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Synthesis 2008(11): 1679-1681
DOI: 10.1055/s-2008-1067040
DOI: 10.1055/s-2008-1067040
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York
Rapid and Convenient Microwave-Assisted Synthesis of Primary Amines via Reductive N-Alkylation of Methyl Carbamate with Aldehydes
Further Information
Received
20 February 2008
Publication Date:
29 April 2008 (online)
Publication History
Publication Date:
29 April 2008 (online)
Abstract
Microwave-assisted reductive alkylation of methyl carbamate with a range of aldehydes provides, after basic work-up, an experimentally simple, one-pot method for rapid functional group interconversion of structurally diverse aldehydes into primary amines. The method has several advantages over more traditional methods of carrying out this transformation and is particularly amenable to high-throughput synthesis.
Key words
aminations - aldehydes - reductive alkylation - carbamates - amines - microwave synthesis
-
1a
March J.Smith MB. In Advanced Organic Chemistry 5th ed.:Smith MB. Wiley; New York: 2001. p.1187 -
1b
Please G.Thoralf S.Abdul M.Ahmad M.Beller M. Org. Lett. 2002, 4: 2055 -
2a
Warshawsky AM.Alt CA.Brozinick JT.Harkness AR.Hawkins ED.Henry JR.Matthews DP.Miller AR.Misener EA.Montrose-Rafizadeh C.Rhodes GA.Shen Q.Vance JA.Udodong UE.Wang M.Zhang TY.Zink RW. Bioorg. Med. Chem. Lett. 2006, 16: 6328 -
2b
Bennasar ML.Roca T.Monerris M.Garcia-Diaz D. J. Org. Chem. 2006, 71: 7028 -
2c
Simunek P.Peskova M.Bertolasi V.Machacek V.Lycka A. Tetrahedron 2005, 61: 8130 -
3a
Jones GH.Venuti MC.Alvarez R.Bruno JJ.Berks AH.Prince A. J. Med. Chem. 1987, 30: 295 -
3b
Gilbert AM.Antane MM.Argentieri TM.Butera JA.Francisco GD.Freeden C.Gundersen EG.Graceffa RF.Herbst D.Hirth BH.Lennox JR.McFarlane G.Norton NW.Quagliato D.Sheldon JH.Warga D.Wojdan A.Woods M. J. Med. Chem. 2000, 43: 1203 - 4
Maslak V.Yan Z.Xia S.Gallucci J.Hadad CM.Badjic JD. J. Am. Chem. Soc. 2006, 128: 5887 - 5
Dube D.Scholte AA. Tetrahedron Lett. 1999, 40: 2295 - 6
Hamada Y,Umezu K, andYoshida Y. inventors; PCT Int. Appl. WO 2002096853. ; Chem. Abstr. 2003, 138, 4423 -
7a
Grant EB.Guiadeen D.Abbanat D.Foleno BD.Bush K.Macielag MJ. Bioorg. Med. Chem. Lett. 2006, 16: 1929 -
7b
Zhu B.Maden A.Macielag MJ. Tetrahedron Lett. 2005, 46: 1783 -
7c
Henninger TC.Xu X.Abbanat D.Baum EZ.Foleno BD.Hilliard JJ.Bush K.Hlasta DJ.Macielag MJ. Bioorg. Med. Chem. Lett. 2004, 14: 4495