Аннотация:
Heating aldehydes, N,N’-dimethylbarbituric acid and cyclohexane-1,3-diones in water results in fast formation of Knoevenagel–Michael adducts in 82–98% yields. This multicomponent process opens facile, efficient and environmentally benign way to the new functionalized [(2-hydroxy-6-oxocyclohex-1-en-1-yl)(aryl)methyl]pyrimidine-2,4(1H,3H)-diones bearing both barbituric acid and cyclohexane-1,3-dionemoieties separated by arylmethylene spacer, which are promising compounds for biomedical applications including analeptics, anti-AIDS and anticancer remedies.
Образец цитирования:
M. N. Elinson, A. N. Vereshchagin, Yu. E. Anisina, N. A. Leonova, M. P. Egorov, “On water noncatalytic tandem Knoevenagel–Michael reaction of aldehydes, N,N’-dimethylbarbituric acid and cyclohexane-1,3-diones”, Mendeleev Commun., 30:1 (2020), 15–17
Образцы ссылок на эту страницу:
https://www.mathnet.ru/rus/mendc1086
https://www.mathnet.ru/rus/mendc/v30/i1/p15
Эта публикация цитируется в следующих 16 статьяx:
M. N. Elinson, A. N. Vereshchagin, Yu. E. Ryzhkova, K. A. Karpenko, T. M. Iliyasov, V. M. Kalashnikova, M. P. Egorov, “Multicomponent synthesis of new barbituric acid derivatives”, Russ Chem Bull, 73:5 (2024), 1286
Michail N. Elinson, Yuliya E. Ryzhkova, Varvara M. Kalashnikova, Alexander O. Chizhov, Mikhail P. Egorov, “Multicomponent Assembling of Aldehydes, N,N‐Dimethylbarbituric Acid, Malononitrile, and Morpholine Into Unsymmetrical Ionic Scaffold and Its Efficient Cyclization”, Journal of Heterocyclic Chem, 61:11 (2024), 1752
Yuliya E. Ryzhkova, Varvara M. Kalashnikova, Artem N. Fakhrutdinov, Michail N. Elinson, “Green multicomponent approach to novel 5‐[(2H‐Pyran‐3‐yl)(aryl)methyl]‐1,3‐dimethylpyrimidines”, Journal of Heterocyclic Chem, 60:4 (2023), 576
Yuliya E. Ryzhkova, Varvara M. Kalashnikova, Fedor V. Ryzhkov, Michail N. Elinson, “5-(1-(4-Hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)-2-oxo-2-phenylethyl)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione”, Molbank, 2023:2 (2023), M1640
С. Г. Злотин, К. С. Егорова, В. П. Анаников, А. А. Акулов, М. В. Вараксин, О. Н. Чупахин, В. Н. Чарушин, К. П. Брыляков, А. Д. Аверин, И. П. Белецкая, Е. Л. Доленговский, Ю. Г. Будникова, О. Г. Синяшин, З. Н. Гафуров, А. О. Кантюков, Д. Г. Яхваров, А. В. Аксенов, М. Н. Элинсон, В. Г. Ненайденко, А. М. Чибиряев, Н. С. Нестеров, Е. А. Козлова, О. Н. Мартьянов, И. А. Балова, В. Н. Сорокоумов, Д. А. Гук, Е. К. Белоглазкина, Д. А. Леменовский, И. Ю. Чукичева, Л. Л. Фролова, Е. С. Изместьев, И. А. Дворникова, А. В. Попов, А. В. Кучин, Д. М. Борисова, А. А. Калинина, А. М. Музафаров, И. В. Кучуров, А. Л. Максимов, А. В. Золотухина, “Парадигма зеленой химии в современном органическом синтезе”, Усп. хим., 92:12 (2023), RCR5104 ; S. G. Zlotin, K. S. Egorova, V. P. Ananikov, A. A. Akulov, M. V. Varaksin, O. N. Chupakhin, V. N. Charushin, K. P. Bryliakov, A. D. Averin, I. P. Beletskaya, E. L. Dolengovski, Yu. H. Budnikova, O. G. Sinyashin, Z. N. Gafurov, A. O. Kantyukov, D. G. Yakhvarov, A. V. Aksenov, M. N. Elinson, V. G. Nenajdenko, A. M. Chibiryaev, N. S. Nesterov, E. A. Kozlova, O. N. Mart'yanov, I. A. Balova, V. N. Sorokoumov, D. A. Guk, E. K. Beloglazkina, D. A. Lemenovskii, I. Yu. Chukicheva, L. L. Frolova, E. S. Izmest'ev, I. A. Dvornikova, A. V. Popov, A. V. Kutchin, D. M. Borisova, A. A. Kalinina, A. M. Muzafarov, I. V. Kuchurov, A. L. Maksimov, A. V. Zolotukhina, “The green chemistry paradigm in modern organic synthesis”, Russian Chem. Reviews, 92:12 (2023), RCR5104
