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 |
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| Authors: | Awad I Said Mrta Palk Matti Haukka Ferenc Fülp |
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| Institution: | 1.Institute of Pharmaceutical Chemistry, University of Szeged, Eötvös u. 6, H-6720 Szeged, Hungary; (A.I.S.); (F.F.);2.Chemistry Department, Faculty of Science, Assiut University, Assiut 71516, Egypt;3.Interdisciplinary Excellence Center, Institute of Pharmaceutical Chemistry, University of Szeged, H-6720 Szeged, Hungary;4.Department of Chemistry, University of Jyväskulä, FIN-40014 Jyväskulä, Finland; |
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| Abstract: | The regioselective synthesis of cis and trans stereoisomers of variously functionalized octahydro1,2,4]triazolo4,3-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]triazolo4,3-a]quinazolin-5-ones rather than the linear isomers 1,2,4]triazolo4,3-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. |
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| Keywords: | regioselective reactions hydrazonoyl chlorides 2-thioxopyrimidin-4-ones [1 2 4]triazolo[4 3-a]quinazolin-5-ones |
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