Stereoselective aza Diels-Alder reaction on solid phase: a facile synthesis of hexahydrocinnoline derivatives.
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.
Kiriazis
Alexandros
A
Division of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Helsinki, P. O. Box 56 (Viikinkaari 5 E), FI-00014 Helsinki, Finland.
Rüffer
Tobias
T
Jäntti
Sirkku
S
Lang
Heinrich
H
Yli-Kauhaluoma
Jari
J
D001372:Aza Compounds / Q000737:chemistry*; D006574:Heterocyclic Compounds, 2-Ring / Q000138:chemical synthesis*; D008958:Models, Molecular; D013237:Stereoisomerism
D001372:Aza Compounds; D006574:Heterocyclic Compounds, 2-Ring; C476282:cinnoline