Diastereoselective synthesis of furopyranopyridine in ionic liquid/water without additional catalyst?

RSC Advances Pub Date: 2013-06-11 DOI: 10.1039/C3RA42159G

Abstract

3,5-Diarylidene-1-methyl-piperidin-4-one derived in situ from N-methylpiperidinone and benzaldehyde undergoes intermolecular [4 + 2] hetero-Diels–Alder reactions with 2,3-dihydrofuran in [bmim]BF4H2O (1?:?1) to afford furopyranopyridine derivatives in high to quantitative yields. Heterodienes, 3,5-diaryldiene-1-methylpiperidin-4-one an electron deficient oxadiene added to 2,3-dihydrofuran an electron rich dienophile because of an inverse electron demand, yielding furopyranopyridines with a high atom economy.

Graphical abstract: Diastereoselective synthesis of furopyranopyridine in ionic liquid/water without additional catalyst
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