Synthesis 2011(2): 303-315  
DOI: 10.1055/s-0030-1258352
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis and Characterization of Donor-Functionalized N,S-Compounds Containing the ortho-Aminothiophenol Motif

Edward D. Cross, Usman A. Shehzad, Samantha M. Lloy, Adam R. C. Brown, Todd D. Mercer, Daniel R. Foster, Beth L. McLellan, Alexander R. Murray, Margaret A. English, Matthias Bierenstiel*
Department of Chemistry, Cape Breton University, 1250 Grand Lake Road, Sydney, NS, B1P 6L2, Canada
Fax: +1(902)5631899; e-Mail: matthias_bierenstiel@cbu.ca;
Further Information

Publication History

Received 5 October 2010
Publication Date:
03 December 2010 (eFirst)

Abstract

A series of twenty S-benzyl ortho-aminothiophenol and S,S′-xylylene-bridged bis(ortho-aminothiophenol) compounds and their imine derivatives have been synthesized in moderate to excellent yields and characterized. The syntheses were optimized, including large-scale syntheses, and an improved purification method involving the HCl salt was developed. This paper also serves as a comprehensive review of xylylene-bridged bis(ortho-amino­thiophenol) compounds.

    References

  • 1 Hofmann AW. Ber.  1887,  20:  1788 
  • 2 Schiff H. Justus Liebigs Ann. Chem.  1864,  131:  118 
  • 3 Parveen S. Khan MOF. Austin SE. Croft SL. Yardley V. Rock P. Douglas KT. J. Med. Chem.  2005,  48:  8087 
  • 4 Yang Q. Chen L. He X. Gao Z. Shen X. Bai D. Chem. Pharm. Bull.  2008,  56:  1400 
  • 5 Ham J. Cho SJ. Ko J. Chin J. Kang H. J. Org. Chem.  2006,  71:  5781 
  • 6 Papenfuhs T. inventors; EP  1986-110101.  1986; Chem. Abstr. 1987, 106, 119446
  • 7 Schwindt J, Groegler G, and Recker K. inventors; DE  2509404.  1976; Chem. Abstr. 1976, 85, 192341
  • 8 Chou C.-H. Yu P.-C. Wang B.-C. Tetrahedron Letters  2008,  49:  4145 
  • 9 Schwindt J, Groegler G, and Recker K. inventors; DE  2509405.  1976; Chem. Abstr. 1976, 85, 178763
  • 10 Groeger G, Schwindt J, and Meyborg H. inventors; DE  2635400.  1978; Chem. Abstr. 1978, 88, 154034
  • 11 Bayer E. Fiedler H. Hock KL. Otterbach D. Schenk G. Voelter W. Angew. Chem. Int. Ed.  1964,  3:  325 
  • 12 Haber F. Angew. Chem.  1927,  40:  303 
  • 13 Gao W. Ekstrom J. Liu J. Chen C. Eriksson L. Weng L. Akermark B. Sun L. Inorg. Chem.  2007,  46:  1981 
  • 14 Messaoudi S. Robert V. Guihery N. Maynau D. Inorg. Chem.  2006,  45:  3212 
  • 15 Jayapal P. Sunderarajan M. Hillier IH. Burton NA. Phys. Chem. Chem. Phys.  2006,  8:  4086 
  • 16 Ghosh P. Stobie K. Bill E. Bothe E. Weyhermüller T. Ward MD. McCleverty JA. Wieghardt K. Inorg. Chem.  2007,  46:  522 
  • 17 Ghosh P. Bill E. Weyhermüller T. Neese F. Wieghardt K. J. Am. Chem. Soc.  2003,  125:  1293 
  • 18 Ghosh P. Begum A. Bill E. Weyhermüller T. Wieghardt K. Inorg. Chem.  2003,  42:  3208 
  • 19 Herebian D. Bothe E. Bill E. Weyhermüller T. Wieghardt K. J. Am. Chem. Soc.  2001,  123:  10012 
  • 20 Gok Y. Karabocek S. Karabocek N. Atalay Y. New J. Chem.  1995,  19:  1275 
  • 21 Pal S. Mukherjee G. Poddar SN. Transition Met. Chem.  1994,  19:  99 
  • 22 Maji M. Ghosh S. Chattopadhyay SK. Transition Met. Chem.  1998,  23:  261 
  • 23 Butin KP. Moiseeva AA. Beloglazkina EK. Chudinov YB. Chizhevskii AA. Mironov AV. Tarasevich BN. Lalov AV. Zyk NV. Russ. Chem. Bull.  2005,  54:  173 
  • 24 Basuli F. Chattopadhyay P. Sinha C. Polyhedron  1996,  15:  2439 
  • 25 Chattopadhyay P. Sinha C. Polyhedron  1994,  13:  2689 
  • 26 Bag K. De N K. Das D. Sinha C. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem.  1997,  36:  232 
  • 27 Pal S. Poddar SN. Mukherjee G. Transition Met. Chem.  1994,  19:  449 
  • 28 Ocak Ü. Alp H. Gökce P. Ocak M. Sep. Sci. Technol.  2006,  41:  391 
  • 29 Alp H. Biyikhoglu Z. Ocak M. Ocak . Kantekin H. Dilber G. Sep. Sci. Technol.  2007,  42:  835 
  • 30 Kumar S. Bhalla V. Singh H. Tetrahedron  1998,  54:  5575 
  • 31 Matthews RW. McPartlin M. Scowen IJ. J. Chem. Soc., Dalton Trans.  1997,  2861 
  • 32 Zheng Y. Wang SL. Acta Crystallogr., Sect. C: Cryst. Struct. Commun.  2004,  60:  M278 
  • 33 Kumar S. Kaur S. Singh H. J. Inclusion Phenom. Macrocyclic Chem.  2001,  39:  277 
  • 34 Rajakumar P. Rasheed AMA. Tetrahedron  2005,  61:  5351 
  • 35 Singh P. Kumar S. J. Inclusion Phenom. Macrocyclic Chem.  2007,  59:  155 
  • 36 Kumar S. Singh P. Kaur S. Tetrahedron  2007,  63:  11724 
  • 37 Ishikawa Y. Terao Y. Suzuki K. Shikano N. Sekiya M. Chem. Pharm. Bull.  1984,  32:  438 
  • 39 Marat K. SpinWorks 3.1.7   University of Manitoba; Canada: 2010. 
  • 40 Martin JS. Quirt AR. J. Magn. Reson.  1971,  5:  318 
  • 41 Hamaker CG. Halbach DP. Inorg. Chim. Acta  2006,  359:  846 
  • 42 Hamaker CG. Halbach DP. Polyhedron  2009,  28:  2228 
  • 43 Fakhraian H. Nafary Y. Chalabi H. Res. Chem. Intermed.  2009,  35:  555 
  • 44 Uhlemann E. Pohl V. Z. Anorg. Allg. Chem.  1973,  397:  162 
  • 45 Gotthart H. Hoffmann N. Liebigs Ann. Chem.  1985,  529 
  • 46 Palmer PJ. Trigg RB. Warrington JV. J. Med. Chem.  1971,  14:  248 
  • 47 Jadamus H. Fernando Q. Freiser H. J. Am. Chem. Soc.  1964,  86:  3056 
  • 48 Jadamus H. Fernando Q. Freiser H. Inorg. Chem.  1964,  3:  928 
38

Sigma-Aldrich Catalogue, 2010.