83286-37-7Relevant academic research and scientific papers
Regioselective β-Metallation of 2-Substituted Furan and N-Methylpyrrole Derivatives Employing the Directing Effect of the Oxazolino Group: Syntheses of 2,3-Disubstituted Furans and N-Methylpyrroles
Chadwick, Derec J.,McKnight, Michael V.,Ngochindo, Raphael
, p. 1343 - 1348 (2007/10/02)
The effects of change of solvent and reaction time, of addition of Li+-chelating agent, and in some instances, of change of temperature and metallating agent, on the metallation of 2-(2-furyl)- and 2-(N-methylpyrrol-2-yl)-oxazolines by alkyl-lithium reagents are explored.Conditions are thereby established for high-yielding syntheses of lithio-intermediates and for control of regioselectivity of metallation.Syntheses of pure samples of 2-(3-hydroxyphenylmethyl-2-furyl)-, 2-(5-hydroxyphenylmethyl-2-furyl)-, 2-(3-carboxy-N-methylpyrrol-2-yl)- and 2-(5-carboxy-N-methylpyrrol-2-yl)-4,4-dimethyloxazolines, based on the results of these investigation, are reported.
