Journal of Organic Chemistry p. 778 - 782 (1981)
Update date:2022-08-04
Topics:
Nordlander, J. Eric
Catalane, David B.
Kotian, Kirtivan D.
Stevens, Randall M.
Haky, Jerome E.
N-(trifluoroacetyl)indoles (3) are produced in high yield from appropriately ring-substituted N-(trifluoroacetyl)-2-anilino acetals (2) in boiling trifluoroacetic acid containing excess trifluoroacetic anhydride.Mild saponification provides the free indoles nearly quantitatively.The scope of the reaction is discussed.The ring closure follows solvolytic substitution of a trifluoroacetoxy group for one of the ethoxy groups in 2.The method has been extended to cyclization of N-(trifluoroacetyl)-α-anilinoacetone in hot polyphosphoric acid followed by saponification to yield 3-methylindole.
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