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

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

Журнал

Russian Chemical Bulletin
ISSN: 1066-5285 , E-ISSN: 1573-9171

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

Авторы

Sedova V.F. ¹ , Krivopalov V.P. ¹ , Shkurko O.P. ¹

Организации

1	(Данные Web of science) Siberian Branch Russian Acad Sci, NN Vorozhtsov Novosibirsk Inst Organ Chem, 9 Prosp Akad Lavrenteva, Novosibirsk 630090, Russia

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.

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

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

Опубликована в печати:	1 янв. 2016 г.
Опубликована online:	27 окт. 2016 г.

Web of science	WOS:000387229800029
Scopus	2-s2.0-84992691654
РИНЦ	27584086
OpenAlex	W2540760291