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 Full article
| Journal |
Russian Chemical Bulletin
ISSN: 1066-5285 , E-ISSN: 1573-9171 |
||
|---|---|---|---|
| Output data | Year: 2016, Volume: 65, Number: 1, Pages: 215-222 Pages count : 8 DOI: 10.1007/s11172-016-1287-1 | ||
| Tags | Biginelli reaction; salicylic aldehydes; 11-nitrodihydro-2,6-methanobenzo-[g][1,3,5]oxadiazocin-4(3H)-ones; intramolecular transformations | ||
| Authors |
|
||
| Affiliations |
|
Abstract:
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.
Cite:
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
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
ArticleLinkType.TRANSLATED_TO_ORIGINAL:
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
Dates:
| Published print: | Jan 1, 2016 |
| Published online: | Oct 27, 2016 |
Identifiers:
| Web of science | WOS:000387229800029 |
| Scopus | 2-s2.0-84992691654 |
| Elibrary | 27584086 |
| OpenAlex | W2540760291 |