N–H Insertion reactions of rhodium carbenoids. Part 3. 1 The development of a modified Bischler indole synthesis and a new protecting-group strategy for indoles

…, CJ Moody, S Muthusamy, E Swann

Index: Bashford, Katherine E.; Cooper, Anthony L.; Kane, Peter D.; Moody, Christopher J.; Muthusamy, Sendogagounder; Swanna, Elizabeth Journal of the Chemical Society. Perkin Transactions 1, 2002 , # 14 p. 1672 - 1687

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Citation Number: 57

Abstract

A modified version of the Bischler indole synthesis has been developed in which the key step is the N–H insertion reaction of rhodium carbene intermediates derived from α-diazo-β- ketoesters with anilines. Thus N-methylanilines 1 react with diazoketoesters 2 in the presence of dirhodium (II) acetate to give (N-arylamino) ketones 3, cyclisation of which using boron trifluoride–ethyl acetate or acidic ion exchange resin gives the indoles 4. In order to ...