83286-36-6

Upstream product

• 83286-30-0 2-(2-furyl)-4,5-dihydro-4,4-dimethyl-1,3-oxazole 
• 100-52-7 benzaldehyde 
• 527-69-5 2-furancarbonyl chloride 
• 88-14-2 2-furanoic acid 
• 83286-35-5 N-(1,1-dimethyl-2-hydroxyethyl)furan-2-carboxamide 

Relevant academic research and scientific papers

Regiospecific Metallation of Furyl-4,5-dihydrooxazoles: Preparation of 2,5-Disubstituted and 2,3,5-Trisubstituted Furans

Regiospecific metallation at C-5 of 2-(2-furyl)-4,4-dimethyl-4,5-dihydrooxazole 1 has been carried out using butyllithium in tetrahydrofuran (THF) and hexamethylphosphoramide (HMPA) as co-solvent.Reaction of the metallated species 1a with various electrophiles allowed us to prepare the disubstituted furans 3 - 13.The metallation of (5-alkyl- or 5-trialkylsilyl-2-furyl)-4,5-dihydrooxazoles 3, 4, 8, 9 or 10 with butyllithium in THF led to regiospecific metallation at C-3 and reaction with electrophiles provided the expected trisubstituted furans.C-3 Lithiation of (5-trialkylsilyl-2-furyl)-4,5-dihydrooxazoles 3 and 4 is a potential route to 2,3-disubstituted furans.All these reactions took place with generally good yields.

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

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.