A Regioselective Approach to 5-Substituted-3-amino-1,2,4-triazines

• Published in: Organic letters Vol. 5; no. 13; pp. 2271 - 2274
• Main Authors: Limanto, John, Desmond, Richard A, Gauthier, Donald R, Devine, Paul N, Reamer, Robert A, Volante, R. P
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 26.06.2003; Amer Chemical Soc
• Subjects: Chemistry; Chemistry, Organic; Physical Sciences; Science & Technology; OXIDATION; POTASSIUM-AMIDE; AMINATION

Nucleophilic displacement of readily available α,α-dibromoketones with excess morpholine gave the corresponding ketoaminals, which upon condensation with aminoguanidine in MeOH in the presence of AcOH afforded 5-substituted-3-amino-1,2,4-triazines in >95% regioselectivity and 45−76% isolated yiel...