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-2,4(1H,3H)-diones

Authors
Klasek, A Koristek, K Polis, J Kosmrlj, J
Citation
A. Klasek et al., 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-2,4(1H,3H)-diones, TETRAHEDRON, 56(11), 2000, pp. 1551-1560
Citations number
31
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
56
Issue
11
Year of publication
2000
Pages
1551 - 1560
Database
ISI
SICI code
0040-4020(20000310)56:11<1551:SON3AI>2.0.ZU;2-6
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-b enzoxazin-2-ones 5. The influence of the substituents and the reaction cond itions on the course of the reaction was studied. In the proposed mechanism a double rearrangement takes place; alpha-ketol rearrangement of 3, leadin g to alpha-hydroxy-beta-diketone intermediate 8, is followed by a rearrange ment to the isomeric alpha-ketol-esters 4 and 5. (C) 2000 Elsevier Science Ltd. All rights reserved.