33282-15-4, Name is 5-(4-Hydroxyphenyl)isoxazole-3-carboxylic acid, belongs to isoxazole compound, is a common compound. Safety of 5-(4-Hydroxyphenyl)isoxazole-3-carboxylic acidIn an article, once mentioned the new application about 33282-15-4.
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
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 alpha-diazo-beta-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 alpha,beta-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.
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Reference：
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem