1242594-80-4Relevant academic research and scientific papers
Diastereoselective synthesis of 1-alkyl-2,4,6-trioxoperhydropyrimidine-5- spiro-3′-(1′,2′,3′,4′-tetrahydroquinolines)
Krasnov, Konstantin A.,Kartsev, Victor G.,Khrustalev, Victor N.
, p. 6054 - 6061 (2010)
Knoevenagel products formed by the condensation of N-monoalkyl barbituric acids with o-tert-amino benzaldehydes undergo tert-amino effect reactions (T-reactions) yielding 1-alkyl-2,4,6-trioxoperhydropyrimidine-5-spiro-3′- (1′,2′,3′,4′-tetrahydroquinoline) derivatives as a mixture of (S*,S*)- and (S*,R*)-diastereomers. Mostly, the major diastereomer has the S*,S*-configuration. According to X-ray diffraction data in the solid form and NOE data in solution, diastereoselectivity of the T-reactions can be associated with the structure of the Knoevenagel products whose conformation is fixed by the strong intramolecular C-H?π interaction.
