Tetrahedron p. 10323 - 10342 (1995)
Update date:2022-08-03
Topics:
Wensbo, David
Annby, Ulf
Gronowitz, Salo
Bz-substituted indole-3-acetic acid ethyl esters (14e-g) and heteroanalogues, i.e. thienopyrroles (14a,c) and selenolopyrrole (14d), were prepared starting from N-BOC protected o-iodo aryl amines. Allylation with ethyl 4-bromocrotonate, followed by palladium-catalysed ring closure in a one pot reaction, yielded N-BOC protected indoles (13e-g), thienopyrroles (13a-c), and selenolopyrrole (13d). The BOC group was readily removed thermally after adsorption on silica. Oxothienopyrroles (11a-c) were similarly prepared.
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