Lithiation of N-(2-alkylphenyl) alkanamides and related compounds. A modified Madelung indole synthesis

WJ Houlihan, VA Parrino, Y Uike

文献索引：Houlihan, William J.; Parrino, Vincent A.; Uike, Yasuyuki Journal of Organic Chemistry, 1981 , vol. 46, # 22 p. 4511 - 4515

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被引用次数: 104

摘要

A modified Madelung synthesis for the conversion of N (alkylpheny1) 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 “C. Several examples where products other than indoles were formed from the starting amide are also reported.