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Rearrangements of pyrrole and indole substituted enol esters of cyclohexane‐1,3‐dione
Author(s) -
Oliver James E.,
Lusby William R.,
Waters Rolland M.
Publication year - 1991
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570280618
Subject(s) - chemistry , pyrrole , triethylamine , decarboxylation , aromatization , enol , cyclohexane , chloride , acetic acid , medicinal chemistry , indole test , phenol , organic chemistry , catalysis
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 phenol 9 .