Synthesis of new 5-N-pyrazolyl amino acids, pyrazolopyrimidines and pyrazolopyridines derivatives

Citation
Am. Shalaby et al., Synthesis of new 5-N-pyrazolyl amino acids, pyrazolopyrimidines and pyrazolopyridines derivatives, ACTA CHIM S, 47(2), 2000, pp. 187-203
Citations number
26
Categorie Soggetti
Chemistry
Journal title
ACTA CHIMICA SLOVENICA
ISSN journal
13180207 → ACNP
Volume
47
Issue
2
Year of publication
2000
Pages
187 - 203
Database
ISI
SICI code
1318-0207(2000)47:2<187:SON5AA>2.0.ZU;2-A
Abstract
Reaction of ketene derivatives (1a,b) on treatment with 4-amino-1-phenyl-2, 3-dimethyl pyrazolin-5-one gives compounds (2a,b) which react with hydrazin e to afford 1-phenyl-2,3 dimethyl-4-[3-(5-amino-4-substituted)-1H-pyrazolyl amino]pyrazolin-5-one (3a,b). Compounds (3a,b) on treatment with Boc. amino acids derivatives, acetic anhydride, ethyl acetoacetate and aldehydes affo rded (4a-h), (5a-h), (6-10), (11a,b), respectively. Interaction of (9) or ( 10) with acetohydrazide, hydrazines, and then with p-bromobenzaldehyde affo rded compounds (13), (14a,b) and (15), respectively. Interaction of (3a) wi th thioglycollic acid afforded pyrazolopyridines derivatives (16).