Synthesis and intramolecular conversion of substituted 2-methyl-11-nitro-5,6-dihydro-2H-2,6-methanobenzo[g] [1,3,5] oxadiazocin-4(3H)-ones in different solvents Full article
| Journal |
Russian Chemical Bulletin
ISSN: 1066-5285 , E-ISSN: 1573-9171 |
||
|---|---|---|---|
| Output data | Year: 2014, Volume: 63, Number: 6, Pages: 1378-1385 Pages count : DOI: 10.1007/s11172-014-0606-7 | ||
| Tags | salicylic aldehydes; Biginelli reaction; nitrodihydro-2,6-methanobenzo[1,3,5]oxadiazocin-4(311)-ones; intramolecular transformations | ||
| Authors |
|
||
| Affiliations |
|
Abstract:
A Biginelli reaction of 5-R-salicylic aldehydes (R = H, Me, Br) with nitroacetone and urea in each case leads to a predominant formation of 2R*,6S*,11S* diastereomers of 8-R-2-methy1-11 -nitro-5,6-dihydro-2H-2,6-methanobenzo [g][1, 3, 5] oxadiazoc in-4(311)-one. In solutions in DMF and DMSO, these diastereomers undergo the oxadiazocine ring opening with setting a three-component equilibrium between predominant 4-(2-hydroxy-5-R-pheny1)-6-methy15-nitro-3,4-dihydropyrimidin-2(11/)-ones and 2R*,6S*,11S* and 2R*,6S*,11R* diastereomers of methanobenzoxadiazocine as two minor components.
Cite:
Sedova V.F.
, Krivopalov V.P.
, Gatilov Y.V.
, Shkurko O.P.
Synthesis and intramolecular conversion of substituted 2-methyl-11-nitro-5,6-dihydro-2H-2,6-methanobenzo[g] [1,3,5] oxadiazocin-4(3H)-ones in different solvents
Russian Chemical Bulletin. 2014. V.63. N6. P.1378-1385. DOI: 10.1007/s11172-014-0606-7 WOS Scopus РИНЦ
Synthesis and intramolecular conversion of substituted 2-methyl-11-nitro-5,6-dihydro-2H-2,6-methanobenzo[g] [1,3,5] oxadiazocin-4(3H)-ones in different solvents
Russian Chemical Bulletin. 2014. V.63. N6. P.1378-1385. DOI: 10.1007/s11172-014-0606-7 WOS Scopus РИНЦ
ArticleLinkType.TRANSLATED_TO_ORIGINAL:
Седова В.Ф.
, Кривопалов В.П.
, Гатилов Ю.В.
, Шкурко О.П.
Синтез и внутримолекулярные превращения замещенных 2-метил-11-нитро-5,6-дигидро-2 н-2,6-метанобензо[ g][1,3,5]оксадиазоцин-4(3 н)-онов в зависимости от среды
Известия Академии наук. Серия химическая.(RUSS CHEM B+). 2014. №6. С.1378. РИНЦ
Синтез и внутримолекулярные превращения замещенных 2-метил-11-нитро-5,6-дигидро-2 н-2,6-метанобензо[ g][1,3,5]оксадиазоцин-4(3 н)-онов в зависимости от среды
Известия Академии наук. Серия химическая.(RUSS CHEM B+). 2014. №6. С.1378. РИНЦ
Dates:
| Published print: | Jun 1, 2014 |
| Published online: | Mar 7, 2015 |
Identifiers:
| Web of science | WOS:000350877500018 |
| Scopus | 2-s2.0-84924229120 |
| Elibrary | 24039682 |
| OpenAlex | W2460512259 |