Affiliation:
1. Institute of Organic Chemistry I, Ulm University , Albert-Einstein-Allee 11, D-89081 Ulm , Germany
Abstract
Abstract
4-CF3-pyrido[1,2-a]pyrimidin-5-ium triflates could be prepared in fair to high yields from acetylenic iminium salts R-C≡C–C(CF3)=N+Me2·CF3SO3
− and 2-aminopyridinium triflate under thermal conditions. Their reactions with protic heteronucleophiles, leading to 4-CF3, 4-XR-substituted 1,4-dihydropyrido[1,2-a]pyrimidin-5-ium salts, have been studied and reversible addition as well as subsequent opening of the pyrimidine ring have been observed. The cyclocondensation of a 3-phenyl-propyniminium triflate and 3-aminoyridinium triflate required strong thermal activation and yielded a 4-CF3-and a 4-CF3,5-CH3-[1,7]naphthyridine. A 1-CF3-benzo[f][1,7]naphthyridine was obtained from the same propyniminium salt and 3-aminoquinolinium triflate.
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