5-Aryl-2-(2-hydroxyphenyl)furan-3-carbaldehyde: synthesis and study on its ring-chain tautomerism. Issue 30 (27th July 2016)

• Record Type: Journal Article
• Authors: Ghosh, Jaydip; Biswas, Pritam; Sarkar, Tapas; Drew, Michael G.B.; Bandyopadhyay, Chandrakanta
• Is Part Of: Tetrahedron letters. Volume 57:Issue 30(2016)
• Page Start: 3354
• Page End: 3357
• Publication Date: 2016-07-27
• Subjects: 3-Alkynylchromone -- 1-Benzopyran -- Substituted furans -- Ring-chain tautomerism -- Solvent effect; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.06.069
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: An efficient synthesis of 2, 5-diarylfuran-3-carbaldehydes has been achieved. Solvent and substituent-dependent ring-chain tautomerism is reported. The presence of tautomeric forms is supported by mass spectra. Change in population of the tautomers with time in CDCl3 –D2 O was observed. Abstract: An efficient transformation of 3-(1-alkynyl)chromone1 to 2-(2-hydroxyphenyl)-5-phenylfuran-3-carbaldehyde2 has been accomplished using AgNO3 as catalyst. The ring-chain tautomerism of2 depends on solvent and substituent.