Synthesis 2005(20): 3639-3643  
DOI: 10.1055/s-2005-918450
PAPER
© Georg Thieme Verlag Stuttgart · New York

Sequential Reduction and Dehydration of Phenacyl-(E)-Styryl Sulfones to Unsymmetrical (E,E)-Bis(styryl) Sulfones

Muralidhar Reddy Mallireddigari, Venkat R. Pallela, E. Premkumar Reddy, M. V. Ramana Reddy*
Fels Institute for Cancer Research, Temple University School of Medicine, 3307 North Broad Street, Philadelphia, PA 19140-5101, USA
Fax: +1(215)7071454; e-Mail: rreddy@temple.edu;
Further Information

Publication History

Received 27 January 2005
Publication Date:
27 October 2005 (eFirst)

Abstract

β-Keto vinylic sulfones, the key building blocks for the synthesis of the title compounds, were prepared by two different routes. NaBH4 reduction of these compounds afforded β-hydroxy vinylic sulfones which were dehydrated with acetic anhydride and BF3·Et2O to obtain bis(styryl) sulfones. Alternatively, one-pot synthesis of these bis(styryl) sulfones was also achieved directly from β-keto vinylic sulfones by treating with NaBH4 in EtOH followed by refluxing with concentrated HCl.

    References

  • 1 Truce WE. Klinger TC. Braud WW. Sulfones and Sulfoxides   Oae S. Plenum Press; New York: 1977. 
  • 2 Magnus PD. Tetrahedron  1977,  33:  2019 
  • 3 Block E. Reactions of Organic Sulfur Compounds   Blomquist AT. Wasermann HH. Academic Press; New York: 1978. 
  • 4 Durst T. Comprehensive Organic Chemistry   Vol. 3:  Jones D. Pergamon Press; Oxford: 1979. 
  • 5 Trost BM. Bull. Chem. Soc. Jpn.  1988,  61:  107 
  • 6 Lucchi OD. Pasquato L. Tetrahedron  1988,  44:  6755 
  • 7 Cragg GM. Newman DJ. J. Nat. Prod.  2004,  67:  232 
  • 8 Campbell JA. Chris AVB. Browner MF. Kress JM. Mirzadegan T. Ramesha C. Sanpablo BF. Stabler R. Takahara P. Villasenor A. Walker KAM. Wang JH. Welch M. Weller P. Bioorg. Med. Chem. Lett.  2004,  14:  4741 
  • 9 Fuchs PL. Braish TF. Chem. Rev.  1986,  86:  903 
  • 10 Simpkins NS. Sulphones in Organic Synthesis   Pergamon Press; New York: 1993. 
  • 11 Bertus P. Phansavath P. Ratovelomanana-Vidal V. Genet J.-P. Touati AR. Homri T. Hossine BB. Tetrahedron Lett.  1999,  40:  3175 
  • 12 Gotor V. Rebolledo F. Liz R. Tetrahedron: Asymmetry  2001,  12:  513 
  • 13 Zhao G. Hu J.-B. Qian Z.-S. Yin W.-X. Tetrahedron: Asymmetry  2002,  13:  2095 
  • 14 Pahsavath PB. Ratovelomanana-Vidal V. Genet JP. Touati AR. Hornri T. Hassine BB. Tetrahedron: Asymmetry  1999,  10:  1369 
  • 15 Sato T. Okumura Y. Itai J. Fujisawa T. Chem. Lett.  1988,  1537 
  • 16 Kozikowski AP. Mugrage BB. Li CS. Felder L. Tetrahedron Lett.  1986,  27:  4817 
  • 17 Tanikaga R. Hosoya K. Kaji A. J. Chem. Soc., Perkin Trans. 1  1988,  2397 
  • 18 Tanikaga R. Hosoya K. Kaji A. J. Chem. Soc., Perkin Trans. 1  1987,  1799 
  • 19 Reddy DB. Reddy PVR. Vijayalakshmi S. Reddy MVR. Phosphorus, Sulfur Silicon  1993,  84:  63 
  • 20 Gnanadeepam M. Selvaraj S. Perumal S. Renuga S. Selvaraj S. Phosphorus, Sulfur Silicon Relat. Elem.  2002,  177:  431 
  • 21 Reddy DB. Reddy S. Padmavathi V. Reddy MVR. Sulfur Lett.  1990,  11:  281 
  • 22 Reddy DB. Padmaja A. Reddy PVR. Sulfur Lett.  1993,  16:  227 
  • 23 Padmavathi V. Reddy KV. Balaiah A. Reddy TVR. Reddy DB. Heteroat. Chem.  2002,  13:  677 
  • 24 Reddy MV. Manjubhashini AB. Reddy S. Reddy PVR. Reddy DB. Synth. Commun.  1991,  21:  1589 
  • 25 Reddy DB. Reddy MM. Padmavathi V. Indian J. Heterocycl. Chem.  1995,  5:  11 
  • 26 Gervay-Hague J. Meadows DC. Hadd MJ. Abstracts of Papers, 225 th ACS National Meeting, New Orleans, 2003   American Chemical Society; Washington: 2003. 
  • 27 Reddy EP, and Reddy MVR. inventors; U. S. Patent Appl.,  20020022666A1.  2002; Chem. Abstr. 2002, 136, 183608
  • 28 Kamigata N. Ozaki J. Kobayashi M. J. Org. Chem.  1985,  50:  5045 
  • 29 Reddy DB. Reddy MM. Subbaraju GV. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem.  1995,  34:  816 
  • 30 Melton J. McMurray JE. J. Org. Chem.  1975,  40:  2138 
  • 31 Bartoli G. Bellucci MC. Petrini M. Marcantoni E. Sambri L. Torregiani E. Org. Lett.  2000,  2:  1791 
  • 32 Concellon JM. Rodriguez-Solla H. Mejica C. Tetrahedron Lett.  2004,  45:  2977 
  • 33 Ballini R. Fiorini D. Palmeiri A. Tetrahedron Lett.  2004,  45:  7027