A1 Journal article (refereed)
Retro Diels Alder protocol for regioselective synthesis of novel [1,2,4]triazolo[4,3-a]pyrimidin-7(1H)-ones (2020)


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. RSC Advances, 10(56), 33937-33943. https://doi.org/10.1039/D0RA04345A


JYU authors or editors


Publication details

All authors or editorsSaid, Awad I.; Palkó, Márta; Haukka, Matti; Fülöp, Ferenc

Journal or seriesRSC Advances

eISSN2046-2069

Publication year2020

Volume10

Issue number56

Pages range33937-33943

PublisherRoyal Society of Chemistry

Publication countryUnited Kingdom

Publication languageEnglish

DOIhttps://doi.org/10.1039/D0RA04345A

Publication open accessOpenly available

Publication channel open accessOpen Access channel

Publication is parallel published (JYX)https://jyx.jyu.fi/handle/123456789/72200


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.


Keywordsaromatic compoundsnitrogen compoundschemical synthesis


Contributing organizations


Ministry reportingYes

Reporting Year2020

JUFO rating1


Last updated on 2024-22-04 at 13:10