Journals / Turkish Journal of Chemistry / 2010 / Cilt: 34 - Sayı: 6

Ethyl 5-oxo-3-arylamino-2,5-dihydroisoxazole-4- carboxylates as sources of imidazopyrimidine and aminoindole derivatives

Pages
847–858
DOI
—

Abstract

The reaction of ethyl 5-oxo-3-arylamino-2,5-dihydroisoxazole-4- carboxylates with 2-chloropyrimidine and 2-chlorobenzoxazole gave the corresponding isoxazolones with pyrimidine and benzoxazole rings substituted on N-2. Their rearrangements with triethylamine in ethanol produced the corresponding imidazopyrimidine and aminoindole derivatives, respectively, through intramolecular cyclisation.

Özet

The reaction of ethyl 5-oxo-3-arylamino-2,5-dihydroisoxazole-4- carboxylates with 2-chloropyrimidine and 2-chlorobenzoxazole gave the corresponding isoxazolones with pyrimidine and benzoxazole rings substituted on N-2. Their rearrangements with triethylamine in ethanol produced the corresponding imidazopyrimidine and aminoindole derivatives, respectively, through intramolecular cyclisation.

Keywords: Isoxazolones, 2-chloropyrimidine, 2-chlorobenzoxazole, rearrangements, imidazopyrimidines, aminoindoles