Abstract
Eight transition metal complexes of various Schiff bases supported on poly(vinyl chloride) (PVC) were prepared and characterized. These metal complexes were screened as heterogeneous catalysts in the synthesis of β-amino alcohols by ring opening of epoxides with amines. The best catalyst was identified as a Ni(II) complex of PVC-supported 2-[(2-aminoethylimino)methyl]phenol and it was used in the synthesis of a number of different β-amino alcohols. The catalyst was found to be reusable for up to five cycles.
Graphical abstract
Similar content being viewed by others
References
Kokotou VC (2002) Lett Pept Sci 9:143
Shanks RG, Wood TM, Dornhost AC, Clark ML (1966) Nature 212:88
De Cree J, Geukens H, Leempoels J, Verhaegen H (1986) Drug Dev Res 8:109
Ager DJ, Prakash I, Schaad DR (1996) Chem Rev 96:835
Bergmeier SC (2000) Tetrahedron 56:2561
Fache F, Schulz E, Tommasino ML, Lemaire M (2000) Chem Rev 100:2159
Kobayashi J, Ishibashi M (1996) Heterocycles 42:943
Lee HS, Kang SH (2004) Synlett 15:1673
Meyers AI (2005) J Org Chem 70:6137
Hodgson DM, Gibbs AR, Lee GP (1996) Tetrahedron 52:14361
Pasor IM, Yus M (2005) Curr Org Chem 9:1
Fan RH, Hou XL (2003) J Org Chem 68:726
Azoulay S, Manabe K, Kobayashi S (2005) Org Lett 7:4593
Kleiner CM, Schreiner PR (2006) Chem Commun 4315
Shivani, Pujala B, Chakraborti AK (2007) J Org Chem 72:3713
Bhanushali MJ, Nandurkar NS, Bhor MD, Bhanage BM (2008) Tetrahedron Lett 49:3672
Reddy BM, Patil MK, Reddy BT, Park SE (2008) Catal Commun 9:950
Tabatabaeian K, Mamaghani M, Mahmoodi NO, Khorshidi A (2008) Tetrahedron Lett 49:1450
Bao W, Liu Y, Lv X, Qian W (2008) Org Lett 10:3899
Zhang C, Chen J, Yu X, Chen X, Wu H, Yu J (2008) Synth Commun 38:1875
Kureshy RI, Prathap KJ, Agrawal S, Khan NH, Abdi SHR, Jasra RV (2008) Eur J Org Chem 3118
Procopio A, Gaspari M, Nardi M, Oliverio M, Rosati O (2008) Tetrahedron Lett 49:2289
Ollevier T, Nadeau E (2008) Tetrahedron Lett 49:1546
Sarvari MH (2008) Can J Chem 86:65
Krishnan GR, Sreekumar K (2008) Polymer 49:5233
Frenzel T, Solodenko W, Kirschning A (2003) In: Buchmeiser MR (ed) Polymeric materials in organic synthesis and catalysis. Wiley-VCH, Weinheim, pp 201–240
Leadbeater NE, Marco M (2002) Chem Rev 102:3217
McNamara CA, Dixon MJ, Bradley M (2002) Chem Rev 102:3275
Bergbreiter DE (2002) Chem Rev 102:3345
Bergbreiter DE, Tian J, Hongfa C (2009) Chem Rev 109:530
Ghosh P (2001) Polymer science and technology of plastics and rubbers. Tata McGraw-Hill, New Delhi, p 267
Andrady AL (1999) Polymer data handbook. Oxford University Press, New York
Blass CR (2001) The role of poly(vinyl chloride) in healthcare. Rapra Technology, Shawbury
Dong F, Li YQ, Dai RF (2007) Chin Chem Lett 18:266
Wei R, Liang Y, Chen S, Jia C, Li F, Zhang T (2002) J Appl Poly Sci 84:1067
Gil-Llambías FJ, Gargallo L, Radic D, Román E (1983) J Poly Sci Poly Lett Ed 21:897
Balakrishnan B, Jayakrishnan A (2005) Trends Biomater Artif Organs 18:230
Krishnan GR, Sreekumar K (2008) Eur J Org Chem 4763
Chu Z, Ding LQ, Long Y, Chen LL, Lu XQ, Song JR, Fan DD, Bao F, Ma R (2010) J Inorg Organomet Polym 20:235
Karmakar R, Choudhary CR, Mitra S, Dahlenburg L (2005) Struct Chem 16:611
Yoshida N, Oshio H, Ito T (1998) Chem Commun 63
de Castro B, Ferreira R, Freire C, Garcia H, Palomares EJ, Sabater MJ (2002) New J Chem 26:405
Acknowledgments
The authors would like to acknowledge Defense Research and Development Organization, India for financial support and the NMR research centre at the Indian Institute of Science, Bangalore for NMR spectral analysis.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Krishnan, G.R., Kajal, K.S. & Sreekumar, K. Synthesis of β-amino alcohols catalyzed by poly(vinyl chloride)-supported Schiff base metal complexes. Monatsh Chem 143, 637–642 (2012). https://doi.org/10.1007/s00706-011-0628-x
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00706-011-0628-x