[Benzo[h][1 ,6]naphthyridines from dimethyl 1,2-dihydro-2-(2-nitrophenyl)-pyridine-3,5-dicarboxylate].
The reaction of 2-nitrobenzaldehyde with methyl propiolate and ammonium acetate in acetic acid yields 2,6-dinor-nifedipine (1a) and as a by-product not the dimethyl 2,5-dicarboxylate isomer, but the rac. 1,2-dihydropyridine (DHP) 1b, as proven by X-ray analysis. The benzo[h][1,6]naphthyridines 4-6 are synthesized from the oxidation product 2b and the photo-product 3b. The compounds 6 represent starting materials for potential anti-malarial agents.
Görlitzer
K
K
Institut für Pharmazeutische Chemie der Technischen Universität Braunschweig, Germany. k.goerlitzer@tu-bs.de
Bode
M
M
Jones
P G
PG
D000962:Antimalarials / Q000138:chemical synthesis* / Q000737:chemistry; D002264:Carboxylic Acids / Q000737:chemistry*; D018360:Crystallography, X-Ray; D007202:Indicators and Reagents; D008958:Models, Molecular; D009287:Naphthyridines / Q000138:chemical synthesis* / Q000737:chemistry; D010084:Oxidation-Reduction; D011725:Pyridines / Q000737:chemistry*
D000962:Antimalarials; D002264:Carboxylic Acids; D007202:Indicators and Reagents; D009287:Naphthyridines; D011725:Pyridines; C499895:dimethyl 1,2-dihydro-2-(2-nitrophenyl)-pyridine-3,5-dicarboxylate