The Journal of Organic Chemistry

Ring contraction of 2-azidoquinoline and quinoxaline 1-oxides

RA Abramovitch, BW Cue Jr

Index: Abramovitch, Rudolph A.; Cue, Berkeley W. Journal of Organic Chemistry, 1980 , vol. 45, # 26 p. 5316 - 5319

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Citation Number: 22

Abstract

Thermal ring contraction of 2-azidoquinoline 1-oxide with loss of nitrogen did not lead to the desired 2-cyano-1-hydroxyindole. Instead, 2-cyanoisatogen (9), 2, 2'-dicyano-3, 3'-bis [indole](lo), and 2-aminoquinoline 1-oxide (7) were formed. The mechanism is believed to