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

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.

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

References

1

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

2 Shen AY. Tsai CT. Chen CL. Eur. J. Med Chem.  1999,  34:  877 

3a Das B. Laxminarayana K. Ravikanth B. Rao BR.
J. Mol. Catal. A: Chem.  2007,  261:  180 

3b Das B. Veeranjaneyulu B. Krishnaiah M. Balasubramanyam P. Synth. Commun.  2009,  39:  1929 

4a Khodaei MM. Khosropour AR. Moghanian H. Synlett  2006,  916 

4b Selvam NP. Perumal PT. Tetrahedron Lett.  2006,  47:  7481 

4c Srihari G. Nagaraju M. Murthy MM. Helv. Chim. Acta  2007,  90:  1497 

4d Shaterian HR. Amirzadeh A. Khorami E. Ghashang M. Synth. Commun.  2008,  38:  2983 

4e Mahdavinia GH. Bigdeli MA. Chin. Chem. Lett.  2009,  20:  383 

5a Das B. Damodar K. Saritha D. Chowdhury N. Krishnaiah M. Tetrahedron Lett.  2007,  48:  7930 

5b Das B. Damodar K. Shashi Kanth B. Srinivas Y. Kalavathi I. Synlett  2008,  3133 

5c Das B. Damodar K. Bhunia N. J. Org. Chem.  2009,  74:  5607 

6a Pearson WH. Lindbeck AC. Kampf JW. J. Am. Chem. Soc.  1933,  115:  2622 

6b Mecozzi T. Petrini M. J. Org. Chem.  1999,  64:  8970 

7a Petrini M. Chem. Rev.  2005,  105:  3949 

7b Petrini M. Torregiani E. Synthesis  2007,  159 

7c Thirupathi P. Kim SS. J. Org. Chem.  2009,  74:  7755 

7d Reingruber R. Baumann T. Dabmen S. Bräse S. Adv. Synth. Catal.  2009,  351:  1019