Silica Gel??Mediated Hydroamination/Semipinacol Rearrangement of 2??Alkylaminophenylprop??1??yn??3??ols: Synthesis of 2??Oxindoles from Alkynes and 1??(2?? …

D Susanti, LLR Ng, PWH Chan

Index: Susanti, Dewi; Ng, Linda Li Ru; Chan, Philip Wai Hong Advanced Synthesis and Catalysis, 2014 , vol. 356, # 2-3 p. 353 - 358

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Citation Number: 8

Abstract

Abstract: 2-Alkylaminophenylprop-1-yn-3-ols, prepared from the lithium diisopropylamide (LDA)-mediated 1, 2-addition of alkynes to 1-(2-aminophenyl) ketones, can be converted to 3, 3-disubstituted 2-oxindoles by using silica gel in n-hexane/ethyl acetate (20: 1 v/v) as the reaction medium. The utility of the approach as a potential scale-up strategy for the synthesis of 2-oxindoles was exemplified by the large-scale synthesis of one adduct in excellent ...