Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2011(3): 485-489
DOI: 10.1055/s-0030-1258366
DOI: 10.1055/s-0030-1258366
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Glycerine and CeCl3˙7H2O: An Efficient and Recyclable Reaction Medium for Ring Opening of Epoxides with Thioamides and Amines
Further Information
Received
22 October 2010
Publication Date:
14 December 2010 (online)
Publication History
Publication Date:
14 December 2010 (online)
Abstract
Oxiranes undergo rapid ring-opening reaction with a range of thioamides and amines to afford the corresponding β-amino alcohol derivatives. The reactions were carried out using glycerine and cerium(III) chloride as a recyclable reaction medium. All the reactions were carried out at room temperature and the products were obtained in excellent yields.
Key words
epoxides - amines - thioamides - amino alcohols - glycerine - cerium chloride.
-
1a
Rao AS. Comprehensive Organic Synthesis Vol. 7:Trost BM.Fleming I. Pergamon Press; Oxford: 1991. p.357-387 -
1b
Corey EJ.Zhang F. Angew. Chem. Int. Ed. 1999, 38: 1931 -
1c
O’Brien P. Angew. Chem. Int. Ed. 1999, 38: 326 -
1d
Ager DJ.Prakash I.Schaad DR. Chem. Rev. 1996, 96: 835 -
1e
De Cree J.Geukens H.Leempoels J.Verhaegen H. Drug Dev. Res. 1986, 8: 109 -
2a
Connolly ME.Kersting F.Bollery CT. Prog. Cardio. Dis. 1976, 19: 203 -
2b
Bose DS.Narsaiah AV. Bioorg. Med. Chem. 2005, 3: 627 -
2c
Erhardt PW.Woo CW.Anderson WG.Gorczynski AR. J. Med. Chem. 1982, 25: 1408 -
2d
Zhu S.Meng L.Zhang Q.Wei L. Bioorg. Med. Chem. Lett. 2006, 16: 1854 -
3a
Hodgson DM.Gibbs AR.Lee GP. Tetrahedron 1996, 52: 14361 -
3b
Bergmeier SC. Tetrahedron 2000, 56: 2561 -
3c
Hanson RM. Chem. Rev. 1991, 91: 437 -
3d
Deyrup JA.Moyer CL. J. Org. Chem. 1969, 34: 175 -
4a
Ollevier T.Compin GL. Tetrahedron Lett. 2002, 43: 7891 -
4b
Iqbal J.Pandey A. Tetrahedron Lett. 1990, 31: 575 -
4c
Pachon LD.Gamez JJM.Reedijik VB. Tetrahedron Lett. 2003, 44: 6025 -
4d
Chakraborti AK.Kondaskar A. Tetrahedron Lett. 2003, 44: 8315 - 5
Chini M.Crotti P.Macchia F. J. Org. Chem. 1991, 56: 5939 -
6a
Auge J.Leroy F. Tetrahedron Lett. 1996, 37: 7715 -
6b
Sekhar G.Singh VK. J. Org. Chem. 1999, 64: 287 -
6c
Meguro N.Asao N.Yamamoto Y. J. Chem. Soc., Perkin Trans. 1 1994, 2597 -
6d
Cepanec I.Latvic M.Mikuldas H.Bartolincic A.Vinkovic V. Tetrahedron 2003, 59: 2435 -
6e
Fujiwara M.Imada M.Baba A.Matsuda H. Tetrahedron Lett. 1989, 30: 739 -
6f
Yadav JS.Reddy BVS.Basak AK.Narsaiah AV. Tetrahedron Lett. 2003, 44: 1047 -
7a
Gu Y.Jerome F. Green Chem. 2010, 12: 1127 -
7b
Wolfson A.Dlugy C.Shotland Y.Tavor D. Tetrahedron Lett. 2009, 50: 5951 -
7c
Garcia J.Marin HG.Mayoral JA.Perez P. Green Chem. 2010, 12: 426 -
7d
Gu Y.Barrault J.Jerome F. Adv. Synth. Catal. 2008, 350: 2007 -
7e
Wolfson A.Dlugy C.Shotland Y. Environ. Chem. Lett. 2007, 5: 67 -
7f
Wolfson A.Dlugy C.Shotland Y.Tavor D. Tetrahedron Lett. 2009, 50: 5951 -
8a
Silveira CC.Mendes SR.Libero FM.Lenardo EJ.Perin G. Tetrahedron Lett. 2009, 50: 6060 -
8b
Narsaiah AV.Nagaiah B. Asian J. Chem. 2010, 22: 8099 -
8c
Narsaiah, A. V.; Kumar, J. K. Synth. Commun. 2010, submitted for publication.