Catalytic synthesis of New pyrazolo [3,4-b] Pyridine via a Cooperative vinylogous anomeric-based Oxidation

Overview

Journal Sci Rep

Specialty Science

Date 2022 Aug 19

PMID 35986040

Authors

Hassan Sepehrmansourie

Mahmoud Zarei

Mohammad Ali Zolfigol

Saeed Babaee

Saeid Azizian

Sadegh Rostamnia

Affiliations

Soon will be listed here.

Abstract

In this study, a novel nano-magnetic metal-organic frameworks based on FeO namely FeO@MIL-101(Cr)-N(CHPO) was synthesized and fully characterized. The prepared sample was used as catalyst in the synthesis of pyrazolo [3,4-b] pyridines as convenient medicine by condensation reaction of aldehydes, 5-(1H-Indol-3-yl)- 2H-pyrazol-3-ylamine and 3-(cyanoacetyl)indole via a CVABO. The products were obtained with high yields at 100 °C and under solvent-free conditions.

Citing Articles

Cu(II)-Catalyzed Synthesis of Pyrazolo[3,4-]pyridine Derivatives and Their Potential Antibacterial and Cytotoxic Activities with Molecular Docking, DFT Calculation, and SwissADME Analysis.

Loganathan V, Ahamed A, Akbar I, Gerbu D, Alodaini H, Manilal A ACS Omega. 2025; 10(1):1643-1656.

PMID: 39829459 PMC: 11740132. DOI: 10.1021/acsomega.4c09524.

Supported phenylalanine on core-shell mesoporous microsphere as a catalyst for the synthesis of triazolo[1,2-a] indazole-triones and spiro triazolo[1,2-a] indazole-tetraones.

Mirheidari M, Abbas A, Safaei-Ghomi J Sci Rep. 2024; 14(1):26500.

PMID: 39489767 PMC: 11532543. DOI: 10.1038/s41598-024-78018-w.

Ti-based MOFs with acetic acid pendings as an efficient catalyst in the preparation of new spiropyrans with biological moieties.

Torkashvand Z, Sepehrmansourie H, Zolfigol M, Gu Y Sci Rep. 2024; 14(1):14101.

PMID: 38890358 PMC: 11189590. DOI: 10.1038/s41598-024-62757-x.

Design, synthesis and application of a magnetic H-bond catalyst in the preparation of new nicotinonitriles cooperative vinylogous anomeric-based oxidation.

Navazeni M, Zolfigol M, Ahmadi H, Sepehrmansourie H, Khazaei A, Hosseinifard M RSC Adv. 2024; 14(23):16607-16616.

PMID: 38779389 PMC: 11110150. DOI: 10.1039/d4ra01163e.

Synthesis of picolinates a cooperative vinylogous anomeric-based oxidation using UiO-66(Zr)-N(CHPOH) as a catalyst.

Babaee S, Sepehrmansourie H, Zarei M, Zolfigol M, Hosseinifard M RSC Adv. 2023; 13(32):22503-22511.

PMID: 37497088 PMC: 10368083. DOI: 10.1039/d3ra03438k.

References

Shiri M . Indoles in multicomponent processes (MCPs). Chem Rev. 2012; 112(6):3508-49. DOI: 10.1021/cr2003954. View

Kalhor S, Zarei M, Zolfigol M, Sepehrmansourie H, Nematollahi D, Alizadeh S . Anodic electrosynthesis of MIL-53(Al)-N(CHPOH) as a mesoporous catalyst for synthesis of novel (N-methyl-pyrrol)-pyrazolo[3,4-b]pyridines via a cooperative vinylogous anomeric based oxidation. Sci Rep. 2021; 11(1):19370. PMC: 8481481. DOI: 10.1038/s41598-021-97801-7. View

Dashteh M, Zolfigol M, Khazaei A, Baghery S, Yarie M, Makhdoomi S . Synthesis of cobalt tetra-2,3-pyridiniumporphyrazinato with sulfonic acid tags as an efficient catalyst and its application for the synthesis of bicyclic -aminocarbonitriles, cyclohexa-1,3-dienamines and 2-amino-3-cyanopyridines. RSC Adv. 2022; 10(46):27824-27834. PMC: 9055596. DOI: 10.1039/d0ra02172e. View

Dang H, Le H, Tran L, Ha H, Le H, Phan N . Copper-catalyzed one-pot domino reactions C-H bond activation: synthesis of 3-aroylquinolines from 2-aminobenzylalcohols and propiophenones under metal-organic framework catalysis. RSC Adv. 2022; 8(55):31455-31464. PMC: 9085622. DOI: 10.1039/c8ra05459b. View

Zhu L, Liu X, Jiang H, Sun L . Metal-Organic Frameworks for Heterogeneous Basic Catalysis. Chem Rev. 2017; 117(12):8129-8176. DOI: 10.1021/acs.chemrev.7b00091. View

