Rearrangements of pyrrole and indole substituted enol esters of cyclohexane‐1,3‐dione | Zendy

Oliver James E. | Zendy; Lusby William R. | Zendy; Waters Rolland M. | Zendy

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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 .

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