16635-92-0Relevant articles and documents
Two new improved approaches to the synthesis of coumarin-based prodrugs
Zheng, Ailian,Wang, Wei,Zhang, Huijuan,Wang, Binghe
, p. 4237 - 4254 (2007/10/03)
Our laboratory has recently reported the development of a coumarin- based, esterase-sensitive prodrug system for the preparation of prodrugs of amines, peptides, and peptidomimetics. Biological evaluations including animal studies have demonstrated the cl
The Generation and Synthetic Utility of Dianions derived from Benzofurancarboxylic Acids
Buttery, Cheryl D.,Knight, David W.,Nott, Andrew P.
, p. 2839 - 2843 (2007/10/02)
The dianionic species, lithium 2-lithiobenzofuran-3-carboxylate (5) and lithium 3-lithiobenzofuran-2-carboxylate (11b) can be readily generated from the parent acids by reaction with lithium diisopropylamide in tetrahydrofuran at low temperatures.While co
β-Deprotonation by Lithium Di-isopropylamide. Vinyl Carbanions from Oxygen Heterocycles in the Synthesis of Carboxylic Acids in the Benzofuran, Flavone, and Coumarin Series and in the Regiospecific Acylation of 2,6-Dimethylchromone
Costa, Ana M. B. S. R. C. S.,Dean, Francis M.,Jones, Michael A.,Smith, Dennis A.,Varma, Rajender S.
, p. 1224 - 1226 (2007/10/02)
Lithium di-isopropylamide at -70 deg C can remove the α-proton from benzofuran in the absence of activating groups and the β-proton if such groups are present; in flavone and 4-methoxycoumarin β-deprotonation occurs readily and the carbanions are easily carboxylated giving acids not previously accessible, while in 2,6-dimethylchromone β-deprotonation is kinetically favoured allowing 3-acylation to be achieved separately from the conventional acylation at the 2-methyl group.
