A new inorganic–organic hybrid material Al-SBA-15-TPI/H₆P₂W₁₈O₆₂ catalyzed one-pot, three-component synthesis of 2H-indazolo[2,1-b]phthalazine-triones

Abstract

A new inorganic-organic hybrid material Al-SBA-15-TPI/H6P2W18O62 was prepared and fully characterized by SEM, XRD, FT-IR, TGA-DTA, and UV-Vis spectroscopic techniques. Then, the prepared nanomaterial was used as a simple, cost-effective, and reusable heterogeneous catalyst for the synthesis of 2H-indazolo[2,1-b]phthalazine-1,6,11(13H)-trione derivatives by a one-pot, three-component condensation reaction of phthalhydrazide, cyclic diones, and aromatic aldehydes under solvent free conditions at 100 °C in a short time. This methodology has proven to be efficient and environmentally benign in terms of high yields and low reaction times and offers significant improvements with regard to the scope of transformation and simplicity of operation by avoiding expensive or corrosive catalysts.

A magnetically-separable H 3 PW 12 O 40 @Fe 3 O 4 /EN-MIL-101 catalyst for the one-pot solventless synthesis of 2H-indazolo[2,1- b ] phthalazine-triones

“…Among the investigated diketones (Table 1), dimedone (5,5-dimethyl-1,3-cyclohexane-dione) gave the highest product yield. The electron releasing nature of the two methyl substituents in dimedone appears desirable to activate the diketone for this condensation reaction [65,66]. The linear hexanediones (2, 5-hexane-dione and 3, 4-hexane-dione) were less efficient than their cyclic counterpart, resulting in lower product yields of 52-69 % after 40 min.…”

“…Yields refer to the isolated pure products. The desired pure products were characterized by comparison of their physical data with those of known compounds [65].…”

“…The catalyst activity was interpreted by donating H + from the heteropolyacid and Lewis acid sites on Fe3O4 and MIL101fragments which was initially bound to the carbonyl oxygen of the aldehyde. Finally, (I) was generated by nucleophilic addition of dimedone to the carbonyl group of aldehyde and provoked by loss of H2O which affords (II) [65,73]. …”

Silica coated magnetic NiFe2O4 nanoparticle supported phosphomolybdic acid; synthesis, preparation and its application as a heterogeneous and recyclable catalyst for the one-pot synthesis of tri- and tetra-substituted imidazoles under solvent free conditions

“…42 Thus, in this study, an efficient magnetic supported acid catalyst (NFS-PMA) was prepared by the chemical supporting of Keggin HPAs onto silica coated NiFe 2 O 4 MNPs (Scheme 1). This strategy enabled research groups to overcome the limitations involved in the separation and recycling of homogeneous catalysts.…”

Deep eutectic solvent an efficient reaction medium for the synthesis of chromeno pyrazolo and indazolo phthalazine derivatives

“…Chromeno pyrazolo and indazolo phthalazine derivatives constitute a bridgehead hydrazine as a group of nitrogen‐containing heterocyclic compounds, which possess a multiplicity of pharmacological properties including anti‐inflammatory, antimicrobial, antifungal, anticonvulsant, vasorelaxant, antitumor and cardiotonic activities . Due to the large biological activity of phthalazine compounds, number of methods have been reported such as ionic liquids, magnetic nanoparticles, solid supported catalysts, heteropolyacids, β‐cyclodextrin, microwave, sulfonic acid, alumina nanoparticles and p‐TSA …”