The Journal of Organic Chemistry

Direction of cyclization in the Fischer indole synthesis. Mechanistic considerations

FM Miller, WN Schinske

Index: Miller,F.M.; Schinske,W.N. Journal of Organic Chemistry, 1978 ,  vol. 43,  # 17  p. 3384 - 3388            

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Citation Number: 33

Abstract

The effects of acid catalysts and temperature in the uncatalyzed reaction on the direction of cyclization of unsymmetrical ketone phenylhydrazones in the Fischer indole synthesis have been examined. Higher acidity, as previously reported, and higher temperature in the thermal process cause cyclization toward the less substituted position. The observations are considered in terms of a refined version of the first two stages of the mechanism of the ...