SYNTHESIS OF 1-TRIFLUOROMETHYL-β-CARBOLINE DERIVATIVES

Article abstract of DOI:10.1016/S0022-1139(00)82939-5

Benzene-ring substituted 1-trifluoromethyl-β-carbolines (IV) were synthesized in 23-27percent overall yield by selenium dioxide dehydrogenation of the corresponding 1-trifluoromethyl-1,2,3,4-tetrahydro-β-carbolines(II); the latter compounds were obtained in high yield by Mannich-type condensation of the respective tryptamines with trifluoroacetaldehyde.Partial dehydrogenation of II with potassium permanganate provided 1-trifluoromethyl-3,4-dihydro-β-carbolines (III).L-tryptophan gave, following condensation, esterification and dehydrogenation, 3-carboethoxy-1-trifluoromethyl-β-carboline (IVf) in 84.8percent overall yield.The halogenation and nitration of 1-trifluoromethyl-β-carboline (IVa) were also examined.