Microwave-Assisted Synthesis of 5-Substituted 2-Aminothiophenes Starting from Arylacetaldehydes

Abstract

An easy three-step pathway for the synthesis of arylacet­aldehydes from the corresponding carboxylic acids in very high yields is described. Their use as precursors of 5-substituted-2-aminothiophenes is illustrated via a microwave-assisted Gewald reaction. This method allows obtaining the expected compounds in a shorter time and with better yields and purities than the classical procedures.

Key words

Gewald reaction - 5-substituted-2-aminothiophenes - microwave - arylacetaldehydes

References

• 1a Sabnis RW. Rangnekar DW. Sonawane ND. J. Heterocycl. Chem.  1999,  36:  333 
• 1b Puterová Z. Krutoíková A. Végh D. ARKIVOC  2010,  (i):  209 
• 2 Briel D. Rybak A. Kronbach C. Unverferth K. Eur. J. Med. Chem.  2010,  45:  69 
• 3 Bowers S. Truong AP. Neitz RJ. Neitzel M. Probst GD. Hom RK. Peterson B. Galemmo RA. Konradi AW. Sham HL. Tóth G. Pan H. Yao N. Artis DR. Brigham EF. Quinn KP. Sauer JM. Powell K. Ruslim L. Ren Z. Bioorg. Med. Chem. Lett.  2011,  21:  1838 
• 4 Ye P. Kuhn C. Juan M. Sharma R. Connolly B. Alton G. Liu H. Stanton R. Kablaoui NM. Bioorg. Med. Chem. Lett.  2011,  21:  849 
• 5 Thomae D. Perspicace E. Xu Z. Henryon D. Schneider S. Hesse S. Kirsch G. Seck P. Tetrahedron  2009,  65:  2982 
• 6 Thomae D. Kirsch G. Seck P. Synthesis  2007,  1027 
• 7 Abdillahi I. Kirsch G. Synthesis  2010,  1428 
• 8 Hesse S. Perspicace E. Kirsch G. Tetrahedron Lett.  2007,  48:  5261 
• 9 Gewald K. Schinke E. Böttcher H. Chem. Ber.  1966,  99:  94 
• 10 Chandrasekhar S. Kumar MS. Muralidhar B. Tetrahedron Lett.  1998,  39:  909 
• 11 Dickson HD. Smith SC. Hinkle KW. Tetrahedron Lett.  2004,  45:  5597 
• 12 Luzzio FA. Fitch RW. Moore WJ. Mudd KJ. J. Chem. Educ.  1999,  76:  974 
• 13 Fernandes RA. Kumar P. Tetrahedron Lett.  2003,  44:  1275 
• 14 Frigerio M. Santagostino M. Sputore S. Palmisano G. J. Org. Chem.  1995,  60:  7272 
• 15 Lin C.-K. Lu T.-J. Tetrahedron  2010,  66:  9688 
• 16 Wang K. Kim D. Dömling A. J. Comb. Chem.  2010,  12:  111 
• 17a Sridhar M. Rao RM. Baba NHK. Kumbhare RM. Tetrahedron Lett.  2007,  48:  3171 
• 17b Frutos Hoener AP. Henkel B. Gauvin JC. Synlett  2003,  63 
• 18a Huang W. Li J. Tang J. Liu H. Shen J. Jiang H. Synth. Commun.  2005,  35:  1351 
• 18b Treu M. Karner T. Kousek R. Berger H. Mayer M. McConnell DB. Stadler A. J. Comb. Chem.  2008,  10:  863 
• 19 Sibor J. Pazdera P. Molecules  1996,  157