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Synthesis 2010(8): 1339-1343  
DOI: 10.1055/s-0029-1218678
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Microwave-Assisted Synthesis of Nitro-Substituted Tetrahydropyrido­azepines

Thomas Schultz, Sean C. Turner, Wilfried M. Braje*
Abbott GmbH & Co. KG, Knollstr. 50, 67061 Ludwigshafen, Germany
Fax: +49(621)5892443; e-Mail: wilfried.braje@abbott.com;
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Publication History

Received 7 January 2010
Publication Date:
11 February 2010 (online)

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Abstract

The microwave-assisted condensation of azepan-4-ones with 3,5-dinitro-1-methylpyridin-2-one in the presence of ammonia was found to be a highly efficient method for the synthesis of nitro-substituted tetrahydropyridoazepines. Variation of the substituent at the amino group enables the regioselective synthesis of tetrahydropyrido[3,2-c]azepines and tetrahydropyrido[2,3-d]azepines.

Key words

ketones - condensation - regioselectivity - heterocycles - pyridines

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