Melamine phosphate-modified magnetic chitosan: a novel biocompatible catalyst for the synthesis of biological tetrahydrodipyrazolopyridine and pyrazolopyranopyrimidine derivatives

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Abstract

A novel biocompatible composite was fabricated by the functionalization of magnetic chitosan with the melamine phosphate (MP) ionic compound to serve as a recoverable and bifunctional catalyst, aiming at the diversity-oriented generation of biological tetrahydropyrazolopyridine and pyrazolopyrimidine derivatives. This involved a meticulously orchestrated reaction, exploiting the in situ generated pyrazole alongside aromatic aldehydes, ammonium acetate, and (thio) barbituric acid. The present work manifests outstanding advantages, offering a novel and great method for the optimal synthesis of two valuable heterocyclic series especially five new derivatives. The resulting novel biocompatible composite was comprehensively characterized through a range of analytical techniques, including FT-IR, NH ₃ and CO ₂-TPD, XRD, TEM, FE-SEM, VSM, EDX, elemental CHNS analysis, ICP-MS, and NMR spectroscopy. Notably, the study represents a critical step in the preparation of advanced materials from accessible and cost-effective precursors.

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Recently, the synthesis of organic materials with high porosity has received considerable scientific interest, and various chemical approaches have been applied to the build-up of microporous polymer networks. In a novel catalyst-free process using Schiff base chemistry, melamine has been reacted with various di- and trivalent aldehydes to form a series of highly cross-linked microporous aminal networks with BET surface areas as high as 1377 m(2)/g and a NLDFT micropore volume of up to 0.41 cm(3)/g. It was shown that through the proper choice of the starting compounds the porosity of the final material can be fine-tuned. The materials contain up to 40 wt % of nitrogen and were also found to exhibit high thermal stability. Owing to the cheap and abundant monomers used in this study these networks are promising candidates for large-scale applications in gas storage, gas separation, catalysis, and sensing.

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Advancement on modification of chitosan biopolymer and its potential applications

Nabel A. Negm, Hassan Hefni, Ali A Abd-Elaal … (2020)

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Author and article information

Contributors

Maryam Mousavi-Ebadi: URI : https://loop.frontiersin.org/people/2671407/overviewRole: Role: Role:

Javad Safaei-Ghomi: URI : https://loop.frontiersin.org/people/2671373/overviewRole: Role: Role:

Journal

Journal ID (nlm-ta): Front Chem

Journal ID (iso-abbrev): Front Chem

Journal ID (publisher-id): Front. Chem.

Title: Frontiers in Chemistry

Publisher: Frontiers Media S.A.

ISSN (Electronic): 2296-2646

Publication date (Electronic): 15 May 2024

Publication date Collection: 2024

Volume: 12

Electronic Location Identifier: 1395008

Affiliations

Department of Organic Chemistry , Faculty of Chemistry , University of Kashan , Kashan, Iran

Author notes

Edited by: Liang-Nian He, Nankai University, China

Reviewed by: Ivaylo Tankov, Prof. Assen Zlatarov University, Bulgaria

Qing-Wen Song, Chinese Academy of Sciences (CAS), China

Ismail Ismail, University of Oregon, United States

*Correspondence: Javad Safaei-Ghomi, safaei@ 123456kashanu.ac.ir

Article

Publisher ID: 1395008

DOI: 10.3389/fchem.2024.1395008

PMC ID: 11134575

PubMed ID: 38812613

SO-VID: a05d0d30-eb0f-4225-ad3e-793062f30fc6

License:

This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.

History

Date received : 02 March 2024

Date accepted : 17 April 2024

Funding

The author(s) declare that no financial support was received for the research, authorship, and/or publication of this article.

Custom metadata

section-at-acceptance Catalytic Reactions and Chemistry

Keywords: melamine phosphate,modified magnetic chitosan,biodegradable catalyst,multicomponent reaction,pyrazole derivatives

Data availability:

Keywords: melamine phosphate, modified magnetic chitosan, biodegradable catalyst, multicomponent reaction, pyrazole derivatives

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Cited by 1

Modified magnetic chitosan with mono(6-amino-6-deoxy)-β-cyclodextrin as a novel catalyst toward the synthesis of pyrazolopyranopyrimidines and pyrano[2,3-c]pyrazole-3-carboxylates
Authors: Maryam Mousavi-Ebadi, Javad Safaei-Ghomi

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