Synthesis 2002(7): 0875-0878
DOI: 10.1055/s-2002-28523
PAPER
© Georg Thieme Verlag Stuttgart · New York

One-Step Synthesis of Thioaurones

M. Grazia Cabiddu, Salvatore Cabiddu*, Enzo Cadoni, Stefania De Montis, Claudia Fattuoni, Stefana Melis, Michele Usai
Dipartimento di Scienze Chimiche, Università degli Studi di Cagliari, Cittadella Universitaria di Monserrato, SS 554 Bivio per Sestu, 09042 Monserrato (CA), Italy
Fax: +39(70)6754388; e-Mail: scabiddu@unica.it;
Further Information

Publication History

Received 7 November 2001
Publication Date:
14 May 2002 (online)

Abstract

A rapid, one-step preparation of 2-(arylmethylidene)-1-benzothiophen-3-ones (thioaurones) using directed α-metallation, ring closure and aldol-type condensation is described. The reaction leads exclusively to the Z-isomer.

    References

  • 1 Ahlheim M. Barzoukas M. Bedworth PV. Blanchard-Desce M. Fort A. Hu ZY. Marder SR. Perry JW. Runser C. Staehelin M. Zysset B. Science (Washington, D.C.)  1996,  271:  335 
  • 2 Auwers K. Arndt F. Chem. Ber.  1909,  42:  537 
  • 3 Rajappa S. Comprehensive Heterocyclic Chemistry   Vol 4:  Katritzky AR. Rees CW. Pergamon; Oxford: 1984.  p.822 
  • 4 Hofmann H. Westernacher H. Haberstrah HJ. Chem. Ber.  1973,  106:  349 
  • 5 Taylor AW. Dean DK. Tetrahedron Lett.  1988,  29:  1845 
  • 6 Wadsworth DH. Detty MR. J. Org. Chem.  1980,  45:  4611 
  • 7 Gilman H. Haubein AH. J. Am. Chem. Soc.  1944,  66:  1515 
  • 8 Brandsma L. Preparative Polar Organometallic Chemistry   Vol 1:  Springer; Berlin: 1990.  p.19 
  • 9 Dickinson RP. Iddon B. J.Chem. Soc. (C)  1970,  1926 
  • 10 Mostoslavski MA. Izmailski VA. Zh. Obshch Khim.  1961,  31:  17 ; Chem. Abstr. 1961, 55, 26659g