Retro Diels Alder protocol for regioselective synthesis of novel [1,2,4]triazolo[4,3-a]pyrimidin-7(1H)-ones

Said, Awad I.; Palkó, Márta; Haukka, Matti; Fülöp, Ferenc

doi:10.1039/D0RA04345A

dc.contributor.author	Said, Awad I.
dc.contributor.author	Palkó, Márta
dc.contributor.author	Haukka, Matti
dc.contributor.author	Fülöp, Ferenc
dc.date.accessioned	2020-10-16T04:47:52Z
dc.date.available	2020-10-16T04:47:52Z
dc.date.issued	2020
dc.identifier.citation	Said, 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.other	CONVID_42617176
dc.identifier.uri	https://jyx.jyu.fi/handle/123456789/72200
dc.description.abstract	Reactions 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.mimetype	application/pdf
dc.language	eng
dc.language.iso	eng
dc.publisher	Royal Society of Chemistry
dc.relation.ispartofseries	RSC Advances
dc.rights	CC BY-NC 4.0
dc.title	Retro Diels Alder protocol for regioselective synthesis of novel [1,2,4]triazolo[4,3-a]pyrimidin-7(1H)-ones
dc.type	article
dc.identifier.urn	URN:NBN:fi:jyu-202010166252
dc.contributor.laitos	Kemian laitos	fi
dc.contributor.laitos	Department of Chemistry	en
dc.contributor.oppiaine	Epäorgaaninen kemia	fi
dc.contributor.oppiaine	Epäorgaaninen ja analyyttinen kemia	fi
dc.contributor.oppiaine	Inorganic Chemistry	en
dc.contributor.oppiaine	Inorganic and Analytical Chemistry	en
dc.type.uri	http://purl.org/eprint/type/JournalArticle
dc.type.coar	http://purl.org/coar/resource_type/c_2df8fbb1
dc.description.reviewstatus	peerReviewed
dc.format.pagerange	33937-33943
dc.relation.issn	2046-2069
dc.relation.numberinseries	56
dc.relation.volume	10
dc.type.version	publishedVersion
dc.rights.copyright	© The Royal Society of Chemistry 2020
dc.rights.accesslevel	openAccess	fi
dc.subject.yso	typpiyhdisteet
dc.subject.yso	kemiallinen synteesi
dc.subject.yso	aromaattiset yhdisteet
dc.format.content	fulltext
jyx.subject.uri	http://www.yso.fi/onto/yso/p640
jyx.subject.uri	http://www.yso.fi/onto/yso/p8468
jyx.subject.uri	http://www.yso.fi/onto/yso/p23502
dc.rights.url	https://creativecommons.org/licenses/by-nc/4.0/
dc.relation.doi	10.1039/D0RA04345A
jyx.fundinginformation	We 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).
dc.type.okm	A1

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Retro Diels Alder protocol for regioselective synthesis of novel [1,2,4]triazolo[4,3-a]pyrimidin-7(1H)-ones

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