Download PDF
Synthesis 2010(21): 3731-3735  
DOI: 10.1055/s-0030-1258218
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Friedel-Crafts Reactions of 2-Naphthol with α-Amido Sulfones and Conversion of the Products with Nucleophiles [¹]

Biswanath Das*, Cheruku Ravindra Reddy, Chava Sindhu, Chithaluri Sudhakar, Siddavatam Nagendra
Organic Chemistry Division-1, Indian Institute of Chemical Technology, Hyderabad 500 007, India
Fax: +91(40)27193198; e-Mail: biswanathdas@yahoo.com;
Further Information

Publication History

Received 6 July 2010
Publication Date:
18 August 2010 (online)

    Permissions and Reprints All articles of this category

Abstract

2-Naphthol underwent Friedel-Crafts reaction with N-benzyloxycarbonylamino sulfones in the presence of InCl3 at room temperature to form the corresponding sulfonyl derivatives in high yields. The products were subsequently reacted with nucleophiles such as allyltributyltin and anisole to replace the sulfonyl group.

Key words

2-naphthol - α-amido sulfone - InCl3 - Friedel-Crafts reaction - nucleophile

1

Part 209 in the series ‘Studies on Novel Synthetic Methodologies’.

    References

  • 2 Shen AY. Tsai CT. Chen CL. Eur. J. Med Chem.  1999,  34:  877 
    CrossrefGoogle Scholar
  • 3a Das B. Laxminarayana K. Ravikanth B. Rao BR.
    J. Mol. Catal. A: Chem.  2007,  261:  180 
    Google Scholar
  • 3b Das B. Veeranjaneyulu B. Krishnaiah M. Balasubramanyam P. Synth. Commun.  2009,  39:  1929 
    Google Scholar
  • 4a Khodaei MM. Khosropour AR. Moghanian H. Synlett  2006,  916 
    Google Scholar
  • 4b Selvam NP. Perumal PT. Tetrahedron Lett.  2006,  47:  7481 
    Google Scholar
  • 4c Srihari G. Nagaraju M. Murthy MM. Helv. Chim. Acta  2007,  90:  1497 
    Google Scholar
  • 4d Shaterian HR. Amirzadeh A. Khorami E. Ghashang M. Synth. Commun.  2008,  38:  2983 
    Google Scholar
  • 4e Mahdavinia GH. Bigdeli MA. Chin. Chem. Lett.  2009,  20:  383 
    Google Scholar
  • 5a Das B. Damodar K. Saritha D. Chowdhury N. Krishnaiah M. Tetrahedron Lett.  2007,  48:  7930 
    Google Scholar
  • 5b Das B. Damodar K. Shashi Kanth B. Srinivas Y. Kalavathi I. Synlett  2008,  3133 
    Google Scholar
  • 5c Das B. Damodar K. Bhunia N. J. Org. Chem.  2009,  74:  5607 
    Google Scholar
  • 6a Pearson WH. Lindbeck AC. Kampf JW. J. Am. Chem. Soc.  1933,  115:  2622 
    Google Scholar
  • 6b Mecozzi T. Petrini M. J. Org. Chem.  1999,  64:  8970 
    Google Scholar
  • 7a Petrini M. Chem. Rev.  2005,  105:  3949 
    Google Scholar
  • 7b Petrini M. Torregiani E. Synthesis  2007,  159 
    Google Scholar
  • 7c Thirupathi P. Kim SS. J. Org. Chem.  2009,  74:  7755 
    Google Scholar
  • 7d Reingruber R. Baumann T. Dabmen S. Bräse S. Adv. Synth. Catal.  2009,  351:  1019 
    Google Scholar
1

Part 209 in the series ‘Studies on Novel Synthetic Methodologies’.