Novel Synthesis of 8-Deaza-5,6,7,8-tetrahydroaminopterin Analogues via an Aziridine Intermediate

Abstract

An efficient method for the construction of the tetrahydrofolate skeleton is described. Starting from pterin analogues and aromatic amines, 8-deaza-5,6,7,8-tetrahydroaminopterin derivatives and the heterocyclic benzoyl isosteres were synthesized via a novel aziridine intermediate. Following this method, the byproducts of carbon-nitrogen bond hydrogenolysis in traditional synthetic strategy can be completely avoided.

Keywords

• tetrahydrofolate
• aziridine
• catalytic hydrogenation
• solvent-free