Reaction of 3-Amino-2H-azirines with 2-Amino-4,6-dinitrophenol (Picramic Acid): Synthesis of Quinazoline- and 1,3-Benzoxazole Derivatives

Abstract

The reaction of 3-(dimethylamino)-2H-azirines 1a-c and 2-amino-4,6-dinitrophenol (picramic acid, 2) in MeCN at 0° to room temperature leads to a mixture of the corresponding 1,2,3,4-tetrahydroquinazoline-2-one 5, 3-(dimethylamino)-1,2-dihydroquinazoline 6, 2-(1-aminoalkyl)-1,3-benzoxazole 7, and N-[2-(dimethylamino)phenyl]-alpha-aminocarboxamide 8 (Scheme 3). Under the same conditions, 3-(N-methyl-N-phenylamino)-2H-azirines 1d and 1e react with 2 to give exclusively the 1,3-benzoxazole derivative 7. The structure of the products has b Show more