Photoinduced cyclizations of mono-and dianions of N-acyl-o-chloroanilines and N-acyl-o-chlorobenzylamines as general methods for the synthesis of oxindoles and 1 …

RR Goehring, YP Sachdeva, JS Pisipati…

Index: Goehring, R. Richard; Sachdeva, Yesh P.; Pisipati, Jyothi S.; Sleevi, Mark C.; Wolfe, James F. Journal of the American Chemical Society, 1985 , vol. 107, # 2 p. 435 - 443

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Citation Number: 127

Abstract

Abstract: Formation of the monoanions of a series of N-acyl-N-alkyl-o-chloroanilines by means of LDA in THF followed by irradiation with near-UV light affords 1, 3-dialkyloxindoles in good yields. Similar photoinduced cyclizations of dianions derived from N-acyl-o- chloroanilines leads to 3-alkyloxindoles. Photocyclizations of mono-and dianions prepared from a,@-unsaturated o-haloanilides proceed to form 3-alkylideneoxindoles. Carbanions ...