New synthetic approach to substituted isoindolo[2,1-a]quinoline carboxylic acids via intramolecular Diels-Alder reaction of 4-(N-furyl-2)-4-arylaminobutenes-1 with maleic anhydride |
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| Authors: | Fedor I Zubkov Ekaterina V Boltukhina Roman S Borisov |
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| Institution: | a Organic Chemistry Department, Russian Peoples Friendship University, 6 Miklukho-Maklayia St., 117198 Moscow, Russian Federation
b Center of Drugs Chemistry, All-Russian Institute for Chemical and Pharmaceutical Research, 7 Zubovskaya St., 119815 Moscow, Russian Federation |
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| Abstract: | Acylation of substituted 4-(furyl-2)-4-arylaminobut-1-enes with maleic anhydride provided 2-allyl-6-carboxy-4-oxo-3-aza-10-oxatricyclo5.2.1.01,5]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 °C) promoted cyclic ether opening, intramolecular cyclization and aromatization to give the corresponding tetracyclic compounds, 5,6,6a,11-tetrahydro-10-carboxyisoindolo2,1-a]quinolines, in moderate yields. The influence of the acid and the reaction temperature on the cyclization reactions are also discussed. |
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| 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 01 5]decenes Intramolecular Friedel-Crafts alkylation |
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