180056-61-5Relevant articles and documents
Novel efficient synthesis of 3,4-dihydro-6-substituted-3-phenylpyrimidin- 2(1H)-ones
Frija, Luís M. T.,Khmelinskii, Igor V.,Cristiano, M. Lurdes S.
, p. 6757 - 6760 (2005)
A new attractive and convenient strategy for the synthesis of 3,4-dihydro-6-substituted-3-phenylpyrimidin-2(1H)-ones is described. Photolysis (λ = 254 nm) of 4-allyl-tetrazolones in alcoholic solutions produces the corresponding pyrimidinones as the sole product in nearly quantitative yields, with simultaneous extrusion of molecular nitrogen. Work-up procedures consist in the simple evaporation of the solvent under reduced pressure, in mild conditions. Heats of reaction for the photocleavage process of 4-allyltetrazolones were calculated, indicating high stability of the resulting products.
A kinetic investigation of the thermal rearrangement of allyloxytetrazoles to N-allyltetrazolones
Cristiano, M. Lurdes S.,Johnstone, Robert A. W.
, p. 489 - 494 (2007/10/03)
The mechanism of the thermal rearrangement of 1-aryl-5-allyloxytetrazoles 1 to give 1-aryl-4-allyltetrazolones 2 in very high yield has been investigated through kinetic studies in one polar and one less polar solvent. The results suggest mainly a concerted [3,3] sigmatropic process, in which a partially positively charged allyl group migrates from oxygen to nitrogen, similar to the polar transition state found in the Claisen rearrangement.
