Stereoselective aza Diels-Alder reaction on solid phase: a facile synthesis of hexahydrocinnoline derivatives |
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Authors: | Kiriazis Alexandros Rüffer Tobias Jäntti Sirkku Lang Heinrich Yli-Kauhaluoma Jari |
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Affiliation: | Division of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Helsinki, P. O. Box 56 (Viikinkaari 5 E), FI-00014 Helsinki, Finland. |
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Abstract: | As part of our continuing studies of polymer-supported pericyclic reactions for preparing biologically interesting heterocyclic compounds, we have introduced a traceless solid-phase synthesis of hexahydrocinnolines. We developed a method in which mild reaction conditions can be used for the hetero-Diels-Alder reactions on a polymeric support. The dienoic 3-vinyl-2-cyclohexenol attached to a Wang resin through an ether linkage undergoes [4 + 2] cycloaddition reaction with several azadienophiles. The highly stereoselective Diels-Alder reaction showed preferential formation of a single cycloadduct resulting from an anti attack of the dienophile on the polymer-bound diene. Trifluoroacetic acid-mediated cleavage of the polymer-bound cycloadducts yields fused nonaromatic hexahydrocinnolines in moderate yields in three steps. |
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