Tetrahedron

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 …

…, EV Boltukhina, KF Turchin, RS Borisov, AV Varlamov

Index: Zubkov, Fedor I.; Boltukhina, Ekaterina V.; Turchin, Konstantin F.; Borisov, Roman S.; Varlamov, Alexey V. Tetrahedron, 2005 , vol. 61, # 16 p. 4099 - 4113

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Citation Number: 34

Abstract

Acylation of substituted 4-(furyl-2)-4-arylaminobut-1-enes with maleic anhydride provided 2- allyl-6-carboxy-4-oxo-3-aza-10-oxatricyclo [5.2. 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 ...