Strong potassium channel-activating effects were found among a series of novel 4- substituted 3, 4-dihydro-2H-1, 4-benzoxazine derivatives. The key step in preparation was the nucleophilic substitution of 3, 4-dihydro-2H-1, 4-benzoxazine (3) with activated halogenopyridines, such as halogenopyridine N-oxides (15a-c) and the borane adduct (15d) of 4-bromopyridine. Structure-activity relationship studies identified 2-(3, 4-dihydro-2 ...