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

Journal or series: RSC Advances

eISSN: 2046-2069

Publication year: 2020

Volume: 10

Issue number: 56

Pages range: 33937-33943

Publisher: Royal Society of Chemistry

Publication country: United Kingdom

Publication language: English

DOI: https://doi.org/10.1039/D0RA04345A

Publication open access: Openly available

Publication channel open access: Open Access channel

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


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.

Keywords: aromatic compounds; nitrogen compounds; chemical synthesis

Contributing organizations

Ministry reporting: Yes

Reporting Year: 2020

JUFO rating: 1

Last updated on 2021-07-07 at 21:36