Journal of Organic Chemistry p. 4107 - 4111 (1984)
Update date:2022-08-02
Topics:
Nordlander, Eric J.
Payne, Mark J.
Njoroge, George F.
Balk, Michael A.
Laikos George D.
Vishwanath, Vasanth M.
Several N-(trifluoroacetyl)-α-amino acid chlorides have been reacted with benzene, anisole, and veratrole in the presence of AlCl3 or SnCl4 to produce the corresponding aromatic ketones in fair to high yields.The products are reductible under neutral or acidic conditions to the corresponding N-(trifluoroacetyl)-β-hydroxy-β-arylakylamines or N-(trifluoroacetyl)-β-arylalkylamines.The latter can be readily detrifluoroacetylated by mild basic hydrolysis and thence converted to the corresponding 3-substituted 1,2,3,4-tetrahydroisoquinolines by condensation with formaldehyde.
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