Investigations of the reaction mechanism concerning the formation of a 9-hydroxy-beta-carboline-4-carboxylic acid from the nifedipine analogous biscyanoethyl ester

Authors
Gorlitzer, K Baltrusch, HJ
Citation
K. Gorlitzer et Hj. Baltrusch, Investigations of the reaction mechanism concerning the formation of a 9-hydroxy-beta-carboline-4-carboxylic acid from the nifedipine analogous biscyanoethyl ester, PHARMAZIE, 55(10), 2000, pp. 747-750
Citations number
3
Categorie Soggetti
Pharmacology & Toxicology
Journal title
PHARMAZIE
ISSN journal
00317144 → ACNP
Volume
55
Issue
10
Year of publication
2000
Pages
747 - 750
Database
ISI
SICI code
0031-7144(200010)55:10<747:IOTRMC>2.0.ZU;2-9
Abstract
The 3-tert-butyl-5-methyl-1,4-dihydropyridine(DHP)-dicarboxylate 5 reacts w ith 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 correspo nding pyridine 7 and the cyclic hydroxamic acid 10. The 2-cyanoethyl-1,4-DH P-carboxylate 13, obtained from the 3-tert-butyl-5-(2-cyanoethyl)-1,4-DHP-d icarboxylate 12 by treating with TFA, reacts with sodium hydroxide solution to give the title compound 3.