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Synthesis and Reactivity of Imide-Derived Bisvinyl Phosphates. Reactivity of 2,6-Disubstituted 1,4-Dihydropyridines

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posted on 2006-08-04, 00:00 authored by Deborah Mousset, Isabelle Gillaizeau, Andréa Sabatié,, Pascal Bouyssou, Gérard Coudert
Symmetrical and unsymmetrical 2,6-disubstituted dihydropyridines were prepared in high yields under mild conditions using the Suzuki and Stille Pd-catalyzed coupling reactions of imide-derived bisvinyl phosphates with a range of aryl, heteroaryl, and alkenyl moieties. The alkylation reaction at C-4 easily afforded original tri- and tetrasubstituted dihydropyridines. Hydrolysis of the latter under acidic condition provided efficiently either open-chain 1,5-diketones or di- or trisubstituted pyridines.

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