One-Pot Synthesis of Isoquinuclidines via 2,6-Diaryl-1,2-dihydropyridines using (E,E)-Cinnamylideneacetophenones as Templates

abstract

Diastereoselective Diels-Alder reactions of 2,6-diaryl-1,2-dihydropyridines with N-methylmaleimide afford highly substituted isoquinuclidines in good chemical yield (30-50%). This sequential one-pot synthesis is performed under microwave irradiation and involves, primarily, the synthesis of 2,6-diaryl-1,2-dihydropyridines by a 6-azaelectrocyclisation involving an intermediate -di-unsaturated imine, obtained by condensation of (E,E)-cinnamylideneacetophenones with amines. This procedure easily converts unstable 2,6-diaryl-1,2-dihydropyridines into, otherwise inaccessible, isoquinuclidines without any kind of manipulation.

keywords

DIELS-ALDER REACTION; AMINO ALCOHOL ORGANOCATALYST; 1,2-DIHYDROPYRIDINES; CHEMISTRY; 6-PI-ELECTROCYCLIZATION; DIHYDROPYRIDINES; OXIDATION; ELECTROCYCLIZATIONS; 1-AZATRIENES; ALKALOIDS

subject category

Chemistry

authors

Varandas, PAMM; Rocha, DHA; Paz, FAA; Silva, EMP; Silva, AMS

our authors

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