A1 Journal article (refereed)
Angular Regioselectivity in the Reactions of 2-Thioxopyrimidin-4-ones and Hydrazonoyl Chlorides : Synthesis of Novel Stereoisomeric Octahydro[1,2,4]triazolo[4,3-a]quinazolin-5-ones (2020)


Said, Awad I.; Palkó, Márta; Haukka, Matti; Fülöp, Ferenc (2020). Angular Regioselectivity in the Reactions of 2-Thioxopyrimidin-4-ones and Hydrazonoyl Chlorides : Synthesis of Novel Stereoisomeric Octahydro[1,2,4]triazolo[4,3-a]quinazolin-5-ones. Molecules, 25 (23), 5673. DOI: 10.3390/molecules25235673


JYU authors or editors


Publication details

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

Journal or series: Molecules

eISSN: 1420-3049

Publication year: 2020

Volume: 25

Issue number: 23

Article number: 5673

Publisher: MDPI

Publication country: Switzerland

Publication language: English

DOI: https://doi.org/10.3390/molecules25235673

Open Access: Publication published in an open access channel

Publication is parallel published (JYX): https://jyx.jyu.fi/handle/123456789/73402


Abstract

The regioselective synthesis of cis and trans stereoisomers of variously functionalized octahydro[1,2,4]triazolo[4,3-a]quinazolin-5-ones was performed. The 2-thioxopyrimidin-4-ones used in the synthesis reacted with hydrazonoyl chlorides in a regioselective manner to produce the angular regioisomers [1,2,4]triazolo[4,3-a]quinazolin-5-ones rather than the linear isomers [1,2,4]triazolo[4,3-a]quinazolin-5-ones. The synthesis process took place with electronic control. The angular regiochemistry of the products was confirmed by X-ray experiments and two-dimensional NMR studies.


Keywords: organic compounds; nitrogen compounds; chemical synthesis; isomerism

Free keywords: regioselective reactions; hydrazonoyl chlorides; 2-thioxopyrimidin-4-ones; [1,2,4]triazolo[4,3-a]quinazolin-5-ones


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Ministry reporting: Yes

Preliminary JUFO rating: 1


Last updated on 2020-23-12 at 10:30