Tetrahedron

General synthetic approach towards annelated 3a, 6-epoxyisoindoles by tandem acylation/IMDAF reaction of furylazaheterocycles. Scope and limitations

…, VN Khrustalev, RA Novikov, DN Orlova, AV Varlamov

Index: Zubkov, Fedor I.; Nikitina, Eugenia V.; Galeev, Timur R.; Zaytsev, Vladimir P.; Khrustalev, Victor N.; Novikov, Roman A.; Orlova, Daria N.; Varlamov, Alexey V. Tetrahedron, 2014 , vol. 70, # 8 p. 1659 - 1690

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Citation Number: 16

Abstract

Abstract An efficient and versatile one-pot synthesis of 3, 6a-epoxyisoindoles annelated with oxazine, oxazole, thiazine, thiazole, pyrimidine fragments and with their benzoannelated analogues is presented. The method is based on tandem N-acylation/intramolecular cycloaddition (the intramolecular Diels–Alder reaction of furan, IMDAF) reaction between α, β-unsaturated acid anhydrides and α-furyl substituted azaheterocycles. The latter can be ...