Synthesis of new stereoisomeric nitrate esters derived from isosorbide-mononitrate II: Bicyclic delta-lactams and tetrahydrofuran derivatives
Само за регистроване кориснике
2001
Чланак у часопису (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
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.
Кључне речи:
Beckmann rearrangement / Heterocycles / Isosorbide ketonitrates / Nitrones / δ-lactamsИзвор:
Synthesis, 2001, 13, 2028-2034Издавач:
- Georg Thieme Verlag
DOI: 10.1055/s-2001-17705
ISSN: 0039-7881
WoS: 000171689300021
Scopus: 2-s2.0-0034787849
Институција/група
PharmacyTY - JOUR AU - Tokić-Vujošević, Zorana AU - Ceković, Z PY - 2001 UR - https://farfar.pharmacy.bg.ac.rs/handle/123456789/303 AB - 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. PB - Georg Thieme Verlag T2 - Synthesis T1 - Synthesis of new stereoisomeric nitrate esters derived from isosorbide-mononitrate II: Bicyclic delta-lactams and tetrahydrofuran derivatives IS - 13 SP - 2028 EP - 2034 DO - 10.1055/s-2001-17705 ER -
@article{ author = "Tokić-Vujošević, Zorana and Ceković, Z", year = "2001", 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.", publisher = "Georg Thieme Verlag", journal = "Synthesis", title = "Synthesis of new stereoisomeric nitrate esters derived from isosorbide-mononitrate II: Bicyclic delta-lactams and tetrahydrofuran derivatives", number = "13", pages = "2028-2034", doi = "10.1055/s-2001-17705" }
Tokić-Vujošević, Z.,& Ceković, Z.. (2001). Synthesis of new stereoisomeric nitrate esters derived from isosorbide-mononitrate II: Bicyclic delta-lactams and tetrahydrofuran derivatives. in Synthesis Georg Thieme Verlag.(13), 2028-2034. https://doi.org/10.1055/s-2001-17705
Tokić-Vujošević Z, Ceković Z. Synthesis of new stereoisomeric nitrate esters derived from isosorbide-mononitrate II: Bicyclic delta-lactams and tetrahydrofuran derivatives. in Synthesis. 2001;(13):2028-2034. doi:10.1055/s-2001-17705 .
Tokić-Vujošević, Zorana, Ceković, Z, "Synthesis of new stereoisomeric nitrate esters derived from isosorbide-mononitrate II: Bicyclic delta-lactams and tetrahydrofuran derivatives" in Synthesis, no. 13 (2001):2028-2034, https://doi.org/10.1055/s-2001-17705 . .