Gassman oxindole synthesis

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The Gassman oxindole synthesis is a variant of the Gassman reaction that leads to substituted or unsubstituted oxindoles . It was first published in 1973 by Paul G. Gassman .

Oxindole synthesis according to Gassman

In a first stage, aniline or mono- N - alkylated anilines are reacted with tert-butyl hypochlorite to give the corresponding N -chloroaniline , which in turn is reacted with a β-methylthioester. Addition of a base, for example triethylamine , leads to a sigmatropic rearrangement and the intermediate product formed can be cyclized to the desired oxindole by adding acid . The whole synthesis can be carried out as a one-pot reaction without isolation of the intermediate products. The thioether can be easily removed by hydrogenolysis , for example with Raney nickel .

Individual evidence

  1. ^ A b Paul G. Gassman, TJ Van Bergen, Gordon. Gruetzmacher: Use of halogen-sulfide complexes in the synthesis of indoles, oxindoles, and alkylated aromatic amines . In: Journal of the American Chemical Society . tape 95 , no. September 19 , 1973, p. 6508-6509 , doi : 10.1021 / ja00800a088 .
  2. ^ Jie Jack Li: Name reactions . Springer, Berlin 2006, ISBN 978-3-540-30030-4 , pp. 257-258 , doi : 10.1007 / 3-540-30031-7_114 .