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Synthesis of new stereoisomeric nitrate esters derived from isosorbide-mononitrate II: Bicyclic delta-lactams and tetrahydrofuran derivatives
dc.creator | Tokić-Vujošević, Zorana | |
dc.creator | Ceković, Z | |
dc.date.accessioned | 2019-09-02T10:53:40Z | |
dc.date.available | 2019-09-02T10:53:40Z | |
dc.date.issued | 2001 | |
dc.identifier.issn | 0039-7881 | |
dc.identifier.uri | https://farfar.pharmacy.bg.ac.rs/handle/123456789/303 | |
dc.description.abstract | The synthesis of the diastereomeric nitrate esters (3R,4R)-(2-hydroxy-4-nitrooxytetrahydrofuran-3-yloxy)acetonitrile (5b) and (3R,4S)-(2-hydroxy-4-nitrooxytetrahydrofuran-3-yloxy)acetonitrile (9) was achieved by the Beckmann fragmentation of 1,4:3,6-dianhydro-D-glucitol-5-(or -2-)nitrate-2-(or -5-)ketoximes (4b and 8), respectively. The bicyclic delta -lactams, (1R,6R,7R)-N-methyl-7-endo-nitrooxy-3-oxo-5,9-dioxa-2-azabicy-clo[4.3.0]nonane (15b) and the stereoisomer (1R,6R,7S)-7-exo-nitrooxy-3-oxo-5,9-dioxa-2-azabicyclo[4.3.0]nonane (18b) were prepared by the Beckmann rearrangement of nitrones 14b and 17b, respectively. The stereoisomeric delta -lactams, N-methyl-7-endo-benzoyloxy- (15a) and N-methyl-7-exo-benzoyloxy-3-oxo-5,9-dioxa-2-azabicyclo[4.3.0]nonane (18a) were prepared from the corresponding nitrones 14a and 17a, respectively. | en |
dc.publisher | Georg Thieme Verlag | |
dc.rights | restrictedAccess | |
dc.source | Synthesis | |
dc.subject | Beckmann rearrangement | en |
dc.subject | Heterocycles | en |
dc.subject | Isosorbide ketonitrates | en |
dc.subject | Nitrones | en |
dc.subject | δ-lactams | en |
dc.title | Synthesis of new stereoisomeric nitrate esters derived from isosorbide-mononitrate II: Bicyclic delta-lactams and tetrahydrofuran derivatives | en |
dc.type | article | |
dc.rights.license | ARR | |
dcterms.abstract | Цековић, З; Токић-Вујошевић, Зорана; | |
dc.citation.issue | 13 | |
dc.citation.spage | 2028 | |
dc.citation.epage | 2034 | |
dc.citation.other | (13): 2028-2034 | |
dc.citation.rank | M22 | |
dc.identifier.wos | 000171689300021 | |
dc.identifier.doi | 10.1055/s-2001-17705 | |
dc.identifier.scopus | 2-s2.0-0034787849 | |
dc.type.version | publishedVersion |