Generation of hazardous methyl azide and its application to synthesis of a key-intermediate of picarbutrazox, a new potent pesticide in flow.

Bioorg Med Chem

Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto 615-8510, Japan. Electronic address:

Published: December 2017

Generation and reactions of methyl azide (MeN) were successfully performed by using a flow reactor system, demonstrating that the flow method serves as a safe method for handling hazardous explosive methyl azide. The reaction of NaN and MeSO in a flow reactor gave a MeN solution, which was used for Huisgen reaction with benzoyl cyanide in a flow reactor after minimal washing. The resulting 1-methyl-5-benzoyltetrazole serves as a key intermediate of picarbutrazox (IX), a new potent pesticide.

Download full-text PDF

Source
http://dx.doi.org/10.1016/j.bmc.2017.07.005DOI Listing

Publication Analysis

Top Keywords

methyl azide
12
flow reactor
12
picarbutrazox potent
8
potent pesticide
8
flow
5
generation hazardous
4
hazardous methyl
4
azide application
4
application synthesis
4
synthesis key-intermediate
4

Similar Publications

Nowadays, nucleic acid derivatives capable of modulating gene expression at the RNA level have gained widespread recognition as promising therapeutic agents. A suitable degree of biological stability of oligonucleotide therapeutics is required for in vivo application; this can be most expeditiously achieved by the chemical modification of the internucleotidic phosphate group, which may also affect their cellular uptake, tissue distribution and pharmacokinetics. Our group has previously developed a strategy for the chemical modification of the phosphate group via the Staudinger reaction on a solid phase of the intermediate dinucleoside phosphite triester and a range of, preferably, electron deficient organic azides such as sulfonyl azides during automated solid-phase DNA synthesis according to the conventional β-cyanoethyl phosphoramidite scheme.

View Article and Find Full Text PDF

The well-known inhibitory strength of 3d metal Schiff base complexes against urease enzymes has long been acknowledged, but their untapped potential to act as ureolytic mimics of active metallobiosites remained unexplored. To break the new ground, we present pyrrolidine-based mononuclear Ni(II)-azide complex {[NiL(HL)(N)]·1.5(HO)} using the N,N,O donor ligand, namely ()-4-bromo-2-(((2-(pyrrolidin-1-yl)ethyl)imino)methyl)phenol.

View Article and Find Full Text PDF

Nanocomposite materials composed of an organic matrix and an inorganic nanofiller have been the subject of intense research in recent years. Indeed, the synergy between these two phases confers improved properties thanks to an increased surface-volume ratio, which reinforces the interactions between the particles and the polymer matrix. These interactions depend on many factors such as the shape, size and dispersion of the nanoobjects.

View Article and Find Full Text PDF

Synthesis of 1,2,3-Triazole-Methyl-Menadione Derivatives: Evaluation of Electrochemical and Antiparasitic Properties against two Blood-Dwelling Parasites.

ChemMedChem

December 2024

Laboratoire d'Innovation Moléculaire et Applications (LIMA), Team Bio(IN)organic & Medicinal Chemistry, UMR7042 CNRS-Université de Strasbourg-Université Haute-Alsace, European School of Chemistry, Polymers and Materials (ECPM), 25, rue Becquerel, F-67087, Strasbourg, France.

This study explores the synthesis and evaluation of novel 1,2,3-triazole-methyl-1,4-naphthoquinone hybrids, focusing on their electrochemical properties and antiparasitic efficacies against two human blood-dwelling parasites Plasmodium falciparum and Schistosoma mansoni. Using copper-catalyzed azide-alkyne cycloaddition (CuAAC), a well-established tool in click chemistry, two synthetic routes were assessed to develop α- and β-[triazole-methyl]-menadione derivatives. By optimizing the CuAAC reaction conditions, yields were significantly improved, reaching up to 94 % for key intermediates and resulting in the formation of a library of approximately 30 compounds.

View Article and Find Full Text PDF

Designing Phenolphthalein-Based Adsorptive Membranes for the High-Affinity, High-Capacity Capture of Contaminants from Water.

ACS Appl Mater Interfaces

December 2024

Department of Chemical and Biomolecular Engineering, University of Notre Dame, Notre Dame, Indiana 46556, United States.

The selective removal of solutes is crucial for ensuring a sustainable water supply, recovering resources, and cost-effective biomanufacturing. Adsorptive membranes are promising in this regard due to their rapid mass transfer and low energy demands. However, state-of-the-art adsorptive membranes offer limited pore sizes and surface chemistries.

View Article and Find Full Text PDF

Want 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!