Synthesis, Reactions and Antibacterial Activity of
3-Acetyl[1,2,4]triazolo[3,4- a ]isoquinoline Derivatives usingChitosan as Heterogeneous Catalyst under Microwave Irradiation
Hamdi M. Hassaneena, Huwaida M. E. Hassaneena, Yasmin Sh. Mohammeda, Richard M. Pagnib
aDepartment of Chemistry, Faculty of Science, Cairo University, Giza, Egypt
bDepartment of Chemistry, University of Tennessee, Knoxville, TN 37996, USA Reprint requests to Prof. Hamdi M. Hassaneen. E-mail: Hamdi 251@yahoo.com Z. Naturforsch.2011,66b,299 – 310; received December 16, 2010
3-Acetyl[1,2,4]triazolo[3,4-a]isoquinolines were prepared using chitosan as a catalyst. These com- pounds were used to prepare a novelseries of enaminones5, and their reactions with hydrazonoyl halides1and11gave triazoloisoquinolines8and13, respectively, with a carbonylpyrazole side chain.
Hydrazinolysis of8and13gave the pyrazolopyridazines10and pyrazolopyridazinones14. Reaction of5with hydroximoylhalides15led to triazoloisoquinoline16with a carbonylisoxazole side chain.
Antibacterialeffects of compounds8and10were studied.
Key words:[1,2,4]Triazolo[3,4-a]isoquinoline, Enaminones, Hydrazinolysis,
Hydrazonoyl Chlorides, Cycloaddition Reaction, Chitosan, Hydroximoyl Chloride