Synthesis of functionalized pyrazin-2(1h)-ones via tele-nucleophilic substitution of hydrogen involving grignard reactants and electrophiles

The reaction of 6-chloro-1-methylpyrazin-2(1H)-one with Grignard reactants followed by quenching with different electrophiles gave access to a variety of 3,6-difunctionalized 1-methylpyrazin-2(1H)-ones. This regioselective three-component reaction represents the first example of a tele-nucleophilic substitution of hydrogen (SNH) in which the anionic σH adduct is quenched by electrophiles (other than a proton) before elimination takes place. Quenching the reaction with iodine (I2) or bromine (Br2) provides an alternative reaction pathway, yielding a 3-functionalized 6-chloro-1-methylpyrazin-2(1H)-one or 5-bromo-6-chloro-1-methylpyrazin-2(1H)-one, respectively. The halogens present offer opportunities for further selective transformations.

Publication year:2019

Keywords:A1 Journal article

BOF-keylabel:yes

BOF-publication weight:10

CSS-citation score:1

Authors:International

Authors from:Higher Education

Accessibility:Open