Catalytic Applications of Nano‐Fe‐[Phenyl‐Salicylaldimine‐Methylpyranopyrazole]Cl₂ as a Schiff Base Complex and Nanostructured Catalyst for the Synthesis of Hexahydroquinolines

Abstract

By the four‐component condensation reaction of benzaldehyde with ethyl acetoacetate, malononitrile, and hydrazine hydrate using FeCl2, a pyranopyrazole derivative was synthesized and then reacted with salicylaldehyde to give nano‐Fe‐[phenyl‐salicylaldimine‐methylpyranopyrazole]Cl2 (nano‐[Fe‐PSMP]Cl2). The prepared nano‐Schiff base complex was successfully used as an efficient catalyst for the synthesis of hexahydroquinolines.

Design and identification of nano‐Mg‐[4‐methoxy phenyl‐salicylaldimine–methyl‐pyranopyrzole] Cl2 and its catalytic application on the preparation of 1‐(α‐aminoalkyl)‐2‐naphthols

“…For the synthesis of nano‐Mg‐[4‐methoxy phenylsalicylaldiminemethylpyranopyrazole]Cl 2 (nano‐[Mg‐4MSMP]Cl 2 ), firstly, 4‐methoxybenzaldehyde was reacted with ethyl acetoacetate, malononitrile and hydrazine hydrate to afford the related pyranopyrazole according to previous literature . In the next step, the prepared amine was reacted with salicylaldehyde and MgCl 2 .6H 2 O to give nano‐Mg‐[4‐methoxy phenylsalicylaldiminemethylpyranopyrazole]Cl 2 (nano‐[Mg‐4MSMP]Cl 2 ) as a nano‐Schiff base complex (Scheme ).…”

“…Additionally, Schiff base complexes were used as efficient catalysts in organic transformations . In continuing our previous works to prepare some new Schiff base complexes by the reaction of pyranopyrazole derivatives with salicylaldehyde and different metal salts, herein, we have designed and identified nano‐Mg‐[4‐methoxy phenylsalicylaldiminemethylpyranopyrazole]Cl 2 (nano‐[Mg‐4MSMP]Cl 2 ) (Figure ) and used it, as an active and efficient catalyst, for the preparation of 1‐(α‐aminoalkyl)‐2‐naphthol derivatives (Scheme ).…”

Nano‐Zn[2‐boromophenylsalicylaldiminemethylpyranopyrazole]Cl2 as a novel nanostructured Schiff base complex and catalyst for the synthesis of pyrano[2,3‐d]pyrimidinedione derivatives

“…Water was added to the reaction mixture to dissolve isonicotinic acid and the aqueous layer was separated from the reaction mixture. Then, the solid residue (crude product) was triturated by a mixture of ethanol and water (19/1) to 6‐amino‐4‐(2‐bromophenyl)‐3‐methyl‐2,4‐dihydropyrano[2,3‐ c ]pyrazole‐5‐carbonitrile as an amine product . The prepared amine (1 mmol) and ZnCl 2 (1 mmol) were pulverized in a mortar for 10 min and then transferred to a 25 ml round‐bottomed flask containing salicylaldehyde (1.5 mmol), connected to a reflux condenser and stirred at 120 °C for 72 h. After this time, the reaction mixture was washed three times with ethyl acetate and hexane (9/1) to purify nano‐[Zn‐2BSMP]Cl 2 from excess salicylaldehyde.…”

“…Also, they have been introduced as catalysts for the preparation of various organic compounds . Recently, we have reported a new category of Schiff base obtained by the reaction of pyranopyrazole derivatives with salicylaldehyde and various metal salts . In the work reported herein, in continuation of our previous investigations, we prepared and characterized nano‐Zn[2‐boromophenylsalicylaldiminemethylpyranopyrazole]Cl 2 (nano‐[Zn‐2BSMP]Cl 2 ; Figure ) and used it as an effective catalyst for the preparation of pyrano[2,3‐ d ]pyrimidinediones (Scheme ).…”

Synthesis of 4‐((2‐hydroxynaphthalen‐1‐yl)(aryl)methyl)‐5‐methyl‐2‐phenyl‐1H‐pyrazol‐3(2H)‐ones using nano‐Zn‐[2‐boromophenyl‐salicylaldimine‐methylpyranopyrazole]Cl2 nanoparticles

“…Schiff base compounds are widely introduced as one of the important groups of ligands because of their easy and convenient protocols for the synthesis and their interesting coordination chemistry . Lately, we have prepared and identified a new category of Schiff base complexes by the reaction of pyranopyrazole derivatives with salicylaldehyde and different metal salts . Herein, in continuing our previous investigations, we have prepared and characterized nano‐Zn‐[2‐boromophenyl‐salicylaldimine‐methylpyranopyrazole]Cl 2 (nano‐[Zn‐2BSMP]Cl 2 ) and applied it, as an active complex and effective catalyst, for the synthesis of 4‐((2‐hydroxynaphthalen‐1‐yl)(aryl)methyl)‐5‐methyl‐2‐phenyl‐1H‐pyrazol‐3(2H)‐ones (Scheme ).…”