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

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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

Julkaistu sarjassa

RSC Advances

Tekijät

Said, Awad I. |

Palkó, Márta |

Haukka, Matti |

Fülöp, Ferenc

Päivämäärä

2020

Oppiaine

Epäorgaaninen kemia Epäorgaaninen ja analyyttinen kemia Inorganic Chemistry Inorganic and Analytical Chemistry

Tekijänoikeudet

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.

Julkaisija

Royal Society of Chemistry

ISSN Hae Julkaisufoorumista

2046-2069

Lisätietoja rahoituksesta

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).

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