Beckmann Rearrangement Using Indium(III) Chloride: Synthesis of Substituted Oxazoloquinolines from the Corresponding Ketoximes of 3-Acyl-1H-quinolin-4-ones

ABSTRACT Nitrilium ion intermediates in the Beckmann rearrangement of 3-acyl-4-quinolinone ketoximes, in the presence of InCl 3 , were trapped by the β-hydroxy group of the tautomeric form of the ketoxime giving, predominantly, the corresponding oxazoloquinolines with isooxazoloquinolines formed as...

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Bibliographic Details
Published in:Synthesis (Stuttgart) 2006-05, Vol.2006 (10), p.1599-1612
Main Authors: Yoo, Kwang Ho, Choi, Eun Bok, Lee, Hyeon Kyu, Yeon, Guy Hwan, Yang, Hee Cheol, Pak, Chwang Siek
Format: Article
Language:English
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Summary:ABSTRACT Nitrilium ion intermediates in the Beckmann rearrangement of 3-acyl-4-quinolinone ketoximes, in the presence of InCl 3 , were trapped by the β-hydroxy group of the tautomeric form of the ketoxime giving, predominantly, the corresponding oxazoloquinolines with isooxazoloquinolines formed as minor products.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-2006-926463