Synthesis and intramolecular transformations of 8-substituted 11-nitro-2-phenyl-5,6-dihydro-2H-2,6-methanobenzo[g][1,3,5]oxadiazocin-4(3H)-one diastereomers Научная публикация
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Russian Chemical Bulletin
ISSN: 1066-5285 , E-ISSN: 1573-9171 |
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| Вых. Данные | Год: 2016, Том: 65, Номер: 1, Страницы: 215-222 Страниц : 8 DOI: 10.1007/s11172-016-1287-1 | ||
| Ключевые слова | Biginelli reaction; salicylic aldehydes; 11-nitrodihydro-2,6-methanobenzo-[g][1,3,5]oxadiazocin-4(3H)-ones; intramolecular transformations | ||
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Реферат:
The Biginelli reaction between 5-R-salicylic aldehyde (R = H, Me, and Br), alpha-nitroacetophenone, and urea affords 8-R-11-nitro-2-phenyl-5,6-dihydro-2H-2,6-methanobenzo-[g][1,3,5]oxadiazocin-4(3De)-ones as mixtures of two diastereomers. The ratio of diastereomers depends on the catalyst (HCl) concentration in the reaction medium. In DMSO and DMF, the resulting compounds undergo oxadiazocine ring opening with establishment of a three-component equilibrium between 4-(2-hydroxy-5-R-phenyl)-5-nitro-6-phenyl-3,4-dihydropyrimidin-2(1De)-one as the major component and diastereomeric methanobenzoxadiazocines as two minor components. Dilution of these solutions with water favors the oxa-Michael reaction resulting in the reverse transformation of dihydropyrimidinones into the corresponding starting diastereomers.
Библиографическая ссылка:
Sedova V.F.
, Krivopalov V.P.
, Shkurko O.P.
Synthesis and intramolecular transformations of 8-substituted 11-nitro-2-phenyl-5,6-dihydro-2H-2,6-methanobenzo[g][1,3,5]oxadiazocin-4(3H)-one diastereomers
Russian Chemical Bulletin. 2016. V.65. N1. P.215-222. DOI: 10.1007/s11172-016-1287-1 WOS Scopus РИНЦ OpenAlex
Synthesis and intramolecular transformations of 8-substituted 11-nitro-2-phenyl-5,6-dihydro-2H-2,6-methanobenzo[g][1,3,5]oxadiazocin-4(3H)-one diastereomers
Russian Chemical Bulletin. 2016. V.65. N1. P.215-222. DOI: 10.1007/s11172-016-1287-1 WOS Scopus РИНЦ OpenAlex
Оригинальная:
Седова В.Ф.
, Кривопалов В.П.
, Шкурко О.П.
Синтез и внутримолекулярные превращения диастереомеров 8-замещенных 11-нитро-2-фенил-5,6-дигидро-2 н-2,6-метанобензо[ g][1,3,5]оксадиазоцин-4(3 н)-онов
Известия Академии наук. Серия химическая.(RUSS CHEM B+). 2016. №1. С.215-222. РИНЦ
Синтез и внутримолекулярные превращения диастереомеров 8-замещенных 11-нитро-2-фенил-5,6-дигидро-2 н-2,6-метанобензо[ g][1,3,5]оксадиазоцин-4(3 н)-онов
Известия Академии наук. Серия химическая.(RUSS CHEM B+). 2016. №1. С.215-222. РИНЦ
Даты:
| Опубликована в печати: | 1 янв. 2016 г. |
| Опубликована online: | 27 окт. 2016 г. |
Идентификаторы БД:
| Web of science: | WOS:000387229800029 |
| Scopus: | 2-s2.0-84992691654 |
| РИНЦ: | 27584086 |
| OpenAlex: | W2540760291 |