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Synthesis 2012; 44(13): 1993-1996
DOI: 10.1055/s-0031-1291123
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Cyanoacetyl Oxazolidinones

Kaitlyn M. Weeber
Genentech, Inc., 1 DNA Way, S. San Francisco, CA 94080, USA, Fax: +1(650)7424943   Email: schwarz.jacob@gene.com
,
Jacob B. Schwarz*
Genentech, Inc., 1 DNA Way, S. San Francisco, CA 94080, USA, Fax: +1(650)7424943   Email: schwarz.jacob@gene.com
› Author Affiliations
Further Information

Publication History

Received: 22 March 2012

Accepted after revision: 16 April 2012

Publication Date:
25 May 2012 (online)

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Abstract

Carefully controlled displacement of chiral chloroacetyl imides with cyanide afforded previously unreported cyanoacetimides in good overall yield. Knoevenagel condensation of the cyanoacetimides to furnish acrylonitriles was also demonstrated.

Key words

oxazolidinone - Knoevenagel - cyanoacetic - chloroacetic - tetrabutylammonium cyanide

Supporting Information

    for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis. Included are copies of 1H and 13C NMR spectra of compounds 1a, 1b, 1c, 1d, 2a, 2b, and 4a.
  • Supporting Information
 

  • References

  • 1 Thorsen TS, Madsen KL, Rebola N, Rathje M, Anggono V, Bach A, Moreira IS, Stuhr-Hansen N, Dyhring T, Peters D, Beuming T, Huganir R, Weinstein H, Mulle C, Stromgaard K, Ronn LC. B, Gether U. Proc. Natl. Acad. Sci. U.S.A. 2010; 107: 413
    CrossrefSearch in Google Scholar
  • 2 Bach A, Stuhr-Hansen N, Thorsen TS, Bork N, Moreira IS, Frydenvang K, Padrah S, Christensen SB, Madsen KL, Weinstein H, Gether U, Strømgaard K. Org. Biomol. Chem. 2010; 8: 4281
    CrossrefSearch in Google Scholar
  • 3 Lin J, Huang C, Yan S, Ni Y, Huang R, Chen B. Chinese Patent CN 2008-10233712, 2, 2008 ; Chem. Abstr. 2009, 151, 148317 (Patent written in Chinese). No experimentals for preparing compounds of type 2 were provided
  • 4 Schwarz JB, Gibbons SE, Graham SR, Colbry NL, Guzzo PR, Le V.-D, Vartanian MG, Kinsora JJ, Lotarski SM, Li Z, Dickerson MR, Su T.-Z, Weber ML, El-Kattan A, Thorpe AJ, Donevan SD, Taylor CP, Wustrow DJ. J. Med. Chem. 2005; 48: 3026
    CrossrefSearch in Google Scholar
  • 5 Patel N, Schwarz JB, Islam K, Miller W, Tran TP, Wei Y. Synth. Commun. 2011; 41: 2209
    CrossrefSearch in Google Scholar
  • 6 Although Scifinder shows that 1b was previously reported, it was actually the isocyanide: Tang JS, Verkade JG. J. Org. Chem. 1996; 61: 8750
    CrossrefSearch in Google Scholar
  • 7 SmI2-promoted rearrangement of isocyanides of the type reported in ref. 3 to nitriles similar to 1 have been reported: Kang H.-Y, Pae AN, Cho YS, Koh HY, Chung BY. Chem. Commun. 1997; 821
  • 8 Evans DA, Ennis MD, Mathre DJ. J. Am. Chem. Soc. 1982; 104: 1737
    CrossrefSearch in Google Scholar
  • 9 Evans DA, Weber AE. J. Am. Chem. Soc. 1986; 108: 6757
    CrossrefSearch in Google Scholar
  • 10 Katz HE, Schilling ML. J. Org. Chem. 1989; 111: 7554
    Search in Google Scholar
  • 11 In entry 8, a modified chromatography eluent system (EtOAc–CH2Cl2) was utilized owing to reduced solubility of product 1d, see the experimental section
  • 12 Abu-Bakr SM, El-Shehry MF, El-Telbani EM, Nawwar GA. M. Pharm. Chem. J. 2010; 44: 433
    CrossrefSearch in Google Scholar
  • 13 Abdel-Magid A, Lantos I, Pridgen LN. Tetrahedron Lett. 1984; 25: 3273
    CrossrefSearch in Google Scholar
  • 14 Evans DA, Sjogren EB, Weber AE, Conn RE. Tetrahedron Lett. 1987; 28: 39
    CrossrefSearch in Google Scholar
  • 15 Feroci M, Inesi A, Palombi L, Sotgiu G. J. Org. Chem. 2002; 67: 1719
    CrossrefSearch in Google Scholar