» Articles » PMID: 34020696

Nano-SiO/DBN: an Efficacious and Reusable Catalyst for One-pot Synthesis of Tetrahydrobenzo[b]pyran Derivatives

Overview
Journal BMC Chem
Publisher Springer Nature
Specialty Chemistry
Date 2021 May 22
PMID 34020696
Citations 6
Authors
Affiliations
Soon will be listed here.
Abstract

Background: The nano-sized particles enhance the exposed surface area of the active part of the catalyst, thereby increasing the contact between precursors and catalyst considerably. In this study, nano-SiO/1,5-diazabicyclo[4.3.0]non-5-en was synthesized, characterized and used as a heterogeneous nanocatalyst for the synthesis of tetrahydrobenzo[b]pyran derivatives. Fourier Transform Infrared Spectroscopy, Field Emission Scanning Electron Microscopy, Brunauer-Emmett-Teller plot, Energy Dispersive X-ray Spectroscopy and Thermo Gravimetric Analysis were used to discern nano-SiO/1,5-diazabicyclo[4.3.0]non-5-en.

Results: Tetrahydrobenzo[b]pyrans were synthesized by using nano-SiO/1,5-diazabicyclo[4.3.0]non-5-en via one-pot three-component condensation of malononitrile, aldehydes and dimedone in HO/EtOH at 60 °C. The results indicate that tetrahydrobenzo[b]pyrans were synthesized in good to high yields and short reaction times.

Conclusions: The fundamental privileges of this method are short reaction time, plain procedure, recyclability of catalyst and high yields of products.

Citing Articles

Nanao/organocatalyat SiO/4-(2-Aminoethyl)-morpholine as a new, reusable, and efficacious catalyst for the synthesis of polyhydroquinolines derivatives and antibacterially active evaluation.

Amiri-Zirtol L, Karimi Z, Farahbakhsh J, Gholami A, Abootalebi S BMC Chem. 2025; 19(1):58.

PMID: 40033314 PMC: 11874776. DOI: 10.1186/s13065-025-01403-7.


L-Aspartic acid-functionalized magnetic nanoparticles: as a new magnetically reusable bifunctional acid-base catalysts for the synthesis of benzo[b]pyran and pyrano[3,2-c] chromene derivatives.

Amiri-Zirtol L, Mostashfi H, Sabet R, Karimi Z, Ranjbar-Karimi R Sci Rep. 2025; 15(1):248.

PMID: 39747901 PMC: 11697017. DOI: 10.1038/s41598-024-71901-6.


A facile one-pot synthesis of tetrahydrobenzo[]pyrans and 2-amino-4-chromenes under green conditions.

Momeni S, Ghorbani-Vaghei R RSC Adv. 2024; 14(30):21608-21622.

PMID: 39015477 PMC: 11249666. DOI: 10.1039/d4ra04239e.


A new role for concentrated solar radiation (CSR) as a renewable heat source for the catalyst-solvent free synthesis of tetrahydrobenzo[b]pyran scaffolds.

Mohamadpour F Sci Rep. 2023; 13(1):11485.

PMID: 37460799 PMC: 10352380. DOI: 10.1038/s41598-023-38662-0.


FeO@nano-almondshell/Si(CH)/2-(1-piperazinyl)ethylamine as an effective magnetite almond shell-based nanocatalyst for the synthesis of dihydropyrano[3,2-c]chromene and tetrahydrobenzo[b]pyran derivatives.

Mallah D, Mirjalili B, Bamoniri A Sci Rep. 2023; 13(1):6376.

PMID: 37076551 PMC: 10115822. DOI: 10.1038/s41598-023-33286-w.


References
1.
Domling A, Wang W, Wang K . Chemistry and biology of multicomponent reactions. Chem Rev. 2012; 112(6):3083-135. PMC: 3712876. DOI: 10.1021/cr100233r. View

2.
CHYLINSKA J, URBANSKI T . DIHYDRO-1,3-OXAZINE DERIVATIVES AND THEIR ANTITUMOR ACTIVITY. J Med Chem. 1963; 6:484-7. DOI: 10.1021/jm00341a004. View

3.
Singh P, Yadav P, Mishra A, Awasthi S . Green and Mechanochemical One-Pot Multicomponent Synthesis of Bioactive 2-amino-4-benzo[]pyrans via Highly Efficient Amine-Functionalized SiO@FeO Nanoparticles. ACS Omega. 2020; 5(8):4223-4232. PMC: 7057680. DOI: 10.1021/acsomega.9b04117. View

4.
Shaabani A, Amini M, Ghasemi S, Ghadari R, Rezayan A, Fazaeli Y . Pyridine-functionalized MCM-41 as an efficient and recoverable catalyst for the synthesis of pyran annulated heterocyclic systems. Chem Pharm Bull (Tokyo). 2010; 58(2):270-2. DOI: 10.1248/cpb.58.270. View

5.
Bisht S, Jaiswal N, Sharma A, Fatima S, Sharma R, Rahuja N . A convenient synthesis of novel pyranosyl homo-C-nucleosides and their antidiabetic activities. Carbohydr Res. 2011; 346(10):1191-201. DOI: 10.1016/j.carres.2011.03.006. View