Green in water sonochemical synthesis of tetrazolopyrimidine derivatives by a novel core-shell magnetic nanostructure catalyst |
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Institution: | 1. Catalysts and Organic Synthesis Research Laboratory, Department of Chemistry, Iran University of Science and Technology, Tehran 16846-13114, Iran;2. Department of Organic Chemistry, Maria Curie-Sklodowska University, Gliniana 33, Lublin 20-614, Poland;3. Institute of Chemistry, University of Białystok, Ciołkowskiego 1K, 15-245 Białystok, Poland;4. Institute of Organic Chemistry and Technology, Cracow University of Technology, Warszawska 24, Cracow, Poland |
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Abstract: | A green approach for the one-pot four-component sonochemical synthesis of 5-methyl-7-aryl-4,7-dihydrotetrazolo1,5-a]pyrimidine-6-carboxylic esters from the reaction of 2-cyano-guanidine, sodium azide, various aromatic aldehydes and methyl or ethyl acetoacetate in the presence of a catalytic amount of Fe2O3@SiO2-(CH2)3NHC(O)(CH2)2PPh2 as a new hybrid organic–inorganic core–shell nanomagnetic catalyst is described. This is the first design, preparation, characterization and application of the present nanomaterial and also the first ultrasound irradiated synthesis of the biologically and pharmaceutically important heterocyclic compounds in water as a green solvent. This novel sonocatalysis/nanocatalysis protocol offers several advantages such as high yields, short reaction times, environmentally-friendly reaction media, easily isolation of the products, simple preparation, full characterization and recoverability of the nanocatalyst by an external magnet and reusing several times without significant loss of activity. |
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Keywords: | Ultrasonic irradiation Core shell nanocatalyst Magnetic nanoparticles Green chemistry Tetrazolopyrimidine KLYPXVWAKFQJOO-UHFFFAOYSA-N LGBNVJICWYECGE-UHFFFAOYSA-N KTILRPDVMMNLQP-UHFFFAOYSA-N ZHMOMHUTTHUUCX-UHFFFAOYSA-N MEWLJUIFFQCPTH-UHFFFAOYSA-N YTSBCUUIINEESH-UHFFFAOYSA-N MBKRQLPNDTWUHT-UHFFFAOYSA-N BYNMBKNIGYBWCZ-UHFFFAOYSA-N SLDHHOKXQQYWEC-UHFFFAOYSA-N SPCNFKLRAJDUKC-UHFFFAOYSA-N GRCXQQLGCXNWOB-UHFFFAOYSA-N CJOIDQNAGLWJIR-UHFFFAOYSA-N SNYKFSWOVGKZTL-UHFFFAOYSA-N YSEKBNQBMMOSTO-UHFFFAOYSA-N MXNZAGCNJDBAQG-UHFFFAOYSA-N ULRPISSMEBPJLN-UHFFFAOYSA-N |
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