Synthesis of indolines, indoles, and benzopyrrolizidinones from simple aryl azides.
A simple approach to prepare indolines and benzopyrrolizidinones from ortho-azidoallylbenzenes via a tandem radical addition/cyclization is described. The use of triethylborane to initiate and sustain the process provides the best results. Indolines are easily converted into the corresponding indoles by oxidation with manganese dioxide.
Universität Bern, Departement für Chemie und Biochemie, Freiestrasse 3, CH-3012 Bern, Switzerland.
François
F
Brucelle
Philippe
P
Renaud
D001386:Azides / Q000737:chemistry*; D001554:Benzene / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011763:Pyrrolizidine Alkaloids / Q000138:chemical synthesis*
D001386:Azides; D007211:Indoles; D011763:Pyrrolizidine Alkaloids; C057812:indoline; D001554:Benzene