Preparation of Perfluoroalkylated Benzoheterocyclic Compounds Using Hexafluoro-1,2-epoxypropane

Abstract

Abstract Utilizing the high reactivity of hexafluoro-1,2-epoxypropane (HFPO, hexafluoropropylene oxide), several new benzoheterocyclic compounds containing CF3 and C2F5 were prepared as follows: (1) 2-(pentafluoroethyl)benzoxazoles by treating 2-aminophenols with HFPO/Et3N, followed by dehydrating cyclization, (2) 3-(trifluoromethyl)2H-1,4-benzoxazin-2-ones, 3-(trifluoromethyl)-2(1H)-quinoxalinone and 2-fluoro-2-(trifluoromethyl)-2,3-dihydro-1,4-benzothiazin-3-one by reactions of ortho-bifunctional benzenes with HFPO, and (3) 2-(pentafluoroethyl)-4H-3,1-benzoxazin-4-one by treating anthranilic acid with HFPO/Et3N.