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A One-Pot Diastereoselective Synthesis of 2-[Aryl(hydroxy)methyl]-6-methyl-2H-furo[3,2-c]pyran-3,4-diones: Crystallographic Evidence for the Furanone Ring Closure

Abstract : Novel furopyran-3,4-dione-fused heterocycles have been obtained by a one-pot reaction of -brominated dehydroacetic acid and benzaldehydes under organobase conditions. The prepared 2-[aryl(hydroxy)methyl]-6-methyl-2H-furo[3,2-c]pyran-3,4-diones were fully characterized by 2D NMR spectroscopy and supported by single-crystal X-ray analysis to unequivocally prove the furan-3-one five-membered ring-closure mechanism instead of the dihydroflavanon-3-ol six-membered cyclization which has recently been proposed in the literature.
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https://hal.univ-lorraine.fr/hal-01495208
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Submitted on : Friday, March 24, 2017 - 4:22:56 PM
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Yamina Abdi, Baya Boutemeur-Kheddis, Maamar Hamdi, Oualid Talhi, Filipe A. Almeida Paz, et al.. A One-Pot Diastereoselective Synthesis of 2-[Aryl(hydroxy)methyl]-6-methyl-2H-furo[3,2-c]pyran-3,4-diones: Crystallographic Evidence for the Furanone Ring Closure. SYNLETT, Georg Thieme Verlag, 2015, 26 (12), pp.1749-1754. ⟨10.1055/s-0034-1380214⟩. ⟨hal-01495208⟩

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