Tetrahedron

Synthesis of Novel 3-Acyloxy-1, 3-dihydro-2H-indol-2-ones and Isomeric 4-Acyl-1, 4-dihydro-3, 1-benzoxazin-2-ones: Double Rearrangement of 3-Hydroxyquinoline-2 …

A Klásek, K Kořistek, J Polis, J Košmrlj

Index: Klasek, Antonin; Koristek, Kamil; Polis, Jiri; Kosmrlj, Janez Tetrahedron, 2000 , vol. 56, # 11 p. 1551 - 1560

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Citation Number: 46

Abstract

Substituted 3-hydroxyquinoline-2, 4 (1H, 3H)-diones 3 were transformed into 3-acyloxy-1, 3- dihydro-2H-indol-2-ones 4 and isomeric 4-acyl-1, 4-dihydro-3, 1-benzoxazin-2-ones 5. The influence of the substituents and the reaction conditions on the course of the reaction was studied. In the proposed mechanism a double rearrangement takes place; α-ketol rearrangement of 3, leading to α-hydroxy-β-diketone intermediate 8, is followed by a ...