New magnetic nanoparticle catalyst for the synthesis of pharmaceutically active tetrazolopyrimidines

Oleg M Demchuk; A Maleki; J Rahimi; A Z Wilczewska; R Jasinski

New magnetic nanoparticle catalyst for the synthesis of pharmaceutically active tetrazolopyrimidines

EuroSciCon Conference on Advanced Nanotechnology
April 18-19, 2019 | Paris, France

Oleg M Demchuk, A Maleki, J Rahimi, A Z Wilczewska and R Jasinski

Pharmaceutical Research Institute, Poland Iran University of Science and Technology, Iran University of Bialystok, Poland Institute of Organic Chemistry-Cracow University of Technology, Poland

Posters & Accepted Abstracts: Nano Res Appl

Abstract

Substituted pyrimidines are very important biologically and pharmaceutically active agents in the medicinal chemistry and drug discovery processes. A multicomponent reaction (MCRs) is ideal synthetic strategy to construct diverse molecular scaffolds of tetrazolopyrimidines starting from a few simple materials or intermediates. In connection with our continuous interest in designing new efficient and green protocols for synthesis of new biologically active compounds, we developed sonochemical approach for the one-pot four-component synthesis of 5-methyl-7-aryl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylic esters, obtained in the reaction of 2-cyano-guanidine, sodium azide, various aromatic aldehydes and methyl or ethyl acetoacetates in the presence of a catalytic amount of new functionalized hybrid organic-inorganic nanoparticle magnetic metal oxide core–shell based [1] catalyst Fe2O3@SiO2-(CH2)3NHC(O)(CH2)2PPh2.This is the first design, preparation, full characterization and application of the present nanomaterial and also the first ultrasound irradiated synthesis of the biologically and pharmaceutically important heterocyclic compounds in water used as a green solvent. The novel protocol offers several advantages such as high yields, short reaction times, mild reaction conditions, environment-friendly reaction media, easy isolation of the products, simple preparation and recoverability of the nanocatalyst by an external magnet and reusing several times without significant loss of activity. The details of our studies, which describe a scope and generality of the one-pot, simple and high atom economy strategy of synthesis of tetrazolopyrimidine derivatives with respect to various starting materials, will be presented.