Journal
TETRAHEDRON
Volume 61, Issue 16, Pages 4099-4113Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2005.02.017
Keywords
homoallylamines (4-(furyl-2)-4-N-arylaminobut-1-enes); intramolecular furan Diels-Alder reaction (IMDAF); isoindolo[2,1-a]quinolines; 3-aza-10-oxatricyclo[5.2.1.0(1,5)]decenes; intramolecular Friedel-Crafts alkylation
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Acylation of substituted 4-(fury/-2)-4-arylaminobut-1-enes with maleic anhydride provided 2-ally/-6-carboxy-4-oxo-3-aza-10-oxatricyclo[5.2.1.0(1,5)]dec-8-enes in high yield under mild reaction conditions. The Diels-Alder adducts are formed via an initial amide formation followed by a stereoselective intramolecular [4+2] exo-cycloaddition reaction. Treatment of the tricyclic compounds with phosphoric acid at high temperatures (70-120 degrees C) promoted cyclic ether opening, intramolecular cyclization and aromatization to give the corresponding tetracyclic compounds, 5,6,6a,11-tetrahydro-10-carboxyisoindolo[2,1-a]quinolines, in moderate yields. The influence of the acid and the reaction temperature on the cyclization reactions are also discussed. (c) 2005 Elsevier Ltd. All rights reserved.
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