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Synthesis 2014; 46(02): 235-241
DOI: 10.1055/s-0033-1340249
DOI: 10.1055/s-0033-1340249
paper
Unexpected Heteroannulation and Chlorination of Benzothiadiazine Derivatives Mediated by DDQ
Further Information
Publication History
Received: 09 September 2013
Accepted after revision: 21 October 2013
Publication Date:
14 November 2013 (online)
Abstract
In the course of studies directed toward the synthesis of new tubulin polymerization inhibitors, several benzothiadiazine derivatives were prepared. The oxidative dehydrogenation reaction with DDQ unexpectedly led to heteroannulation and chlorination of the benzothiadiazine tricycles. A rationale for their formation is proposed.
Key words
benzothiadiazine - oxidative dehydrogenation - heteroannulation - radical reaction - diastereoselectivitySupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
-
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