Tetrahedron letters

Acid-mediated intramolecular cationic cyclization using an oxygen atom as internal nucleophile: synthesis of substituted oxazolo-, oxazino-and …

J Sikoraiová, Š Marchalı́n, A Daı̈ch, B Decroix

Index: Sikoraiova, Jana; Marchalin, Stefan; Daich, Adam; Decroix, Bernard Tetrahedron Letters, 2002 , vol. 43, # 27 p. 4747 - 4751

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Citation Number: 20

Abstract

Efficient assembly of substituted oxazolo-, oxazino-, and oxazepinoisoindolinones (5–7, 12– 15 and 19) is described in three steps according to an acidic α-oxoamidoalkylation reaction from ready available phthalic anhydride by successive imidation, sodium borohydride reduction and intramolecular cationic cyclization involving N-acyliminium species. The relative stereochemistry accompanying these reactions was also discussed.