Journal of Organic Chemistry p. 4511 - 4515 (1981)
Update date:2022-08-05
Topics:
Houlihan, William J.
Parrino, Vincent A.
Uike, Yasuyuki
A modified Madelung synthesis for the conversion of N-(alkylphenyl)alkanamides and related compounds to indoles, benzindoles, and azindoles has been developed.This procedure consists of treating the amide with 2 or 3 equiv of n-butyllithium or lithium diisopropylamide in tetrahydrofuran at temperatures from -20 to +25 deg C.Several examples where products other than indoles were formed from the starting amide are also reported.
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