135679-01-5Relevant articles and documents
Heterocyclic Transformations. Part 3. Thiolate Ion-induced Transformations of 6-Methyl-1,3-oxazine-2,4(3H)-diones to 3-(Alkyl/arylthio)but-2-enamides
Kumar, Subodh,Chimni, Swapandeep Singh,Singh, Harjit
, p. 1391 - 1395 (2007/10/02)
Thiolate ions generated under phase-transfer catalytic conditions react exclusively at C-6 of 3-alkyl-6-methyl-1,3-oxazine-2,4(3H)-diones to give (E)- and (Z)-3-(alkylthio)but-2-enamides.With binucleophiles having at least one thiol group, the E+Z thiobutenamides are initially formed and their further transformation depends on the nature on the second nucleophile.The bulk of the N-3 substituent of the oxazine and the thiol exercise steric control on the rate and mode of the reaction.