Synlett

NH Insertion reactions of rhodium carbenoids: a modified Bischler indole synthesis

CJ Moody, E Swann

Index: Moody, Christopher J.; Swann, Elizabeth Synlett, 1998 , # 2 p. 135 - 136

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Citation Number: 26

Abstract

The Bischler indole synthesis, discovered over 100 years ago,1 involves the reaction of anilines with α-halo-ketones or -acetals and the subsequent acid catalysed cyclisation of the resulting α-(N-arylamino)- ketones or -acetals (the Nordlander modification).2,3 We now report a modification in which the key step is the NH insertion reaction4 of anilines with rhodium carbenoids generated from diazocarbonyl compounds to give α-(N-arylamino)ketones for subsequent cyclisation.5

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