Nucleophilic substitution by 3-amino-1,2-propanediol in nitropyrazines and nitroquinoxalines

Treatment of 2-chloro-3-nitropyrazine and 2-chloro-5-nitropyrazine with 3-amino-1, 2-propanediol affords products derived from displacement of chloride, while similar reaction of methyl 3-nitropyrazinoate and 2-chloro-3-nitroquinoxaline gives clean nitro group replacement. Analogous reaction of methyl 6-chloro-3-nitropyrazinoate affords a mixture containing products derived from competitive displacement of chloride and nitrite.