We show the ability of a nitrilimine prepared from 3-amino-5-nitro-1,2,4-triazole to undergo various cyclization and rearrangement reactions, giving a beautiful diversity of nitrogen-rich heterocyclic products. This chemistry includes the first cyclization of a nitrilimine with a diazonium species, giving a tetrazole, a previously unknown transformation, as well as leading to the creation of several new energetic materials with backbones not available by traditional techniques. New materials prepared were characterized both chemically (multinuclear NMR, IR, mass spectrometry, and elemental analysis) and energetically, with sensitivities and performances reported.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.inorgchem.1c00469 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
1,3-Dipolar Cycloaddition of Nitrile Oxides and Nitrilimines to (-)-β-Caryophyllene: Stereoselective Synthesis of Polycyclic Derivatives and Their Biological Testing.
Int J Mol Sci
October 2024
Department of Chemistry, M. V. Lomonosov Moscow State University, 119991 Moscow, Russia.
The cycloaddition of nitrile oxides and nitrilimines to one or both of the C=C double bonds of caryophyllene is described. The possibility of introducing five-membered fused and spiro-linked heterocycles into the structure of sesquiterpenes by the 1,3-dipolar cycloaddition reactions of nitrile oxides and nitrilimines to caryophyllene was demonstrated. As a result of these reactions, pharmacophore fragments of isoxazoline and pyrazoline are introduced into the structure of caryophyllene, which leads to an increase in the conformational rigidity of the molecule.
View Article and Find Full Text PDFA quantum mechanistic investigation into the unusual reactions of nitrilimine and nitrile oxide with 2,3,4,5-tetraphenylcyclopentadienone.
J Mol Model
July 2024
Theoretical and Computational Chemistry Laboratory, Department of Chemistry, Kwame Nkrumah University of Science and Technology, Kumasi, Ghana.
Context: The theoretical study investigates the [3 + 2] cycloaddition (32CA) reactions between C, N-diphenyl nitrilimine with 2,3,4,5-tetraphenylcyclopentadienone and benzonitrile oxide with 2,3,4,5-tetraphenylcyclopentadienone. Nitrilimines and nitrile oxides are dipoles used in the synthesis of several heterocyclic compounds, including spiropyrazoline oxindoles and isoxazolines. The derivatives of these compounds are found with different biological activities, such as ion channel blockers, anti-inflammatory and anticancer agents as well as antimalarial.
View Article and Find Full Text PDFHeterocyclic Nitrilimines and Their Use in the Synthesis of Complex High-Nitrogen Materials.
Inorg Chem
June 2021
Department of Materials Engineering, Purdue University, 205 Gates Road, West Lafayette, Indiana 47906, United States.
We show the ability of a nitrilimine prepared from 3-amino-5-nitro-1,2,4-triazole to undergo various cyclization and rearrangement reactions, giving a beautiful diversity of nitrogen-rich heterocyclic products. This chemistry includes the first cyclization of a nitrilimine with a diazonium species, giving a tetrazole, a previously unknown transformation, as well as leading to the creation of several new energetic materials with backbones not available by traditional techniques. New materials prepared were characterized both chemically (multinuclear NMR, IR, mass spectrometry, and elemental analysis) and energetically, with sensitivities and performances reported.
View Article and Find Full Text PDFSynthesis of 1,3,4-Thiadiazoles and 1,4,2-Oxathiazoles from α-Enolic Dithioesters and Active 1,3-Dipoles.
J Org Chem
April 2021
Institute of Marine Biomedicine/Hoffmann Institute of Advanced Materials, Shenzhen Polytechnic, Shenzhen 518055, China.
The synthesis of two kinds of five-membered organosulfur heterocycles (i.e., 1,4,2-oxathiazoles and 1,3,4-thiadiazoles) from α-enolic dithioesters with active 1,3-dipoles (nitrile oxides and nitrilimines) generated in situ was achieved under mild reaction conditions.
View Article and Find Full Text PDFUnveiling the molecular mechanisms of the cycloaddition reactions of aryl hetaryl thioketones and C,N-disubstituted nitrilimines.
J Mol Model
February 2021
Center for Molecular Quantum Chemistry Research, Department of Basic and Computational Sciences, Koachie Health Systems, Accra, Ghana.
Many synthetic routes to constructing biologically active heterocyclic compounds are made feasible through the (3 + 2) cycloaddition (32CA) reactions. Due to a large number of possible combinations of several heteroatoms from either the three-atom components (TACs) or the ethylene derivatives, the potential of the 32CA reactions in heterocyclic syntheses is versatile. Herein, the cycloaddition reaction of thiophene-2-carbothialdehyde derivatives and C,N-disubstituted nitrilimines have been studied through density functional theory (DFT) calculations at the B3LYP/6-311G(d,p) level of theory.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!