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

 
  • References


    • For excellent reviews, see for example:
    • 1a Farinola GM, Ragni R. Chem. Soc. Rev. 2011; 40: 3467
    • 1b Hu L, Xu G. Chem. Soc. Rev. 2010; 39: 3275
    • 1c Qian G, Zhong Z, Luo M, Yu D, Zhang Z, Wang ZY, Ma D. Adv. Mater. (Weinheim, Ger.) 2009; 21: 111
    • 1d Shinar J, Shinar R. J. Phys. D: Appl. Phys. 2008; 41: 133001
    • 1e Williams JA. G, Wilkinson AJ, Whittle VL. Dalton Trans. 2008; 2081
    • 1f Organic Light Emitting Devices: Synthesis, Properties and Applications. Müllen K, Scherf U. Wiley-VCH; Weinheim: 2006
    • 1g Veinot JG. C, Marks TJ. Acc. Chem. Res. 2005; 38: 632
    • 1h Hughes G, Bryce MR. J. Mater. Chem. 2005; 15: 94
    • 1i Tang CW, VanSlyke SA. Appl. Phys. Lett. 1987; 51: 913

      For excellent reviews, see for example:
    • 2a Huang X, Han S, Huang W, Liu X. Chem. Soc. Rev. 2013; 42: 173
    • 2b Liang M, Chen J. Chem. Soc. Rev. 2013; 42: 3453
    • 2c Schlenker CW, Thompson ME. Chem. Commun. 2011; 47: 3702
    • 2d Delgado JL, Bouit P.-A, Filippone S, Herranz MA, Martin N. Chem. Commun. 2010; 46: 4853
    • 2e Mishra A, Fischer MK. R, Bäuerle P. Angew. Chem. Int. Ed. 2009; 48: 2474
    • 2f Cheng Y.-J, Yang S.-H, Hsu C.-S. Chem. Rev. 2009; 109: 5868
    • 2g Thompson BC, Fréchet JM. J. Angew. Chem. Int. Ed. 2008; 47: 58
    • 2h Günes S, Neugebauer H, Sariciftci NS. Chem. Rev. 2007; 107: 1324
    • 2i Organic Photovoltaics: Concept and Realization . Brabec CJ, Dyakonov V, Parisi J, Sariciftci NS. Springer; Berlin: 2003
    • 2j Peumans P, Yakimov A, Forrest SR. J. Appl. Phys. 2003; 93: 3693

      For excellent reviews, see for example:
    • 3a Wu W, Liu Y, Zhu D. Chem. Soc. Rev. 2010; 39: 1489
    • 3b Klauk H. Chem. Soc. Rev. 2010; 39: 2643
    • 3c Dong H, Wang C, Hu W. Chem. Commun. 2010; 46: 5211
    • 3d Anthony JE. Angew. Chem. Int. Ed. 2008; 47: 452
    • 3e Briseno AL, Mannsfeld SC. B, Jenekhe SA, Bao Z, Xia Y. Mater. Today 2008; 11: 38
    • 3f Facchetti A. Mater. Today 2007; 10: 28
    • 3g Murphy AR, Fréchet JM. J. Chem. Rev. 2007; 107: 1066
    • 3h Mas-Torrent M, Rovira C. Chem. Soc. Rev. 2008; 37: 827
    • 3i Mas-Torrent M, Rovira C. J. Mater. Chem. 2006; 16: 433
    • 3j Sun Y, Liu Y, Zhu D. J. Mater. Chem. 2005; 15: 53
    • 3k Dimitrakopoulos CD, Malenfant PR. L. Adv. Mater. (Weinheim, Ger.) 2002; 14: 100
    • 3l Horowitz G. Adv. Mater. (Weinheim, Ger.) 1998; 10: 365
  • 4 Dostert C, Wanstrath C, Frank W, Müller TJ. J. Chem. Commun. 2012; 48: 7271
    • 5a Gronowitz S, Hörnfeldt A.-B. Thiophenes: Best Synthetic Methods . Elsevier; Oxford: 2004
    • 5b Chadwick DJ, Willbe C. J. Chem. Soc., Perkin Trans. 1 1977; 887
    • 5c Wakefield BJ. The Chemistry of Organolithium Compounds . Pergamon; Oxford: 1974
    • 5d Mallan JM, Bebb RL. Chem. Rev. 1969; 69: 693
    • 5e Gilman H, Shirley D. J. Am. Chem. Soc. 1949; 71: 1870
    • 6a Muschelknautz C, Dostert C, Müller TJ. J. Synlett 2010; 415
    • 6b Shu W, Pellegatti L, Oberli MA, Buchwald SL. Angew. Chem. Int. Ed. 2011; 50: 10665
  • 7 Wang Q, Wei H, Schlosser M. Eur. J. Org. Chem. 1999; 3263