SYNTHESES OF POTENT MUTAGENS IN TRYPTOPHAN PYROLYSATES

Abstract

The mutagenic γ-carbolines, 3-amino-1-methyl-5H-pyrido[4,3-b]indole (IV) and 3-amino-1,4-dimethyl-5H-pyrido[4,3-b]indole (XIII) have been synthesized by condensation of 3-acetylindole-2-acetonitrile (III) with ammonia and by thermal decomposition of 2-amino-3,6-dimethyl-4-(1-benzotriazolyl)pyridine (XII), respectively. Synthesis of IV has been achieved by an alternative route involving acid catalyzed cyclization of α-acetamido-β-(2-indole)propionic acid (V), followed by dehydrogenation and Curtius rearrangement.