Methoxide ion mediated reactions of methyl azidoacetate with 4‐and 2‐cyanobenzaldehyde. An unexpected cyclization of the ortho isomer to a 2(1H)‐benzazepine derivative

Abstract

AbstractA condensation reaction of 4‐cyanobenzaldehyde (1) with methyl azidoacetate (2) in the presence of sodium methoxide produces a mixture of geometrical isomers of azidocinnamates 3 which undergoes thermolysis to give an indole 4. By contrast, the treatment of 2‐cyanobenzaldehyde (5) with 2 in the presence of sodium methoxide and followed by the usual workup furnishes an azepine derivative 6.