On the synthesis and reactivity of 4-(oxiran-2-ylmethoxy)cinnoline: Targeting a cinnoline analogue of propranolol

Abstract

The title compound (2) was prepared by reaction of 4-chlorocinnoline with glycidol/sodium hydride in dry DMF, since treatment of cinnolin-4-ol with epichlorohydrin as well as oxidation of 4-allyloxycinnoline did not succeed. Reaction of 2 with primary and secondary amines leads to aminoalcohols characterized by a high tendency to rearrangement and/or elimination. The obtained products were subjected to detailed multinuclear ( 1H, 13C, 15N) NMR studies. © Österreichische Apotheker-Verlagsgesellschaft m. b. H.