413608-64-7Relevant academic research and scientific papers
A new protecting-group strategy for indoles
Bashford, Katherine E,Cooper, Anthony L,Kane, Peter D,Moody, Christopher J
, p. 135 - 137 (2007/10/03)
The 2-phenylsulfonylethyl group is a useful alkyl protecting group for nitrogen during indole synthesis; it is readily removed from the indole nitrogen under basic conditions.
N-H insertion reactions of rhodium carbenoids. Part 3. The development of a modified Bischler indole synthesis and a new protecting-group strategy for indoles
Bashford, Katherine E.,Cooper, Anthony L.,Kane, Peter D.,Moody, Christopher J.,Muthusamy, Sendogagounder,Swanna, Elizabeth
, p. 1672 - 1687 (2007/10/03)
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 extend this method to the synthesis of N-unsubstituted indoles, a new protecting group strategy for indoles was developed. In this, anilines are reacted with α,β-unsaturated-esters or -sulfones to give the conjugate addition products 6 and 9, cyclisation of which gives indoles 8 and 11. The N-(2-ethoxycarbonylethyl)- and -(2-sulfonylethyl)- protecting groups are readily removed from indoles 8 and 11 by treatment with base.
