A New Entry to Functionalized 4-Aryl-2-methylenetetralones

Abstract

A new SnCl₄-induced rearrangement of 2,5-diaryl-2,3-dihydrofurans allows a direct and efficient formation of the 4-aryl-2-methylenetetralone skeleton. Its scope and limitations are discussed.

Key words

2,3-dihydrofurans - methylenetetralones - rearrangements - Lewis acids - ring-opening

References

• 1a Cassady JM. Byrn SR. Stamos IK. Evans SM. McKenzie A. J. Med. Chem.  1978,  21:  815 
• 1b Paquette LA. Méndez-Andino J. Tetrahedron Lett.  2002,  40:  4301 
• 1c Lee K.-H. Huang B.-R. Tzeng C.-C. Bioorg. Med. Chem. Lett.  1999,  9:  241 
• 2 Kupchan SM. Fessler DC. Eakin MA. Giacobbe TJ. Science  1970,  168:  376 
• 3 Bentley PA. Bickley JF. Roberts M. Steiner A. Tetrahedron Lett.  2001,  42:  3741 
• 4a López-Pérez JL. del Olmo E. de Pascual-Teresa B. Merino M. San Feliciano A. Tetrahedron  1996,  52:  4903 
• 4b Madrigal B. Puebla P. Ramos A. Peláez R. Grávalos D. Caballero E. Medarde M. Bioorg. Med. Chem.  2002,  10:  303 
• 5 Yang FZ. Trost MK. Fristad WE. Tetrahedron Lett.  1987,  28:  1493 
• 6 Garzino F. Méou A. Brun P. Tetrahedron Lett.  2002,  43:  5049 
• 7 Garzino F. Méou A. Brun P. Tetrahedron Lett.  2000,  41:  9803 
• 9 Murphy WS. Wattanasin S. J. Chem. Soc., Perkin Trans. 1  1982,  271 
• Stevenson and co-workers have described the synthesis of 4-aryltetralins by cyclization of β-benzyl-α-(hydroxybenzyl)-butyrolactones with TFA:
• 10a Ganeshpure PA. Stevenson R. J. Chem. Soc., Perkin Trans. 1  1981,  1681 
• 10b Ganeshpure PA. Schneiders GE. Stevenson R. Tetrahedron Lett.  1981,  22:  393 

8

Compound 6 could be stored for few hours in pyridine at -15 °C.