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Synthesis 1986; 1986(11): 886-891
DOI: 10.1055/s-1986-31817
DOI: 10.1055/s-1986-31817
paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.
Synthesis of 4-Amino-3-pyridinyl and 4-Amino-5-pyrimidinyl Aryl Ketones and Related Compounds via an ortho-Lithiation Reaction
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Publikationsverlauf
Publikationsdatum:
20. August 2002 (online)
![](https://www.thieme-connect.de/media/synthesis/198611/lookinside/thumbnails/10.1055-s-1986-31817-1.jpg)
4-Chloropyridine and 4,6-dïchloropyrimidine react regioselectively with lithium diisopropylamide to give 4-chloro-3-lithiopyridine and 4,6-dichloro-5-lithiopyrimidine, respectively. These intermediates react with benzaldehydes to give (4-chloro-3-pyridinyl) and 4,6-dichloro-5-pyrimidinyl)-arylmethanols which are oxidized to the corresponding ketones by chromium(VI) oxide in acetone. These compounds ran be nucleophilically substituted with ammonia or primary amines to give 4-amino-3-aroylpyridines or amino-5-aroylpyridines. The 3 aroyl-4-chloropyridines can also be easily converted into 3-aroyl-4(1H)-pyridinones.