A radical based addition–elimination route for the preparation of indoles
作者:John A. Murphy、Karen A. Scott、Rhona S. Sinclair、Concepcion Gonzalez Martin、Alan R. Kennedy、Norman Lewis
DOI:10.1039/b002565h
日期:——
Indoles, including tricyclic derivatives, are produced by cyclisations of aryl radicals onto vinyl halides followed by elimination of halide radical and tautomerism of the resulting product; the aryl radicals are produced using âclean methodologyâ either by reaction of iodide ions with arenediazonium salts or by reaction of phosphorus-centred radicals with aryl iodides.
The two isomeric dibromides, obtained by the addition of bromine to cyclonona-1,2-diene (4), have been identified as 2,3-dibromo-cis-cyclononene (2; RBr) and 1,4-dibromo-cis-cyclononene (5; RBr); these compounds were obtained in the approximate relative proportions of 40:60.