Rearrangements of pyrrole and indole substituted enol esters of cyclohexane??1, 3??dione

JE Oliver, WR Lusby, RM Waters

Index: Oliver, James E.; Lusby, William R.; Waters, Rolland M. Journal of Heterocyclic Chemistry, 1991 , vol. 28, # 6 p. 1565 - 1568

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Citation Number: 8

Abstract

Abstract Enol esters 3a and 3b, from cyclohexane-1, 3-dione and pyrrole-2-carbonyl chloride and indole-2-carbonyl chloride, respectively, rearranged in the presence of triethylamine to the enamino acids 7 and 12. In the presence of cyanide, 3b, also underwent the expected rearrangement to 4b, whereas only 7 was formed from 3a. Treatment of 7 with mercuric acetate in hot acetic acid resulted in decarboxylation and aromatization to ...