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Synthesis 1987; 1987(2): 149-153
DOI: 10.1055/s-1987-27866
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Synthesis of 2,2-Dimethyl-2H-thiochromenes, the Sulfur Analogs of Precocenes

J. Tércio* , B. Ferreira, V. Catani, J. V. Comasseto
  • *Departamento de Química - UFSCar, Cx. Postal 676 13560 - São Carlos - SP, Brazil
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Publication Date:
12 September 2002 (online)

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A new general synthesis of 2,2-dimethyl-2H-thiochromenes in good yield consists of the Michael addition of thiophenols to 3-methyl-2-butenoic acid, intramolecular cyclocondensation of the resultant 3-methyl-3-phenylthiobutanoic acids, reduction of the 2,2-dimethyl-4-oxothiochromenes thus obtained with sodium borohydride, and acid-catalyzed dehydration of the resultant 4-hydroxy-2,2-dimethylthiochromans.