyl-2,4-dimethyl-1H-pyrrole-3-carboxylate as starting compounds 4-(5-carboxythiophen-2-yl)-3,5-dimethyl-1H-pyrrole-2-carboxylic and 5-(5-carboxythiophen-2-yl) 2,4-dimethyl-1H-pyrrol-3-carboxylic acid were obtained. By the action of the Wilsmeier-Haack reagent on the latter the corresponding pyrroles with the chlorvinylcarbaldehyde fragment were isolated; their post-cyclization with ethyl ester of thioglycolic acid and the subsequent hydrolysis leads to the formation of thienylpyroldicarboxylic acids. The study of the physiological activity of the compounds synthesized was performed on seeds of different varieties of wheat and barley.Conclusions. By means of sequential reactions the polysubstituted thienylpyrrolcarboxylic acids previously unknown and their esters have been synthesized. The features of the study of these compounds as plant growthstimulants have been revealed., Цель работы – разработка оптимального метода синтеза новых полизамещенных тиенилпирролов и их исследование в качестве стимуляторов роста зерновых культур.Результаты и их обсуждение. Путем ступенчатых реакций были разработаны препаративные методики синтеза 4-(5-карбокситиофен-2-ил)-3,5-диметил-1H-пиррол-2-карбоновой кислоты, 5-(5-карбокситиофен-2-ил)-2,4-диметил-1Н-пиррол-3-карбоновой кислоты и этил4-(4-амино-5)-этоксикарбонил(тиофен-2-ил)-3,5-диметил-1H-пиррол-2-карбоксилата. Наиболее перспективной для исследования ростстимулирующей активности на семенах зерновых стала 4-(5-карбокситиофен-2-ил)-3,5-диметил-1H-пиррол-2-карбоновая кислота.Экспериментальная часть. Были получены 4-(5-карбокситиофен-2-ил)-3,5-диметил-1H-пиррол-2-карбоновая и 5-(5-карбокситиофен-2-ил)-2,4-диметил-1H-пирол-3-карбоновая кислоты с использованием в качестве исходных соединений этил 4-ацетил-3,5 диметил-1H-пиррол-2-карбоксилат и этил 5-ацетил-2,4-диметил-1Н-пиррол-3-карбоксилат. Действием реагента Вильсмайера-Хаака на последние выделены соответствующие пирролы с хлорвинилкарбальдегидным фрагментом, пост-циклизация которых с этиловым эфиром тиогликолевой кислоты и последующим гидролизом приводит к образованию тиенилпирролдикарбоновых кислот. Исследование физиологической активности синтезированных соединений проводили на семенах различных сортов пшеницы и ячменя.Выводы. Путем последовательных реакций синтезировали неизвестные ранее полизамещенные тиенилпирролкарбоновые кислоты и их эфиры. Выявлены особенности исследования этих соединений в качестве стимуляторов роста растений., Мета роботи – розробка оптимального методу синтезу нових полізаміщених тієнілпіролів і їх дослідження в якості стимуляторів росту зернових культур.Результати та їх обговорення. Шляхом ступінчастих реакцій були розроблені препаративні методики синтезу 4-(5-карбокситіофен-2-іл)-3,5-диметил-1Н-пірол-2-карбонової кислоти, 5-(5-карбокситіофен-2-іл)-2,4-диметил-1Н-пірол-3-карбонової кислоти та етил-4-(4-аміно-5)-етоксикарбоніл(тіофен-2-іл)-3,5-диметил-1Н-пірол-2-карбоксилату. Найбільш перспективною для дослідження рістстимулюючої активності на насінні зернових стала 4-(5-карбокситіофен-2-іл)-3,5-диметил-1Н-пірол-2-карбонова кислота.Експериментальна частина. Були одержані 4-(5-карбокситіофен-2-іл)-3,5-диметил-1Н-пірол-2-карбонова та 5-(5-карбокситіофен-2-іл)-2,4-диметил-1Н-пірол-3-карбонова кислоти, в яких в якості вихідних сполук використовували етил 4-ацетил-3,5-диметил-1Н-пірол-2-карбоксилат та етил 5-ацетил-2,4-диметил-1Н-пірол-3-карбоксилат. Дією реагенту Вільсмайєра-Хаака на останні виділені відповідні піроли з хлоровініл-карбальдегідним фрагментом, пост-циклізація яких з етиловим естером тіогліколевої кислоти та наступнимгідролізом приводить до утворення тієнілпіролдикарбонових кислот. Дослідження фізіологічної активності синтезованих сполук проводили на насінні різних сортів пшениці та ячменю.Висновки. Шляхом послідовних реакцій синтезували невідомі раніше тієнілпіролкарбонов
- Published
- 2019
6. Phosphomolybdic Acid Catalyzed Synthesis of 1,2,4,5-Tetraoxanes.
- Author
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Xing Yan, Jinglei Chen, Yun-Ting Zhu, and Chunhua Qiao
- Subjects
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PHOTOCATALYSIS , *KETONES , *HYDROGEN bromide , *CHEMICAL reactions , *ORGANIC compounds , *CATALYSTS - Abstract
1,1-Dihydroperoxides were converted into 1,2,4,5-tetraoxanes through condensation with the corresponding ketones in 36-91% yields using phosphomolybdic acid as the catalyst and anhydrous MgSO4 as the water scavenger. [ABSTRACT FROM AUTHOR]
- Published
- 2011
- Full Text
- View/download PDF
7. Synthesis of glycoluril catalyzed by potassium hydroxide under ultrasound irradiation
- Author
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Li, Ji-Tai, Liu, Xiao-Ru, and Sun, Ming-Xuan
- Subjects
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ORGANIC synthesis , *CATALYSIS , *ALKYNES , *POTASSIUM hydroxide , *ULTRASONICS , *IRRADIATION , *TEMPERATURE effect - Abstract
Abstract: Synthesis of the glycolurils catalyzed by potassium hydroxide was carried out in 17–75% yield at 40°C in EtOH under ultrasound irradiation. Compared to the method using stirring, the main advantage of the present procedure is milder conditions and shorter reaction time. [Copyright &y& Elsevier]
- Published
- 2010
- Full Text
- View/download PDF
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