Synthesis 2016; 48(20): 3544-3550
DOI: 10.1055/s-0035-1562440
paper
© Georg Thieme Verlag Stuttgart · New York

Regioselective Synthesis of 1,2-Benzothiazine 1,1-Dioxide Derivatives by Intramolecular Heck Cyclization

Sudarshan Debnath
b   Department of Chemistry, Visva-Bharati University, Santiniketan 731235, India
,
Suniti Malakar
b   Department of Chemistry, Visva-Bharati University, Santiniketan 731235, India
,
Shovan Mondal*
b   Department of Chemistry, Visva-Bharati University, Santiniketan 731235, India
› Author Affiliations
Further Information

Publication History

Received: 27 March 2016

Accepted after revision: 10 May 2016

Publication Date:
24 June 2016 (online)


Abstract

An efficient method for the synthesis of bioactive heterocycles containing 1,2-benzothiazine 1,1-dioxide derivatives via Pd-catalyzed intramolecular Heck cyclization is reported. The method offers the regioselective synthesis of highly functionalized benzosultams in 80–85% yields. The structure of benzosultam derivatives is confirmed from single crystal X-ray diffraction.

Supporting Information

 
  • References


    • For recent reviews on sultam chemistry, see:
    • 1a Majumdar KC, Mondal S. Chem. Rev. 2011; 111: 7749
    • 1b Scozzafava A, Owa T, Mastrolorenzo A, Supuran CT. Curr. Med. Chem. 2003; 10: 925
    • 1c McReynolds MD, Dougherty JM, Hanson PR. Chem. Rev. 2004; 104: 2239
  • 2 Turck D, Busch U, Heinzel G, Narjes H, Nehmiz G. J. Clin. Pharmacol. 1996; 36: 79
  • 3 Ahmad M, Rizvi SU. F, Siddiqui HL, Ahmad S, Parvez M, Suliman R. Med. Chem. Res. 2012; 21: 2340
  • 4 Wells GJ, Tao M, Josef KA, Bihvsky R. J. Med. Chem. 2001; 44: 3488
  • 5 Wroblewski T, Graul A, Castaner J. Drugs Future 1998; 23: 365
  • 6 Combrink KD, Gulgeze HB, Thuring JW, Yu K.-L, Civiello RL, Zhang Y, Pearce BC, Yin Z, Langley DR, Kadow KF, Cianci CW, Li Z, Clarke J, Genovesi EV, Medina I, Lamb L, Yang Z, Zadjura L, Krystal M, Meanwell NA. Bioorg. Med. Chem. Lett. 2007; 17: 4784
  • 7 Kim SH, Ramu R, Kwon SW, Lee SH, Kim CH, Kang SK, Rhee SD, Bae MA, Ahn SH, Ha DC, Cheon HG, Kim KY, Ahn JH. Bioorg. Med. Chem. Lett. 2010; 20: 1065
  • 8 Wales JK, Krees SV, Grant AM, Vikroa JK, Wolff FW. J. Pharm. Exp. Ther. 1968; 164: 421
    • 9a Reddy AS, Reddy MN, Kumara Swamy KC. RSC Adv. 2014; 4: 28359
    • 9b Yamagishi M, Nishigai K, Ishii A, Hata T, Urabe H. Angew. Chem. Int. Ed. 2012; 51: 6471
  • 10 Pham MV, Ye B, Cramer N. Angew. Chem. Int. Ed. 2012; 51: 10610
  • 11 Liu XY, Li CH, Che CM. Org. Lett. 2006; 8: 2707
  • 12 Ishida N, Shimamoto Y, Yano T, Murakami M. J. Am. Chem. Soc. 2013; 135: 19103
  • 13 Barange DK, Nishad TC, Swamy NK, Bandameedi V, Kumar D, Sreekanth BR, Vyas K, Pal M. J. Org. Chem. 2007; 72: 8547
  • 14 Rayabarapu DK, Zhou A, Jeon KO, Samarakoon T, Rolfe A, Siddiqui H, Hanson PR. Tetrahedron 2009; 65: 3180
  • 15 Miura T, Yamauchi M, Kosaka A, Murakami M. Angew. Chem. Int. Ed. 2010; 49: 4955
  • 16 Siva Reddy A, Kumara Swamy KC. Org. Lett. 2015; 17: 2996
  • 18 CCDC 1458153 contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.