The Journal of Organic Chemistry

Substituent rearrangement and elimination during noncatalyzed Fischer indole synthesis

JE Baldwin, NR Tzodikov

Index: Baldwin,J.E.; Tzodikov,N.R. Journal of Organic Chemistry, 1977 , vol. 42, # 11 p. 1878 - 1883

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Citation Number: 13

Abstract

Treatment of 2, 3, 3-trimethyl-4-pentenal phenylhydrazone in refluxing ethylene glycol led to l-(3-methylbut-2-en-l-y1)-3-methylindole, presumably through allylic rearrangement to the indolic nitrogen of the intermediate 3-(1, l-dimethylallyl)-3-methylindolenine; no rearrangement to a 4-allylindole derivative was observed. Treatment of 1.3- cyclohexanedione-2-chloro-6-(3-methylbut-2-en-l-y1) phenylhydrazone in refluxing o- ...