A novel sulfamic acid functionalized nano-catalyst on the basis of calixresorcinarene for the green one-pot synthesis of 2H-indazolo[2,1-b]phthalazine-triones under thermal solvent-free conditions
- 105 Downloads
N-propyl sulfamic acid supported nano-catalyst on the basis of calixresorcinarene was prepared via the efficient and facile reaction of amine functionalized polycalixresorcinarene with chlorosulfonic acid. The achieved catalytic system was characterized using some spectroscopic techniques such as Fourier transform Infrared (FT-IR) spectroscopy, field emission scanning electron microscopy (FE-SEM), transmission electron microscopy (TEM), and CHNS elemental analysis. This newly developed acidic catalyst was employed efficiently in a one-pot three-component condensation reaction of aromatic aldehydes, dimedone and phthalhydrazide for the synthesis of 2H-indazolo[2,1-b]phthalazine-trione derivatives through an easy and eco-friendly methodology. The catalyst was easily separated from the reaction mixture by simple filtration and the desired products were achieved in good to excellent yields in short reaction times.
KeywordsN-propyl sulfamic acid functionalized nano-catalyst Heterogeneous catalysis Multi-component reactions Solvent-free One-pot condensation 2H-indazolo[2,1-b]phthalazine-triones
This work was supported by the Research Council at the University of Shahid Chamran.
- 1.Anastas PT, Warner JC (1998) Green chemistry: theory and practice. Oxford University, OxfordGoogle Scholar
- 15.El-Sakka SS, Soliman AH, Imam AM (2009) Synthesis, antimicrobial activity and electron impact of mass spectra of phthalazine-1,4-dione derivatives. Afinidad 66:167–172Google Scholar
- 16.Singh S, Yadav A, Meena AK, Singh U, Singh B, Gaurav A, Rao MM, Panda P, Singh R (2010) Pharmacological action and SAR of phthalazine derivatives. Int J Chem Anal Sci 1:79–87Google Scholar
- 28.Shaterian HR, Hosseinian A, Ghashang M (2009) Reusable silica supported poly phosphoric acid catalyzed three-component synthesis of 2H-indazolo[2,1-b]phthalazine-trione derivatives. Arkivoc 2:59–67Google Scholar
- 42.Mouradzadegun A, Elahi S, Abadast F (2014) Synthesis of a 3D-network polymer supported Bronsted acid ionic liquid based on calix-resorcinarene via two post-functionalization steps: a highly efficient and recyclable acid catalyst for the preparation of symmetrical bisamides. RSC Adv 4:31239–31248CrossRefGoogle Scholar
- 50.Mirhosseini-Eshkevari B, Ghasemzadeh MA, Safaei-Ghomi J (2015) An efficient and green one-pot synthesis of indazolo[1,2-b]-phthalazinetriones via three-component reaction of aldehydes, dimedone, and phthalhydrazide using Fe3O4@SiO2 core-shell nanoparticles. Res Chem Intermed 41:7703–7714CrossRefGoogle Scholar