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Communication | Regular issue | Vol 1, No. 3, 1973, pp.227-231
Published online, 1st January, 1970
DOI: 10.3987/R-1973-03-0227
Ring Contraction of 2-Azidoquinoline- and Quinoxaline-1-oxodes

Rudolph A. Abramovitch* and Berkeley W. Cue, Jr.

*Department of Chemistry, University of Alabama, Box 870336, University, Tuscaloosa, Alabama 35478-0336, U.S.A.


2-Azidoquinoline-1-oxide undergoes thermal ring-opening, intermolecular nucleophilic addition and ring contraction to give 2-aminoquinoline-1-oxide, 2-cyanoisatogen (4), and 2,2’-dicyano- 3,3’-bisindole (5). If the 4-position in the quinoline is blocked then the expected ring-contractions take place: 2-azidolepidine-1-oxide gives 2-cyano-N-hydroxy-3-methylindole, while 2-azidoquinoxaline-1-oxide gives 2-cyano-1-hydroxybenzimidazole. Syntheses of authentic 4 and 5 are reported.