One-Pot Syntheses of 2-N-Alkylamino-, 2-N-Phenylamino-, 2-N, N-Dialkylamino-, and 2-N-Alkyl-N-phenylaminothiophenes

Abstract

A number of 2-N-alkylamino- or 2-N-phenylamino-, 2-N, N-dialkylamino-, and 2-N-alkyl-N-phenylaminothiophenes have been prepared in good yields by adding a solution of tert-butylalcohol and potassium tert-butoxide in dimethylsulfoxide to a solution of the adduct from a lithiated 1-alkyne, RCH2C≡CLi, or the lithiated allene, tBuCH=C=CHLi, and isothiocyanate, R′N=C=S, in tetrahydrofuran and subsequently hydrolyzing the reaction mixture or quenching it with methyl iodide.