Aminolysis of pyrido[2,1-i]purines

Abstract

7-Oxo-3-(tetrahydropyran-2-yl)-7H-pyrido[2,1-i]purines (1) are highly fluorescent molecules with absorption and emission in the visible region. Under mild conditions these compounds react with primary and secondary amines and the products (2) formed are non-fluorescent. Kinetic studies reveal a mechanism, which resembles ester aminolysis and is completely second order in monoamine concentration. Diazabicyclo-octane accelerates the reaction as does 2-pyridone. In addition kinetics of reactions with diamines are described.