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Paper | Special issue | Vol 84, No. 2, 2012, pp.785-799
Published online, 16th August, 2011
DOI: 10.3987/COM-11-S(P)56
Rearrangement Reaction of 1-Ethoxy- and 1-Hydroxy-2-phenylindole

Koji Yamada and Masanori Somei*

*Faculty of Pharmaceutical Scicences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma, Kanazawa, Ishikawa 920-1192,


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.