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Synthesis 2004(12): 1987-1990  
DOI: 10.1055/s-2004-829146
PAPER
© Georg Thieme Verlag Stuttgart · New York

One-Pot Synthesis of 4-Methoxy(aralkoxy)imino-areno[1,3]oxazin-2-ones

Thomas Kurz*, Khalid Widyan, Claudia Wackendorff, Katrin Schlüter
Institute of Pharmacy, University of Hamburg, Bundesstrasse 45, 20146 Hamburg, Germany
Fax: +49(40)428383467; e-Mail: kurz@chemie.uni-hamburg.de;
Further Information

Publication History

Received 2 April 2004
Publication Date:
13 July 2004 (online)

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Abstract

Stepwise treatment of ortho-hydroxy-arenonitriles with 1,1′-carbonyl-di-(1,2,4-triazole) and O-substituted hydroxylamines in the presence of Et3N gave 4-methoxy(aralkoxy)imino-benzo[1,3]oxazin-2-ones and 4-methoxy(aralkoxy)imino-naphtho[2,3-e][1,3]oxazin-2-ones.

Key words

heterocycles - Dimroth rearrangement - ring closure - base-catalyzed - 4-methoxy(aralkoxy)-imino-areno[1,3]oxazin-2-ones

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Crystallographic data for compound 5e has been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 232844. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK [fax: +44(1223)336033 or e-mail: deposit@ccdc.cam.ac.uk].