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Synthesis 2001(13): 2028-2034
DOI: 10.1055/s-2001-17705
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of New Stereoisomeric Nitrate Esters Derived from Isosorbide-Mononitrate II: Bicyclic δ-Lactams and Tetrahydrofuran Derivatives

Zorana Tokić-Vujošević a , Živorad Čeković* b
a Faculty of Pharmacy, University of Belgrade, Studentski trg 16, PO Box 158, 11000 Belgrade, Serbia, Yugoslavia
b Faculty of Chemistry, University of Belgrade, Studentski trg 16, PO Box 158, 11000 Belgrade, Serbia, Yugoslavia
e-Mail: zcekovic@chem.bg.ac.yu;
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Publication History

Received 1 March 2001
Publication Date:
11 August 2004 (online)

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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 δ-lactams, (1R,6R,7R)-N-methyl-7-endo-nitrooxy-3-oxo-5,9-dioxa-2-azabicyclo[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 δ-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.

Key words

heterocycles - nitrones - isosorbide ketonitrates - δ-lactams - Beckmann rearrangement