An unprecedented oxidative coupling of alkanones with 3-(pyridin-2-yl)-4,5-dihydro-1,2,4-triazin-6(1H)-one coordinated to palladium(II)

Add time:08/26/2019    Source:sciencedirect.com

A synthesis of 3-(pyridin-2-yl)dihydro-1,2,4-triazinone (1) is achieved utilizing the appropriate “in situ generated” nitrile imine 1,3-dipole. In solution, compound 1 rapidly reacts with dichlorobis(benzonitrile)palladium(II) to form dichloro[3-(pyridin-2-yl)dihydro-1,2,4-triazinone]palladium(II) (2). Interestingly, compound 2 undergoes oxidative C–C coupling reaction with 2-propanone and 2-butanone at reflux to deliver the corresponding Pd-complexes chloro[1-(4-chlorophenyl)-5-(2-oxopropyl)-3-(pyridin-2-yl)-1,2,4-triazin-6(1H)-one]palladium(II) (3) and chloro[1-(4-chlorophenyl)-5-(2-oxobutyl)-3-(pyridin-2-yl)-1,2,4-triazin-6(1H)-one]-palladium(II) (4) that incorporate masked dehydro-4-oxo-norvaline and dehydro-4-oxo-norleucine, respectively. Structures of the latter complexes were evidenced from spectral data and confirmed by single-crystal X-ray crystallography.

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