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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Zyryanov, G.V., Rusinov, V.L., Chupakhin, O.N. et al. Direct diastereoselective introduction of l-menthol residue into 1,2,4-triazin-5(4H)-one. Russian Chemical Bulletin 53, 1290–1294 (2004). https://doi.org/10.1023/B:RUCB.0000042288.91508.68
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DOI: https://doi.org/10.1023/B:RUCB.0000042288.91508.68