SYNTHESIS OF 3-SUBSTITUTED DIHYDRO-1-1PHENYLAMINO-1H-PYRROLO[1,2-A]IMIDAZOLE-2,5(3H,6H)-DIONES FROM A-AMINO ACID PHENYLHYDRAZIDES AND LEVULINIC ACID

Abstract

α-N-Protected amino acid hydrazides (1) readily reacted with NaBH4 to afford 5-substituted 4,5-dihydro-1,2,4-triazin- 3(2H)-one derivatives 2 in good yields. Unfortunately, the reaction caused partial racemization at the α-amino acidic carbon atom of the starting hydrazide. A mechanism, supported by experimental evidence, has been proposed in an attempt to explain this to date unprecedented reaction. The structure of compounds 2 was confirmed by X-ray structural analysis.