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Inorganic–organic hybrid chitosan‐based Schiff base–Ni complex as a novel, highly efficient and recyclable heterogeneous catalyst for synthesis of pyrazolophthalazinediones
Author(s) -
Naeimi Hossein,
Lahouti Sepideh
Publication year - 2017
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.3732
Subject(s) - chemistry , schiff base , malononitrile , chitosan , catalysis , ninhydrin , yield (engineering) , methanol , organic chemistry , polymer chemistry , nuclear chemistry , combinatorial chemistry , metallurgy , biochemistry , amino acid , materials science
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, 1 H NMR and 13 C NMR techniques. Then, an efficient synthetic method for functionalized 1 H –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.