Synthesis of a Library of N-p-Hydroxybenzoyl Thioureas using a Poly(ethylene glycol) Support

Abstract

A library of N-p-hydroxybenzoyl thioureas has been synthesized using poly(ethylene glycol) (PEG) as soluble polymer support. PEG and para-hydroxybenzoic acid were linked by oxalyl chloride to give II. Compound II was acylated by thionyl chloride, followed by esterification with ammonium rhodanate to give IV in which PEG itself also acted as phase-transfer catalyst. Compound IV reacted with R₁R₂NH to yield V. Hydrolysis of V gave VI. This synthetic method is simple and mild, and the yields are moderate to high.

Key words

poly(ethylene glycol) - soluble polymer support - N-p-hydroxybenzoyl thiourea

References

• 1 Früchtel JS. Jung G. Angew. Chem., Int. Ed. Engl.  1996,  35:  17 
• 2 Thompson LA. Ellman JA. Chem. Rev.  1996,  96:  555 
• 3 Yan B. Acc. Chem. Res.  1998,  31:  621 
• 4 Han H. Wolfe MM. Brenner S. Janda KD. Proc. Natl. Acad. Sci. U.S.A.  1995,  92:  6419 
• 5 Wentworth J. Janda KD. Chem.Commun.  1999,  1917 
• 6 Geekeler KE. Adv. Polym. Sci.  1995,  121:  31 
• 7 Sigh B. Yadava BP. Aggarwal RC. Indian J. Chem., Sect. A  1985,  24:  127 
• 8a Josef J. inventors; Czech Patent CS  245,088. 
• 9a Kumar P. Srivastava SK. Ramrakhyani AK. Acta Cienc. Indica, Chem.  1982,  8:  208 
• 10a Uppal KS. Banerji SK. Indian J. Agric. Chem.  1985,  18:  85 
• 11 Chen JC. Wei TB. Wang XC. Yang SY. Chin. Chem. Lett.  1993,  4:  5 
• 12 Reeves WP. Simmoms A. Rudis JA. Bothwell TC. Synth. Commun.  1981,  11:  781 
• 13 Meshkatalsadat MH. Shahsafi MA. Parekh H. Indian J. Chem., Sect. B  1988,  27:  195 
• 14 Mutter M. Hagenmaier H. Bayer E. Angew. Chem., Int. Ed. Engl.  1971,  10:  811 
• 15 Bayer E. Mutter M. Nature  1972,  237:  512 
• 16 Berengere S. Frederic L. Rene L. Jean M. Tetrahedron Lett.  1998,  39:  821 
• 17 Berengere S. Frederic L. Rene L. Jean M. Tetrahedron Lett.  2000,  41:  6371