title: Facile zinc(II)-mediated generation of 5-amino substituted 2,3-dihydro-1,2,4-oxadiazoles and their further ZnII-catalyzed and O2-involving transformations, New J. Chem., 39 (2015) 9330–9344, DOI: 10.1039/C5NJ02061A
metadata.name: dc.contributor.author
metadata.value: Smirnov, Andrey S.
metadata.lang: -
metadata.name: dc.contributor.author
metadata.value: Butukhanova, Ekaterina S.
metadata.lang: -
metadata.name: dc.contributor.author
metadata.value: Bokach, Nadezhda A.
metadata.lang: -
metadata.name: dc.contributor.author
metadata.value: Starova, Galina L.
metadata.lang: -
metadata.name: dc.contributor.author
metadata.value: Gurzhiy, Vladislav V.
metadata.lang: -
metadata.name: dc.contributor.author
metadata.value: Kukushkin, Vadim Yu.
metadata.lang: -
metadata.name: dc.date.accessioned
metadata.value: 2016-04-15T17:15:44Z
metadata.lang: -
metadata.name: dc.date.available
metadata.value: 2016-04-15T17:15:44Z
metadata.lang: -
metadata.name: dc.date.issued
metadata.value: 2015
metadata.lang: -
metadata.name: dc.identifier.issn
metadata.value: 1144-0546
metadata.lang: -
metadata.name: dc.identifier.uri
metadata.value: http://hdl.handle.net/11701/2107
metadata.lang: -
metadata.name: dc.description.abstract
metadata.value: ZnII-activated cyanamides NCNR2 (R2 = Me2, Et2, C5H10, C4H8O, Ph2) react with the acyclic N-alkyl ketonitrones Ph2C=N+(O–)R’ (R’ = Me, CH2Ph) and N-aryl ketonitrones (R’ = Ph, p-BrC6H4, p-EtC6H4) under mild conditions. Uncomplexed 5-aminosubstituted 2,3-dihydro-1,2,4-oxadiazoles (6 examples; 49–82%) were obtained in zinc(II)-involving cycloaddition of the N-alkyl ketonitrones to the cyanamide substrates; these 2,3-dihydro-1,2,4-oxadiazoles undergo ring-opening giving carbamoylamidines and methylidenureas. The N-aryl ketonitrones react with ZnII-activated cyanamides giving the open-chain systems, viz. carbamoylamidines, N'-(2-(diphenylmethylidene)amino)-phenyl-N,N-carbamimidic acids, and methylidenureas, which are presumably formed via the cycloaddition route followed by the N–O cleavage induced by the acceptor character of the aryl groups.
metadata.lang: en_GB
metadata.name: dc.language.iso
metadata.value: en
metadata.lang: en_GB
metadata.name: dc.publisher
metadata.value: RSC
metadata.lang: en_GB
metadata.name: dc.relation.ispartofseries
metadata.value: New Journal of Chemistry;39
metadata.lang: -
metadata.name: dc.subject
metadata.value: 2,3-Dihydro-1,2,4-oxadiazoles
metadata.lang: en_GB
metadata.name: dc.title
metadata.value: Facile zinc(II)-mediated generation of 5-amino substituted 2,3-dihydro-1,2,4-oxadiazoles and their further ZnII-catalyzed and O2-involving transformations, New J. Chem., 39 (2015) 9330–9344, DOI: 10.1039/C5NJ02061A
metadata.lang: en_GB
metadata.name: dc.type
metadata.value: Article
metadata.lang: en_GB
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resources.url: https://dspace.spbu.ru/bitstream/11701/2107/1/zinc-4000x3000-6.jpg
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resources.size: 1,48 MB