Unexpected Heteroannulation and Chlorination of Benzothiadiazine Derivatives Mediated by DDQ

Valerie Verones; Nathalie Flouquet; Amaury Farce; Pascal Berthelot; Nicolas Lebegue

doi:10.1055/s-0033-1340249

Synthesis, Table of Contents

Synthesis 2014; 46(02): 235-241
DOI: 10.1055/s-0033-1340249

paper

Unexpected Heteroannulation and Chlorination of Benzothiadiazine Derivatives Mediated by DDQ

Valerie Verones

Laboratoire de Chimie Thérapeutique, UFR Pharmacie Univ Lille Nord de France, 59000 Lille, France Fax: +33(3)20964913 Email: nicolas.lebegue@univ-lille2.fr

,

Nathalie Flouquet

Laboratoire de Chimie Thérapeutique, UFR Pharmacie Univ Lille Nord de France, 59000 Lille, France Fax: +33(3)20964913 Email: nicolas.lebegue@univ-lille2.fr

,

Amaury Farce

Laboratoire de Chimie Thérapeutique, UFR Pharmacie Univ Lille Nord de France, 59000 Lille, France Fax: +33(3)20964913 Email: nicolas.lebegue@univ-lille2.fr

,

Pascal Berthelot

Laboratoire de Chimie Thérapeutique, UFR Pharmacie Univ Lille Nord de France, 59000 Lille, France Fax: +33(3)20964913 Email: nicolas.lebegue@univ-lille2.fr

,

Nicolas Lebegue*

Laboratoire de Chimie Thérapeutique, UFR Pharmacie Univ Lille Nord de France, 59000 Lille, France Fax: +33(3)20964913 Email: nicolas.lebegue@univ-lille2.fr

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Abstract

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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 - diastereoselectivity

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References

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Supplementary Material

Supporting Information