Synthesis of 5,8-Diaryl-5,7,8,9-Tetrahydropyrimido[5,4-e]Tetrazolo[1,5-a]Pyrimidin-6(4H)-One Derivatives Catalyzed by MNPs@SiO2-Pr-AP as a New Efficient Reusable Nanomagnetic Catalyst
- 23 December 2019
- journal article
- research article
- Published by Taylor & Francis Ltd in Polycyclic Aromatic Compounds
- Vol. 41 (9), 1849-1861
- https://doi.org/10.1080/10406638.2019.1701050
Abstract
Some novel 5,8-diaryl-5,7,8,9-tetrahydropyrimido[5,4-e]tetrazolo[1,5-a]pyrimidin-6(4H)-one derivatives are prepared via one-pot reaction of aromatic aldehydes, 2-aminotetrazole and cyanoacetamide using two different types of catalytic systems including nano-magnetic catalyst supported with functionalized 4-amino-pyridine silica (MNPs@SiO2-Pr-AP) and NEt3.The highlighting points of using MNPs@SiO2-Pr-AP are easy purification, reusability of the catalyst, good yields of products with short time reactions compared with NEt3. Also the DFT calculations showed that a trans-like isomer is more stable than other possible isomers/conformers. The experimental data are also consistent with a pure compound rather than a mixture of isomers.Keywords
This publication has 28 references indexed in Scilit:
- Brønsted Acidic Ionic Liquid as an Efficient and Reusable Catalyst for One-Pot, Three-Component Synthesis of Pyrimidinone Derivatives via Biginelli-Type Reaction Under Solvent-Free ConditionsSynthetic Communications, 2011
- Mechanistic Insights on Azide−Nitrile Cycloadditions: On the Dialkyltin Oxide−Trimethylsilyl Azide Route and a New Vilsmeier−Haack-Type OrganocatalystJournal of the American Chemical Society, 2011
- Advancements in solid acid catalysts for ecofriendly and economically viable synthesis of biodieselBiofuels, Bioproducts and Biorefining, 2010
- Regioselective one-pot synthesis and anti-proliferative and apoptotic effects of some novel tetrazolo[1,5-a]pyrimidine derivativesBioorganic & Medicinal Chemistry, 2010
- Magnetic Iron Oxide Nanoparticles: Synthesis, Stabilization, Vectorization, Physicochemical Characterizations, and Biological ApplicationsChemical Reviews, 2008
- A Substituted Tetrahydro-Tetrazolo-Pyrimidine Is a Specific and Novel Inhibitor of Hepatitis B Virus Surface Antigen SecretionAntimicrobial Agents and Chemotherapy, 2007
- Magnetic Nanoparticles: Synthesis, Protection, Functionalization, and ApplicationAngewandte Chemie, 2007
- Optically Active Antifungal Azoles. XIII. Synthesis of Stereoisomers and Metabolites of 1-[(1R,2R)-2-(2,4-Difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-3-[4-(1H-1-tetrazolyl)phenyl]-2-imidazolidinone (TAK-456).CHEMICAL & PHARMACEUTICAL BULLETIN, 2001
- Multicomponent Reactions with IsocyanidesAngewandte Chemie, 2000
- Fused Tetrazolo[1,5-a]pyrimidines and 2-Azidopyrimidines from 2-Acyl-1,3-indandiones and 5-AminotetrazoleSynthesis, 1990