One-Pot Pyridinium-Ylide-Assisted Tandem Reaction for the Diastereoselective Synthesis of trans-2,3-Dihydrofuran–Chromone Conjugates

Supratim Das; Subham Mandal; Chhanda Mukhopadhyay

doi:10.1055/a-2532-6077

Synlett, Table of Contents

Synlett
DOI: 10.1055/a-2532-6077

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Emerging Trends in Organic Chemistry: A Focus on India

One-Pot Pyridinium-Ylide-Assisted Tandem Reaction for the Diastereoselective Synthesis of trans-2,3-Dihydrofuran–Chromone Conjugates

Supratim Das

^aDepartment of Chemistry, University of Calcutta, 92 APC Road, Kolkata-700009, India

,

Subham Mandal

^bSchool of Chemical Science, Indian Association for the Cultivation of Science, 2A & 2B Raja S. C Mullick Road, Kolkata-700032, India

,

Chhanda Mukhopadhyay ∗

^aDepartment of Chemistry, University of Calcutta, 92 APC Road, Kolkata-700009, India

› Author Affiliations

Abstract

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Abstract

An efficient procedure for the preparation of novel fused 2,3-dihydrofuran–chromone conjugates was developed with the assistance of a pyridinium ylide generated in situ. Pyridine, a 3-formylchromone, a cyclohexane-1,3-dione, and a phenacyl bromide, with triethylamine acting as a catalyst, underwent a sequential, one-pot, two-step, tandem reaction that proceeded smoothly in aqueous media. ¹H and ¹³C NMR spectroscopy and single-crystal analysis confirmed the diastereoselective synthesis of trans-2,3-dihydrofurans.

Key words

metal-catalyst-free reaction - aqueous medium - dihydrofuran–chromone conjugates - gram-scale preparation - pyridinium ylides - one-pot reaction

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References

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