Synlett 2014; 25(3): 371-374
DOI: 10.1055/s-0033-1340307
letter
© Georg Thieme Verlag Stuttgart · New York

2,6-Difunctionalization of N-Substituted Dithienothiazines via Dilithiation

Catherine Dostert
Institut für Organische Chemie und Makromolekulare Chemie der Heinrich-Heine-Universität Düsseldorf, Universitätsstr. 1, 40225 Düsseldorf, Germany   Fax: +49(211)8114324   Email: ThomasJJ.Mueller@uni-duesseldorf.de
,
Daniel Czajkowski
Institut für Organische Chemie und Makromolekulare Chemie der Heinrich-Heine-Universität Düsseldorf, Universitätsstr. 1, 40225 Düsseldorf, Germany   Fax: +49(211)8114324   Email: ThomasJJ.Mueller@uni-duesseldorf.de
,
Thomas J. J. Müller*
Institut für Organische Chemie und Makromolekulare Chemie der Heinrich-Heine-Universität Düsseldorf, Universitätsstr. 1, 40225 Düsseldorf, Germany   Fax: +49(211)8114324   Email: ThomasJJ.Mueller@uni-duesseldorf.de
› Author Affiliations
Further Information

Publication History

Received: 17 October 2013

Accepted after revision: 31 October 2013

Publication Date:
13 November 2013 (online)


Abstract

The regioselective lithiation of dithienothiazines followed by electrophilic trapping in a one-pot fashion is an efficient route to 2-mono- and 2,6-difunctionalized dithienothiazines. A pseudo five-component dilithiation–diformylation–double-Wittig olefination sequence gives a dithienothiazine symmetrically functionalized with α,β-unsaturated ester side chains in excellent yield.

Supporting Information