[A 1-hydroxyindole-2-carboxylic acid and a 9-hydroxy-beta-carboline-4-carboxylic acid from a nifedipine analog biscyanoethyl ester].
Bis(2-cyanoethyl) 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate (3) reacts with sodium hydroxide solution to yield the 1-hydroxyindole-2-carboxylic acid 7 and the 9-hydroxy-beta-carboline-4-carboxylic acid 13. The structures of 7 and 13 were elucidated by derivatization and by spectroscopic methods. Bis(2-cyanoethyl) 2,6-dimethyl-4-(2-nitrosophenyl)pyridine-3,5-dicarboxylate (22) obtained by irradiation of 3 reacts with sodium hydroxide solution to give the cyclic hydroxamic acid 23 whose structure is proven by an independent synthesis.
Görlitzer
K
K
Institut für Pharmazeutische Chemie, Technischen Universität Braunschweig, Germany. k.goerlitzer@tu-bs.de
Baltrusch
H J
HJ
Gössnitzer
E
E
Wendelin
W
W
D002243:Carbolines / Q000138:chemical synthesis* / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D009543:Nifedipine / Q000031:analogs & derivatives* / Q000737:chemistry*; D013056:Spectrophotometry, Ultraviolet
C405583:1-hydroxyindole-2-carboxylic acid; C405584:9-hydroxycarboline-4-carboxylic acid; D002243:Carbolines; D007211:Indoles; D009543:Nifedipine