Lower-Rim-Substituted tert-Butylcalix[4]arenes; Part IX: One-Pot Synthesis of Calix[4]arene-Hydroxamates and Calix[4]arene-Amides

Abstract

A simple method for selective acylation of protected and unprotected hydroxylamines with bis- and tetrakis-substituted p-tert-butylcalix[4]arene-acids through amide bond formation via mixed anhydrides is presented. The first crystal structure of calix-hydroxamate 1 is presented.

Key words

calix[4]arene-hydroxamates - calix[4]arene-amides - synthesis - mixed anhydride method

References

• 1a Nagasaki T. Shinkai S. Matsuda TJ. J. Chem. Soc., Perkin Trans. 1  1990,  2617 
• 1b Nagasaki T. Shinkai S. J. Chem. Soc., Perkin Trans. 2  1991,  1063 
• 2 Dasaradhi L. Stark PC. Huber VJ. Smith PH. Jarvinen GD. Gopalan AS. J. Chem. Soc., Perkin Trans. 2  1997,  1187 
• 3 Hutchinson S. Kearney GA. Horne E. Lynch B. Glennon JD. McKervey MA. Harris SJ. Anal. Chim. Acta  1994,  291:  269 
• 4 Harris SJ, MacManus MG, and Guthrie J. inventors; Eur. Patent  309291.  ; Chem. Abstr. 1989, 111, 117298e
• 5 Hamdi A. Abidi R. Asfari Z. Vicents J. J. Incl. Phenom.  2003,  45:  99 
• 6 Canevet Ch. Libman J. Shanzer A. Angew. Chem., Int. Ed. Engl.  1996,  22:  2657 
• 7 Nagasaki T. Shinkai S. Bull. Chem. Soc. Jpn.  1992,  65:  471 
• 8 Glennon JD. Hutchinson S. Harris SJ. Walker A. McKervey MA. McSweeney CC. Anal. Chem.  1997,  69:  2207 
• 9 Pochini A. Ungaro R. Andreetti GD. Calestani G. Ugozzoli F. J. Incl. Phenom.  1984,  2:  199 
• 10 Arnaud-Neu F. Barrett G. Cremin S. Deasy M. Ferguson G. Harris SJ. Lough AJ. Guerra L. McKervey MA. Schwing-Weill MJ. Schwinte P. J. Chem. Soc., Perkin Trans. 2  1992,  1119 
• 11 Reddy AS. Kumar MS. Reddy GR. Tetrahedron Lett.  2000,  41:  6285 
• 12 Smukste I. Smithrud DB. Tetrahedron  2001,  57:  9555 
• 13 Bocheńska M. Banach R. Zielińska A. Kravtsov VCh. J. Incl. Phenom.  2001,  39:  219 
• 14 Arduini A. Ghidini E. Pochini A. Ungaro R. Andreetti GD. Calestani G. Ugozzoli F. J. Incl. Phenom.  1988,  6:  119 
• 15 Bocheńska M, and Lesińska U. inventors; Polish Pat. Appl.  P0375856. Synthesis of calix[4]arene-hydroxamates and new compounds:
• 16 Iwamoto K. Shinkai S. J. Org. Chem.  1992,  57:  7066 
• 17 Casnati A. Pochini A. Ungaro R. Ugozzoli F. Arnaud F. Fanni S. Schwing MJ. Egberink RJM. de Jong F. Reinhoudt DN. J. Am. Chem. Soc.  1995,  117:  2767 
• 18 Bocheńska M. Zielińska A. Pomecko R. Hubscher-Bruder V. Arnaud-Neu F. J. Incl. Phenom.  2005,  52:  129 
• 19 Scheldrick GM. SHELX-97: Program for the solution and refinement of the crystal structures   University of Göttingen; Germany: 1997. 

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Crystallographic data for the structure of 1 reported in this paper have been deposited with Cambridge Crystallographic Data Centre as supplementary publication No. CCDC-275710 (fwd). Copies of the data can be obtained free of charge on application to CCDC, 12, Union Road, Cambridge, UK (E-mail: [e-mail]).