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Efficient Regioselective Synthesis and Potential Antitumor Evaluation of Isoxazolo[5,4‐ b ]pyridines and Related Annulated Compounds
Author(s) -
Hamama Wafaa S.,
Ibrahim Mona E.,
Zoorob Hanafi H.
Publication year - 2012
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.201100258
Subject(s) - chemistry , dimedone , oxazolone , annulation , regioselectivity , benzaldehyde , quinoline , pyridine , azine , pyrazolone , thiazole , derivative (finance) , organic chemistry , stereochemistry , medicinal chemistry , catalysis , financial economics , economics
The reaction of 5‐amino‐3‐methylisoxazole with appropriate α,β‐unsaturated ketones gave the corresponding isoxazolo[5,4‐ b ]pyridines. Treatment of 1 with 2,6‐dibenzylidenecyclohexanone or 2‐benzylidenedimedone afforded the corresponding isoxazolo[5,4‐ b ]quinoline derivatives. 4,6,8,9‐Tetrahydroisoxazolo[5,4‐ b ]quinolin‐5‐one derivative was also obtained by multicomponent condensation reaction of 1 with dimedone and benzaldehyde. Heterocyclic annulation of the isoxazolo[5,4‐ b ]pyridine system was achieved via reaction of 1 with benzylidene derivatives of indandione, quinuclidone, pyrazolone, and oxazolone. A representative of some newly synthesized compounds was evaluated as antitumor agents.