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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ciceco authors
impact metrics
journal analysis (jcr 2019):
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journal impact factor |
2.675 |
5 year journal impact factor |
2.434 |
category normalized journal impact factor percentile |
62.281 |
dimensions (citation analysis):
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altmetrics (social interaction):
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