Direct diastereoselective introduction of l-menthol residue into 1,2,4-triazin-5(4H)-one |
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| Authors: | Zyryanov G V Rusinov V L Chupakhin O N Krasnov V P Levit G L Kodess M I Shtukina T S |
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| Institution: | (1) Urals State Technical University, 19 ul. Mira, 620002 Ekaterinburg, Russian Federation, Russia;(2) I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 20 ul. S. Kovalevskoi, 620219 Ekaterinburg, Russian Federation, Russia |
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| Abstract: | The reaction of 3-phenyl-1,2,4-triazin-5(4H)-one (1) with l-menthol in the presence of aliphatic acid anhydrides results in (6S)- and (6R)-1-acyl-6-(l-menth-3-yl)-1,6-dyhydro-3-phenyl-1,2,4-triazin-5(4H)-ones. The reaction is diastereoselective with predominant formation of (6S)-isomers. The reaction diastereoselectivity increases with enhancement of the steric hindrance in the vicinity of the reaction center of the azine. |
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| Keywords: | 3-phenyl-1 2 4-triazin-5(4H)-one l-menthol diastereoselectivity acetic anhydride isobutyric anhydride 1-acyl-6-(l-menth-3-yloxy)-3-phenyl-1 6-dyhydro-1 2 4-triazin-5(4H)-ones nucleophilic addition |
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