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Updated: Aug 26, 2026

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
[Benzo[c][2,7]naphthyridines from 2,6-dinor-nifedipine and its dimethyl 2,5-dicarboxylate isomer]
K Görlitzer1, M Bode, P Frohberg
1Institut für Pharmazeutische Chemie der Technischen Universität Braunschweig, Germany. k.goerlitzer@tu-bs.de
Abstract:
The reaction of 2-nitrobenzaldehyde with methyl propiolate and ammonium acetate in acetic acid yields 2,6-dinor-nifedipine (1a) and the isomeric rac. 1,4-dihydropyridine (DHP) 1b. The DHP 1 are dehydrogenated both chemically and by anodic oxidation using a rotating platinum electrode (RPE) by means of differential pulse voltammetry (DPV) affording the corresponding pyridines 2a, b. Compound 1a is more stable, while compound 1b is less stable than nifedipine. Irradiation of the DHP 1 with UV-A light forms the nitrosophenyl-pyridines 3, which cyclize after addition of conc. hydrochloric acid to yield the chloro substituted hydroxamic acids 4a, b. The hydroxamic acids 4c, d are obtained treating 2a, b with zinc in acetate buffer pH 4.6. The hydroxamic acids 4b, d demonstrate only a moderate inhibition of 5-lipoxygenase (5-LOX) of human whole blood compared with the activity of the reference compound zileutone. The formation of 15-HETE is also inhibited. Compound 4a reduces the activity of cyclooxygenase. The lactames 5, obtained from the hydroxamic acids 4 by desoxygenation with phosphorus trichloride, react with phosphoryl chloride to give compounds 6, representing educts for potential agents against malaria.
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