Catalytic application of 1-(carboxymethyl)pyridinium iodide on the synthesis of pyranopyrazole derivatives

Abstract

In this investigation, acetic acid functionalized pyridinium salt, namely 1-(carboxymethyl)pyridinium iodide {[cmpy]I}, has been introduced as reusable catalyst for green, simple and efficient synthesis of 6-amino-4-(4-methoxyphenyl)-5-cyano-3-methyl-1phenyl-1,4-dihydropyrano[2,3-c]pyrazoles by the one-pot tandem four-component condensation reaction of aryl aldehydes with ethyl acetoacetate, malononitrile and hydrazine hydrate at 100 ºC under solvent-free conditions. Additionally, 1 H and 13 C NMR, mass, CHN analysis, fourier transform infrared spectroscopy (FT-IR), scanning electron microscope (SEM), thermal gravimetric analysis (TGA), differential thermal gravimetric (DTG), X-ray diffraction analysis (XRD), and calculation of crystallite size and inter planer distance of the catalyst have been investigated.

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

“…One‐pot multi‐component reactions are important in organic chemistry because of the ability of them to prepare the related products from the reaction between three or more starting materials in one step without the creation of side products and atomic waste. Short reaction time, high efficiency, simplicity, easy work up and the lack of the need to isolate the generated intermediates during the reaction are significant advantages of these reactions …”

“…Short reaction time, high efficiency, simplicity, easy work up and the lack of the need to isolate the generated intermediates during the reaction are significant advantages of these reactions. [1][2][3][4][5][6][7][8][9][10][11] 1-aminoalkyl-2-naphthols could be hydrolyzed and converted to 1-amidoalkyl-2-naphthols as a significant class of bioactive compounds. Hypotensive and bradycardia properties have been reported for 1-amidoalkyl-2-naphthols.…”

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

“…Recently, because of exploring the heterocyclic compounds in many natural products and application of them in pharmacological chemistry, researchers have done many attempts for the synthesis of similar compounds and their derivatives using by multi‐component reactions (MCRs). Multi‐component reactions (MCRs) have an important role to provide target compounds by the reaction of three or more compounds to give single product …”

Mn‐[4‐Chlorophenyl‐Salicylaldimine‐Methylpyranopyrazole]Cl2 as a Novel Nanostructured Schiff Base Complex and Catalyst

“…Recently, because of the presence of heterocyclic compounds in many natural products and their applications in pharmacological chemistry, researchers have been devoting much effort to the synthesis of similar compounds and their derivatives using multicomponent reactions (MCRs). MCRs are characterized by clean reaction conditions, high atom economy, and the combining of many complex reactions in effectively one step …”

“…MCRs are characterized by clean reaction conditions, high atom economy, and the combining of many complex reactions in effectively one step. [1][2][3][4][5][6][7][8] Schiff base compounds are widely studied as an important class of ligands due to their easy and convenient protocols of preparation and their interesting coordination chemistry. 9 Schiff base or azomethine ligands are among the principal chelating systems in bioinorganic and various related natural biological processes, and often the coordination chemistry of several forms of Schiff bases is studied extensively.…”