137777-09-4Relevant articles and documents
The cyanide catalyzed isomerization of enol esters derived from cyclic 1,3-diketones
Montes, Imber Flores,Burger, Ulrich
, p. 1007 - 1010 (1996)
Cross-over experiments unveil that the mechanism of the title reaction consists in cleavage of enol esters by cyanide with transient formation of acyl cyanides. These react as 'soft' C-acylating agents with the enolates freed in the initial step. Use is made of the acyl cyanide derived from pyrrole-2-carboxylic acid to set up the triketide type skeleton 12 of the antibiotic pyoluteorin 16. The aromatization of 12 with mercuric acetate gave the pyrrolo[a]indolone 18.
Rearrangements of Pyrrole and Indole Substituted Enol Esters of Cyclohexane-1,3-dione
Oliver, James E.,Lusby, William R.,Waters, Rolland M.
, p. 1565 - 1568 (2007/10/02)
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.