Browsing by Subject "-ylide"

Now showing 1 - 1 of 1
  • Thumbnail Image
    Item
    Open Access
    Indolizines and pyrrolo[1,2- c ]pyrimidines decorated with a pyrimidine and a pyridine unit respectively
    (2015) Popa, Marcel Mirel; Georgescu, Emilian; Caira, Mino R; Georgescu, Florentina; Draghici, Constantin; Stan, Raluca; Deleanu, Calin; Dumitrascu, Florea
    The three possible structural isomers of 4-(pyridyl)pyrimidine were employed for the synthesis of new pyrrolo[1,2-c]pyrimidines and new indolizines, by 1,3-dipolar cycloaddition reaction of their corresponding N-ylides generated in situ from their corresponding cycloimmonium bromides. In the case of 4-(3-pyridyl)pyrimidine and 4-(4-pyridyl)pyrimidine the quaternization reactions occur as expected at the pyridine nitrogen atom leading to pyridinium bromides and consequently to new indolizines via the corresponding pyridinium N-ylides. However, in the case of 4-(2-pyridyl)pyrimidine the steric hindrance directs the reaction to the pyrimidinium N-ylides and, subsequently, to the formation of the pyrrolo[1,2-c]pyrimidines. The new pyrrolo[1,2-c]pyrimidines and the new indolizines were structurally characterized through NMR spectroscopy. The X-ray structures of two of the starting materials, 4-(2-pyridyl)pyrimidine and 4-(4-pyridyl)pyrimidine, are also reported.