Rearrangement reaction of 1-ethoxy- and 1-hydroxy-2-phenylindole REARRANGEMENT REACTION OF 1-ETHOXY- AND 1-HYDROXY-2-PHENYLINDOLE (Dedicated to Dr. Albert Padwa on his 75th birthday)

Photoirradiation of 1-ethoxy-2-phenylindole in methanol and the reaction of 1-hydroxy-2-phenylindole with tosyl chloride produced 6-ethoxy- and 6-tosyloxy-2-phenylindoles, respectively, as minor products. The latter was derived to 6-ethoxy-2-phenylindole. The structure is determined by direct comparison of the spectral data with those of the authentic 4-, 5-, 6-, and 7-ethoxy-2-phenylindoles whose syntheses are reported in detail. © 2012 The Japan Institute of Heterocyclic Chemistry.