Madhvi, Divya Utreja, Shivali Sharma, “Barbiturates: A Review of Synthesis and Antimicrobial Research Progress”, COS, 19:1 (2022), 31
Madhvi, D. Utreja, A. Kalia, “Efficient p-Toluenesulfonic Acid-Catalyzed Synthesis of 5-Aryl-5,10-dihydropyrimido[4,5-b]quinoline-2,4(1H,3H)-diones and Their Antimicrobial Activity”, Russ J Org Chem, 58:9 (2022), 1327
M. N. Elinson, A. N. Vereshchagin, Y. E. Ryzhkova, K. A. Karpenko, I. E. Ushakov, O. I. Maslov, M. P. Egorov, “Four-component transformation of benzaldehydes, dimethylbarbituric acid, 4-hydroxy-6-methyl-2H-pyran-2-one, and morpholine into the unsymmetrical ionic scaffold with three different heterocyclic rings”, Russ Chem Bull, 71:3 (2022), 464
M. N. Elinson, Yu. E. Ryzhkova, V. M. Kalashnikova, M. P. Egorov, “Noncatalytic on water aldol reaction of isatins with cyclic 1,3-diketones at room temperature without the need for subsequent chromatography”, Mendeleev Commun., 32:4 (2022), 543–545
K. P. Trainov, R. F. Salikov, A. Yu. Belyy, A. N. Kuznetsova, M. D. Khitrov, M. K. Ilyushchenko, A. D. Sokolova, D. N. Platonov, Yu. V. Tomilov, “Generation and cascade reactions of N-[1,2-bis(methoxycarbonyl)vinyl]pyridinium species”, Mendeleev Commun., 32:2 (2022), 262–264
Michail N. Elinson, Anatoly N. Vereshchagin, Yuliya E. Ryzhkova, Mikhail P. Egorov, “Selective and efficient electrocatalytic way to spirobarbituric dihydrofurans”, Mendeleev Communications, 31:3 (2021), 347
Fedor V. Ryzhkov, Michail N. Elinson, Yuliya E. Ryzhkova, Anatoly N. Vereshchagin, Artem N. Fakhrutdinov, Mikhail P. Egorov, “Electrocatalytic cascade approach to the synthesis of dihydro-2'H,3H-spiro[1-benzofuran-2,5'-pyrimidines]”, Chem Heterocycl Comp, 57:6 (2021), 672
Yuliya E. Ryzhkova, Artem N. Fakhrutdinov, Michail N. Elinson, “Green on-water multicomponent approach for the synthesis of pyrrolo[2,3-d]pyrimidines”, Tetrahedron Letters, 81 (2021), 153336
Fedor V. Ryzhkov, Michail N. Elinson, Yuliya E. Ryzhkova, Anatoly N. Vereshchagin, Victor A. Korolev, Mikhail P. Egorov, “Pseudo‐four‐component synthesis and in silico studies of 5‐(5‐hydroxy‐3‐methyl‐1H‐pyrazol‐4‐yl)‐substituted 5H‐chromeno[2,3‐b]pyridines”, Journal of Heterocyclic Chem, 58:3 (2021), 793
M. N. Elinson, A. N. Vereshchagin, Yu. E. Ryzhkova, K. A. Karpenko, I. E. Ushakov, “Four component tandem Knoevenagel–Michael strategy for the assembly of arylaldehydes, N,N'-dimethylbarbituric acid, 4-hydroxy-6-methyl-2H-pyran-2-one and morpholine into unsymmetrical scaffold with three different heterocyclic rings”, Mendeleev Commun., 31:5 (2021), 698–700
V. A. Osyanin, I. A. Semenova, A. G. Groshev, D. V. Osipov, Yu. N. Klimochkin, “A cascade formation of N-pyridylacrylamides from pyrido[1,2-a]pyrimidine diones and chromene aldehydes”, Mendeleev Commun., 31:6 (2021), 859–861
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