Effect of Bronsted Acids and Bases, and Lewis Acid (Sn2+) on the Regiochemistry of the Reaction of Amines with Trifluoromethyl-β-diketones: Reaction of 3- …

M De Rosa, D Arnold, D Hartline, L Truong…

Index: De Rosa, Michael; Arnold, David; Hartline, Douglas Journal of Organic Chemistry, 2013 , vol. 78, # 17 p. 8614 - 8623

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Abstract

Reaction of 3-aminopyrrole (as its salt) with trifluoromethyl-β-diketones gave γ-1 H-pyrrolo [3, 2-b] pyridines via reaction at the less reactive carbonyl group. The trifluoromethyl group increased the electrophilicity of the adjacent carbonyl group and decreased the basicity of the hydroxyl group of the CF3 amino alcohol formed. This amino alcohol was formed faster, but its subsequent dehydration to the β-enaminone was slow resulting in the preferential ...