[The reaction mechnism for formation of a 9-hydroxy-beta-carbolin-4-carboxylic acid from the nifedipine analogue biscyanoethyl ester].
The 3-tert-butyl-5-methyl-1,4-dihydropyridine(DHP)-dicarboxylate 5 reacts with trifluoroacetic acid (TFA) by elimination of the tert-butylester group yielding the 1,4-DHP 6. Irradiation of 6 by UV-A-light affords the corresponding pyridine 7 and the cyclic hydroxamic acid 10. The 2-cyanoethyl-1,4-DHP-carboxylate 13, obtained from the 3-tert-butyl-5-(2-cyanoethyl)-1,4-DHP-dicarboxylate 12 by treating with TFA, reacts with sodium hydroxide solution to give the title compound 3.
Görlitzer
K
K
Institut für Pharmazeutische Chemie, Technischen Universität Braunschweig, Germany. k.goerlitzer@tu-bs.de
Baltrusch
H J
HJ
D002243:Carbolines / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D009543:Nifedipine / Q000031:analogs & derivatives / Q000737:chemistry*; D014466:Ultraviolet Rays
C418209:1,4-dihydro-2,6--dimethyl-4-(2-nitrophenyl)-3,5-pyridinedicarboxylic acid bis(2-cyanoethyl) ester; C418210:9-hydroxy-1,3-dimethyl-9H-beta-carboline-4-carboxylic acid; D002243:Carbolines; D009543:Nifedipine