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Synthesis 2012(10): 1477-1480  
DOI: 10.1055/s-0031-1289713
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© Georg Thieme Verlag Stuttgart ˙ New York

A Convenient Metal-Free Method for the Synthesis of Benzothiazolethiones from o-Haloanilines and Carbon Disulfide

Peng Zhaoa, Fei Wanga, Chanjuan Xi*a,b
a Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084, China
e-Mail: cjxi@tsinghua.edu.cn;
b State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China
Further Information

Publication History

Received 30 December 2011
Publication Date:
16 February 2012 (online)

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Abstract

A convenient method has been developed for the preparation of a variety of 1,3-benzothiazole-2(3H)-thiones. The reaction proceeds from an o-haloaniline derivative and carbon disulfide in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene at 80-140 ˚C to give the corresponding 1,3-benzothiazole-2(3H)-thione derivatives in good-to-excellent yields.

Key words

cyclizations - heterocycles - benzothiazoles - amines - carbon disulfide - tandem reaction

    References

  • These compounds can exist in two tautomeric forms: the 1,3-benzothiazole-2(3H)-thione or the 1,3-benzothiazole-2-thiol. X-ray determination and calculation suggest that the 1,3-benzothiazole-2(3H)-thione tautomer is generally favored; see:
  • 1a Curtiss LA. Redfern PC. Raghavachari K. Pople JA. J. Chem. Phys.  2001,  114:  108 
    Google Scholar
  • 1b Steudel R. Steudel Y. Chem. Eur. J.  2006,  12:  8589 
    Google Scholar
  • 1c Radha A. Z. Kristallogr.  1985,  171:  225 
    Google Scholar
  • 2a Zhang L. Fan J. Vu K. Hong K. Le Brazidec J.-Y. Shi J. Biamonte M. Busch DJ. Lough RE. Grecko R. Ran Y. Sensintaffar JL. Kamal A. Lundgren K. Burrows FJ. Mansfield R. Timony GA. Ulm EH. Kasibhatla SR. Boehm MF. J. Med. Chem.  2006,  40:  5352 
    Google Scholar
  • 2b Dumas J. Brittelli D. Chen J. Dixon B. Hatoum-Mokdad H. König G. Sibley R. Witowsky J. Wong S. Bioorg. Med. Chem. Lett.  1999,  9:  2531 
    Google Scholar
  • 2c Franchini C. Muraglia M. Corbo F. Florio MA. Di Mola A. Rosato A. Matucci R. Nesi M. Bambeke F. Vitali C. Arch. Pharm. (Weinheim, Ger.)  2009,  342:  605 
    Google Scholar
  • 2d Cressier D. Prouillac C. Hernandez P. Amourette C. Diserbo M. Lion C. Rima G. Bioorg. Med. Chem.  2009,  17:  5275 
    Google Scholar
  • 2e Jiang L.-L. Tan Y. Zhu X.-L. Wang Z.-F. Zuo Y. Chen Q. Xi Z. Yang G.-F. J. Agric. Food Chem.  2010,  58:  2643 
    Google Scholar
  • 3a Demartin F. Deplano P. Devillanova FA. Isaia F. Lippolis V. Verani G. Inorg. Chem.  1993,  32:  3694 
    Google Scholar
  • 3b Katkova MA. Borisov AV. Fukin GK. Baranov EV. Averyushkin AS. Vitukhnovsky AG. Bochkarev MN. Inorg. Chim. Acta  2006,  359:  4289 
    Google Scholar
  • 3c Mishra L. Vilaplana R. Singh VK. Yadaw AK. González-Vilchez FJ. Inorg. Biochem.  2001,  86:  581 
    Google Scholar
  • 4a Teppema J. Sebrell LB. J. Am. Chem. Soc.  1927,  49:  1779 
    Google Scholar
  • 4b Teppema J. Sebrell LB. J. Am. Chem. Soc.  1927,  49:  1748 
    Google Scholar
  • 4c Sebrell LB. Boord CE. J. Am. Chem. Soc.  1923,  45:  2390 
    Google Scholar
  • 4d Ballabeni M. Ballini R. Bigi F. Maggi R. Parrini M. Predieri G. Sartori G. J. Org. Chem.  1999,  64:  1029 
    Google Scholar
  • 4e Zhu N. Zhang F. Liu G. J. Comb. Chem.  2010,  12:  531 
    Google Scholar
  • 5a Huang W. Tan Y. Ding M.-W. Yang G.-F. Synth. Commun.  2007,  37:  369 
    Google Scholar
  • 5b Zhu L. Zhang M. Dai M.
    J. Heterocycl. Chem.  2005,  42:  727 
    Google Scholar
  • 5c Harizi A. Romdhane A. Mighri Z. Tetrahedron Lett.  2000,  41:  5833 
    Google Scholar
  • 5d Karlsson HJ. Lincoln P. Westman G. Bioorg. Med. Chem.  2003,  11:  1035 
    Google Scholar
  • 5e Zhu L. Zhang M. J. Org. Chem.  2004,  69:  7371 
    Google Scholar
  • 5f Chaudhuri NC. Synth. Commun.  1996,  26:  3783 
    Google Scholar
  • 5g Singh B. Pennock PO. Lesher GY. Bacon ER. Page DF. Heterocycles  1993,  36:  133 
    Google Scholar
  • 5h Ma D. Lu X. Shi L. Zhang H. Jiang Y. Liu X. Angew. Chem. Int. Ed.  2011,  50:  1118 
    Google Scholar
  • 6a Wang F. Cai S. Wang Z. Xi C. Org. Lett.  2011,  13:  3202 
    Google Scholar
  • 6b Wang F. Zhao P. Xi C. Heterocycles  2012,  84:  209 
    Google Scholar
  • 7a Corban GJ. Hadjikakou SK. Tsipis AC. Kubickl M. Bakas T. Hadjiliadis N. New J. Chem.  2011,  35:  213 
    Google Scholar
  • 7b Espinoza-Fonseca LM. Trujillo-Ferrara JG. Biochem. Biophys. Res. Commun.  2005,  328:  922 
    Google Scholar
  • 8 Časar Z. Lorcy D. Leban I. Maréchal AM.-L. Acta Chim. Slov.  2002,  49:  871 
    Google Scholar
  • 9a Xie J.-G. Quan J. Li S.-B. Zheng Y. Zhu L.-M. Synth. Commun.  2011,  41:  871 
    Google Scholar
  • 9b Rani BR. Bhalerao UT. Rahman MF. Synth. Commun.  1990,  20:  3045 
    Google Scholar