One-Pot Synthesis of Isoquinuclidines via 2,6-Diaryl-1,2-dihydropyridines using (E,E)-Cinnamylideneacetophenones as Templates
authors Varandas, PAMM; Rocha, DHA; Paz, FAA; Silva, EMP; Silva, AMS
nationality International
journal SYNTHESIS-STUTTGART
author keywords nitrogen heterocycles; Schiff bases; electrocyclic reactions; microwave chemistry; Diels-Alder reaction
keywords DIELS-ALDER REACTION; AMINO ALCOHOL ORGANOCATALYST; 1,2-DIHYDROPYRIDINES; CHEMISTRY; 6-PI-ELECTROCYCLIZATION; DIHYDROPYRIDINES; OXIDATION; ELECTROCYCLIZATIONS; 1-AZATRIENES; ALKALOIDS
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.
publisher GEORG THIEME VERLAG KG
issn 0039-7881
year published 2018
volume 50
issue 10
beginning page 1965
ending page 1972
digital object identifier (doi) 10.1055/s-0036-1591767
web of science category Chemistry, Organic
subject category Chemistry
unique article identifier WOS:000431026400003
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journal impact factor 2.675
5 year journal impact factor 2.434
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