Karimi F, Yarie M, Zolfigol M . A convenient method for synthesis of terpyridines a cooperative vinylogous anomeric based oxidation. RSC Adv. 2022; 10(43):25828-25835. PMC: 9055316. DOI: 10.1039/d0ra04461j. View

Alabugin I, Kuhn L, Medvedev M, Krivoshchapov N, A Vil V, Yaremenko I . Stereoelectronic power of oxygen in control of chemical reactivity: the anomeric effect is not alone. Chem Soc Rev. 2021; 50(18):10253-10345. DOI: 10.1039/d1cs00386k. View

Huang S, Kou X, Shen J, Chen G, Ouyang G . "Armor-Plating" Enzymes with Metal-Organic Frameworks (MOFs). Angew Chem Int Ed Engl. 2020; 59(23):8786-8798. DOI: 10.1002/anie.201916474. View

Torad N, Hu M, Ishihara S, Sukegawa H, Belik A, Imura M . Direct synthesis of MOF-derived nanoporous carbon with magnetic Co nanoparticles toward efficient water treatment. Small. 2014; 10(10):2096-107. DOI: 10.1002/smll.201302910. View

10.

Babaee S, Zarei M, Sepehrmansourie H, Zolfigol M, Rostamnia S . Synthesis of Metal-Organic Frameworks MIL-101(Cr)-NH Containing Phosphorous Acid Functional Groups: Application for the Synthesis of -Amino-2-pyridone and Pyrano [2,3-]pyrazole Derivatives via a Cooperative Vinylogous Anomeric-Based Oxidation. ACS Omega. 2020; 5(12):6240-6249. PMC: 7114146. DOI: 10.1021/acsomega.9b02133. View

11.

Li J, Kuppler R, Zhou H . Selective gas adsorption and separation in metal-organic frameworks. Chem Soc Rev. 2009; 38(5):1477-504. DOI: 10.1039/b802426j. View

12.

Pascanu V, Gonzalez Miera G, Ken Inge A, Martin-Matute B . Metal-Organic Frameworks as Catalysts for Organic Synthesis: A Critical Perspective. J Am Chem Soc. 2019; 141(18):7223-7234. DOI: 10.1021/jacs.9b00733. View

13.

Shiri M, Zolfigol M, Kruger H, Tanbakouchian Z . Bis- and trisindolylmethanes (BIMs and TIMs). Chem Rev. 2010; 110(4):2250-93. DOI: 10.1021/cr900195a. View

14.

Sepehrmansourie H, Zarei M, Zolfigol M, Babaee S, Rostamnia S . Application of novel nanomagnetic metal-organic frameworks as a catalyst for the synthesis of new pyridines and 1,4-dihydropyridines via a cooperative vinylogous anomeric based oxidation. Sci Rep. 2021; 11(1):5279. PMC: 7935861. DOI: 10.1038/s41598-021-84005-2. View

15.

Taylor K, Rieter W, Lin W . Manganese-based nanoscale metal-organic frameworks for magnetic resonance imaging. J Am Chem Soc. 2008; 130(44):14358-9. DOI: 10.1021/ja803777x. View

16.

Alhamami M, Doan H, Cheng C . A Review on Breathing Behaviors of Metal-Organic-Frameworks (MOFs) for Gas Adsorption. Materials (Basel). 2017; 7(4):3198-3250. PMC: 5453333. DOI: 10.3390/ma7043198. View

17.

Maleki A, Hajizadeh Z, Salehi P . Mesoporous halloysite nanotubes modified by CuFeO spinel ferrite nanoparticles and study of its application as a novel and efficient heterogeneous catalyst in the synthesis of pyrazolopyridine derivatives. Sci Rep. 2019; 9(1):5552. PMC: 6447565. DOI: 10.1038/s41598-019-42126-9. View

18.

Mirhosseini-Eshkevari B, Esnaashari M, Ghasemzadeh M . Novel Brönsted Acidic Ionic Liquids Confined in UiO-66 Nanocages for the Synthesis of Dihydropyrido[2,3-]Pyrimidine Derivatives under Solvent-Free Conditions. ACS Omega. 2019; 4(6):10548-10557. PMC: 6648245. DOI: 10.1021/acsomega.9b00178. View

19.

Zheng H, Zhang Y, Liu L, Wan W, Guo P, Nystrom A . One-pot Synthesis of Metal-Organic Frameworks with Encapsulated Target Molecules and Their Applications for Controlled Drug Delivery. J Am Chem Soc. 2015; 138(3):962-8. DOI: 10.1021/jacs.5b11720. View

20.

Bhanja P, Modak A, Bhaumik A . Supported Porous Nanomaterials as Efficient Heterogeneous Catalysts for CO Fixation Reactions. Chemistry. 2018; 24(29):7278-7297. DOI: 10.1002/chem.201800075. View