Affiliation:
1. QOPNA, Department of Chemistry, University of Aveiro, Campus Universitário de Santiago
2. CICECO - Aveiro Institute of Materials, Department of Chemistry, University of Aveiro
3. UCIBIO, REQUIMTE, Department of Chemistry Sciences, Facultyof Pharmacy, University of Porto
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 6π-azaelectrocyclisation involving an intermediate α,β,γ,δ-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.
Subject
Organic Chemistry,Catalysis
Cited by
4 articles.
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