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dc.contributor.authorSaid, Awad I.
dc.contributor.authorPalkó, Márta
dc.contributor.authorHaukka, Matti
dc.contributor.authorFülöp, Ferenc
dc.date.accessioned2020-10-16T04:47:52Z
dc.date.available2020-10-16T04:47:52Z
dc.date.issued2020
dc.identifier.citationSaid, A. I., Palkó, M., Haukka, M., & Fülöp, F. (2020). Retro Diels Alder protocol for regioselective synthesis of novel [1,2,4]triazolo[4,3-a]pyrimidin-7(1H)-ones. <i>RSC Advances</i>, <i>10</i>(56), 33937-33943. <a href="https://doi.org/10.1039/D0RA04345A" target="_blank">https://doi.org/10.1039/D0RA04345A</a>
dc.identifier.otherCONVID_42617176
dc.identifier.urihttps://jyx.jyu.fi/handle/123456789/72200
dc.description.abstractReactions of diastereochemically varied norbornene-condensed 2-thioxopyrimidin-4-ones6and10with variously functionalized hydrazonoyl chlorides2a-hgave regioselectively angular norbornene-based [1,2,4]triazolo[4,3-a]pyrimidin-7(1H)-ones7a-hand11a,c-e, respectively. Thermal retro Diels-Alder (RDA) reaction of7a-hand11a,c-eresulted in the target compounds4a-has single products. On the other hand, reactions of thiouracil1and hydrozonoyl chlorides2a-egave regioselectively [1,2,4]triazolo[4,3-a]pyrimidinone-5(1H)-ones3a-e. The opposite regioselectivity of thiouracil1and norbornene-condensed 2-thioxopyrimidin-4-ones6and10was attributed to electronic factors according to DFT calculations. The angular structure of norbornene based [1,2,4]triazolo[4,3-a]pyrimidin-7(1H)-ones was confirmed by single crystal X-ray crystallography.en
dc.format.mimetypeapplication/pdf
dc.languageeng
dc.language.isoeng
dc.publisherRoyal Society of Chemistry
dc.relation.ispartofseriesRSC Advances
dc.rightsCC BY-NC 4.0
dc.titleRetro Diels Alder protocol for regioselective synthesis of novel [1,2,4]triazolo[4,3-a]pyrimidin-7(1H)-ones
dc.typearticle
dc.identifier.urnURN:NBN:fi:jyu-202010166252
dc.contributor.laitosKemian laitosfi
dc.contributor.laitosDepartment of Chemistryen
dc.contributor.oppiaineEpäorgaaninen kemiafi
dc.contributor.oppiaineEpäorgaaninen ja analyyttinen kemiafi
dc.contributor.oppiaineInorganic Chemistryen
dc.contributor.oppiaineInorganic and Analytical Chemistryen
dc.type.urihttp://purl.org/eprint/type/JournalArticle
dc.description.reviewstatuspeerReviewed
dc.format.pagerange33937-33943
dc.relation.issn2046-2069
dc.relation.numberinseries56
dc.relation.volume10
dc.type.versionpublishedVersion
dc.rights.copyright© The Royal Society of Chemistry 2020
dc.rights.accesslevelopenAccessfi
dc.subject.ysotyppiyhdisteet
dc.subject.ysokemiallinen synteesi
dc.subject.ysoaromaattiset yhdisteet
dc.format.contentfulltext
jyx.subject.urihttp://www.yso.fi/onto/yso/p640
jyx.subject.urihttp://www.yso.fi/onto/yso/p8468
jyx.subject.urihttp://www.yso.fi/onto/yso/p23502
dc.rights.urlhttps://creativecommons.org/licenses/by-nc/4.0/
dc.relation.doi10.1039/D0RA04345A
jyx.fundinginformationWe are grateful to the Hungarian Research Foundation (OTKA No. K 115731). The financial support of the GINOP-2.3.2-15-2016-00038 project is acknowledged. Ministry of Human Capacities, Hungary grant 20391-3/2018/FEKUSTRAT is acknowledged. In addition, Tempus Public Foundation is also acknowledged for its financial support (No. AK-00167-002/2019).


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