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, Awad I.; Palkó, Márta; Haukka, Matti; Fülöp, Ferenc (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. DOI: 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: http://doi.org/10.1039/D0RA04345A

Open Access: Publication published in an open 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.


Keywords: aromatic compounds; nitrogen compounds; chemical synthesis


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Preliminary JUFO rating: 1


Last updated on 2020-16-10 at 07:47