Arylamino-thieno-oxobutanamides under Lawesson’s Conditions: Competition between Thienylpyrrole and Bithiophene Formation

Abstract

1-Aryl-2-thienyl-substituted pyrroles and/or 5-arylamino-2,2′-bithiophenes were synthesized by treatment of arylamino-thieno-oxobutanamides with Lawesson’s reagent. These in turn were prepared by direct amidation of 4-oxo-(2-thienyl)butanoic acid through DCC-BtOH mediated reactions.

Keywords

amides - substituent effects - pyrroles - bicyclic compounds - heterocycles

References

• 1 Sunderberg RJ. Pyrroles and their Benzo Derivatives: Synthesis and Applications, In Comprehensive Heterocyclic Chemistry   Vol. 4:  Katritzky AR. Rees CW. Pergamond; New York: 1984.  p.313 
• 2 Bohlmann F. Zdero C. In The Chemistry of Heterocyclic Compounds, Thiophene and Its Derivatives   Vol. 44:  Gronowitz S. Wiley; New York: 1985.  p.261 
• 3a Zyss DS. In Non-Linear Optical Properties of Organic Molecules and Crystals   Vol. 1:  Academic Press; Orlando: 1987. 
• 3b Zyss DS. In Non-Linear Optical Properties of Organic Molecules and Crystals   Vol. 2:  Academic Press; Orlando: 1987. 
• 4 Brosshard C. Sutter K. Petre P. Hulliger J. Florsheimer M. Kaatz M. Gunter P. In Organic Non-Linear Optical Materials   Gordon and Breach Science Publishers; Amsterdam: 1995. 
• 5 Lehn J.-M. In The Supramolecular Chemistry, Concepts and Perspectives   Gronowitz S. Wiley-VCH; Weinheim: 1995. 
• 6 Katritzky AR. Li J. Gordeev MF. Synthesis  1994,  93 
• 7 Engel N. Steglich W. Angew. Chem., Int. Ed. Engl.  1978,  17:  676 
• 8 Roncali J. Chem. Rev.  1992,  92:  711 
• 9 Roncali J. Chem. Rev.  1997,  97:  173 
• 10 Lucchesini F. Tetrahedron  1992,  48:  9951 
• 11 Ogura K. Yanay H. Miokawa M. Akazome M. Tetrahedron Lett.  1999,  40:  8887 
• 12 Zhao R. Akazome M. Matsumoto S. Ogura K. Tetrahedron  2002,  58:  10225 
• 13 Zhao R. Matsumoto S. Akazome M. Ogura K. Tetrahedron  2002,  58:  10233 
• 14 Ogura K. Zhao R. Yanay H. Maeda K. Tozawa R. Matsumoto S. Akazome M. Bull. Chem. Soc. Jpn.  2002,  75:  2359 
• 15 Ogura K. Zhao R. Jiang M. Akazome M. Matsumoto S. Yamaguchi K. Tetrahedron Lett.  2003,  44:  3595 
• 16 Just PE. Chane-Ching KI. Lacaze PC. Tetrahedron  2002,  58:  3467 
• 17 Kotkar D. Joshi V. Ghosh PK. J. Chem. Soc., Chem. Commun.  1988,  917 
• 18 Parakka JP. Joshi Cava MC. Synth. Met.  1995,  68:  275 
• 19 McCullough RD. Lowe RD. Jayaraman M. Anderson D. J. Org. Chem.  1993,  58:  904 
• 20 Shridhar DR. Jogibhukta M. Rao PS. Handa K. Synth. Commun.  1982,  1061 
• 21 Thomsen I. Pedersen U. Rasmussen PB. Yde B. Andersen TP. Lawesson S.-O. Chem. Lett.  1983,  809 
• 22 Cherkasov RA. Kutyrev GA. Pudovik AN. Tetrahedron  1985,  41:  2567 
• 23 Cava MP. Levinson I. Tetrahedron  1985,  41:  5061 
• 24 Bäuerle P. The Synthesis of Oligothiophenes, In Handbook of Oligo- and Polythiophenes   Fichou D. Wiley-VCH; Weinheim: 1999.  p.89-173  
• 25 Scheibye S. Pedersen BS. Lawesson S.-O. Bull. Soc. Chim. Belg.  1978,  87:  229 
• 26 Bean GP. In Pyrroles, The Chemistry of Heterocyclic Compounds   Vol. 48, Part 1:  Jones RA. Wiley; New York: 1990.  p.105 
• 27 Raposo MMM. Kirsch G. Heterocycles  2001,  55:  1487 
• 28 Raposo MMM. Kirsch G. Tetrahedron  2003,  59:  4891 
• 29 Raposo MMM. Fonseca AMC. Kirsch G. Tetrahedron  2004,  60:  4071 
• 30 Batista RMF. Costa SPG. Raposo MMM. Tetrahedron Lett.  2004,  45:  2825 
• 31 Fabrichnyi BP. Shalavina IF. Gol’dfarb YL. Zh. Obshch. Khim.  1958,  28:  213 ; Chem. Abstr.; 1959, 53: 3052f
• 32 Fieser L. Kennelly RG. J. Am. Chem. Soc.  1935,  57:  1611 
• 33 Nischo T. Helv. Chim. Acta  1998,  81:  1207