Nano–Mn‐[4‐nitrophenyl‐salicylaldimine‐methyl pyranopyrazole]Cl₂ as a new nanostructured Schiff base complex and catalyst for the synthesis of hexahydroquinolines

Abstract

By the reaction of 4-nitrobenzaldehyde with ethyl acetoacetate, malononitrile and hydrazine hydrate, pyranopyrazole derivative as an active biological compound was synthsized and then reacted with salicylaldehyde and MnCl 2 .4H 2 O to afford nano-Mn-[4-nitrophenyl-salicylaldimine-methyl pyranopyrazole]Cl 2 (nano-[Mn-4NSMP]Cl 2 ) for the first time. The produced Schiff base complex with nanostructured was fully characterized by Fourier transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), thermal gravimetric analysis (TGA), differential thermal gravimetric (DTG) and scanning electron microscope (SEM) and used it as an efficient catalyst for the preparation 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 ).…”

“…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. [29][30][31][32][33] In the next step, the prepared amine was reacted with salicylaldehyde and MgCl 2 . [2,3-c]pyrazole-5-carbonitrile (4MSMP) as a Schiff base was prepared alone and its structure was studied by 1 HNMR and 13 CNMR spectra as well as mass analysis.…”

Preparation and characterization of Cu (II) supported on poly(8‐hydroxyquinoline‐p‐styrene sulphonate) and its application as catalyst for the synthesis of hexahydroquinolines

“…This part of quinoline derivatives has very usages in medicinal chemistry, being used as antiasthamatic, antibacterial antihypertensive, anti‐inflammatory, antimalarial, and tyrosine kinase inhibiting compounds . One of the categories of dihydropyridines (DHPs) with a modified structural scaffold is hexahydroquinolines (HHQs) which could be obtained through Hantzsch synthesis by the one‐pot four‐component condencation reaction of various aromatic aldehydes with dimedone, β ‐ketoesters and ammonium acetate in the presence of various catalysts such as silica‐bonded imidazolium‐sulfonic acid chloride, nano‐Fe 3 O 4 , 1,3‐disulfonic acid imidazolium hydrogen sulfate, nano‐Mn‐[4‐nitrophenyl‐salicylaldimine‐methyl pyranopyrazole]Cl 2 …”

“…[16,17] One of the categories of dihydropyridines (DHPs) with a modified structural scaffold is hexahydroquinolines (HHQs) which could be obtained through Hantzsch synthesis by the one-pot four-component condencation reaction of various aromatic aldehydes with dimedone, β-ketoesters and ammonium acetate in the presence of various catalysts such as silica-bonded imidazolium-sulfonic acid chloride, [17] nano-Fe 3 O 4 , [18] 1,3-disulfonic acid imidazolium hydrogen sulfate, [19] nano-Mn-[4-nitrophenyl-salicylaldimine-methyl pyranopyrazole]Cl 2 . [20] In continuation of our previous research on developing of Cu (II) supported on polymer, [21] herein, initially, Cu (II) was loaded onto the structure of the prepared poly(8-hydroxyquinoline-p-styrenesulfonate), and then used as catalyst for the preparation of hexahydroquinolines (Schemes 1 and 2).…”

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

“…[8][9][10][11][12][13] Hexahydroquinolines (HHQs) can be prepared by the condensation reaction of various aromatic aldehydes, dimedone, β-ketoesters, and ammonium acetate via the one-pot multicomponent condensation reaction using different catalysts. [14][15][16][17][18][19][20][21][22][23][24] Because of the important properties of these compounds, and in continuation of our studies in the preparation of nano-Schiff base complexes, [24][25][26] we report here the synthesis of nano-Fe-[phenyl-salicylaldimine-methylpyranopyrazole]Cl 2 (nano-[Fe-PSMP]Cl 2 ) as an active complex and efficient catalyst for the preparation of hexahydroquinolines (Scheme 1).…”