Journal
APPLIED ORGANOMETALLIC CHEMISTRY
Volume 31, Issue 10, Pages -Publisher
WILEY
DOI: 10.1002/aoc.3732
Keywords
chitosan; Diels-Alder reaction; ninhydrin; pyrazolophthalazine; Schiff base
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Funding
- University of Kashan [159148/41]
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A Schiff base based on chitosan was synthesized through treatment of chitosan and p-dimethylaminobenzaldehyde in methanol solution. This biopolymeric Schiff base was used to prepare a new first row transition metal complex of Ni(II). The biopolymeric Schiff base and the synthesized tetra-coordinated complex were characterized using Fourier transform infrared, H-1 NMR and C-13 NMR techniques. Then, an efficient synthetic method for functionalized 1H-pyrazolo[1,2-b] phthalazine-5,10-diones was successfully developed using one-pot domino reaction of ninhydrin and malononitrile with 3-arylamino-5,5-dimethyl-2-cyclohexenones catalysed by the chitosan-based Schiff base complex of Ni(II) at room temperature. The advantages of this protocol are easy work-up, short reaction times and high yield of products and also the catalyst can be readily isolated from the reaction mixture and recycled without loss of catalytic activity.
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