Synthesis of Cyanoacetyl Oxazolidinones

Kaitlyn M. Weeber; Jacob B. Schwarz

doi:10.1055/s-0031-1291123

Synthesis, Table of Contents

Synthesis 2012; 44(13): 1993-1996
DOI: 10.1055/s-0031-1291123

paper

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

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Abstract

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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

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References

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
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
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
5 Patel N, Schwarz JB, Islam K, Miller W, Tran TP, Wei Y. Synth. Commun. 2011; 41: 2209
6 Although Scifinder shows that 1b was previously reported, it was actually the isocyanide: Tang JS, Verkade JG. J. Org. Chem. 1996; 61: 8750
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
9 Evans DA, Weber AE. J. Am. Chem. Soc. 1986; 108: 6757
10 Katz HE, Schilling ML. J. Org. Chem. 1989; 111: 7554
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
13 Abdel-Magid A, Lantos I, Pridgen LN. Tetrahedron Lett. 1984; 25: 3273
14 Evans DA, Sjogren EB, Weber AE, Conn RE. Tetrahedron Lett. 1987; 28: 39
15 Feroci M, Inesi A, Palombi L, Sotgiu G. J. Org. Chem. 2002; 67: 1719

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