New route to o-terphenyls: application to the synthesis of 6,7,10,11-tetramethoxy-2-(methoxycarbonyl)triphenylene

Abstract

The hydroxy-o-terphenylcarboxylic acid esters 6a–f have been prepared by benzannulation of the 5,6-diaryl-3-methoxycarbonylhexa-3,5-dienoic acids 5a–f using triethylamine–ethyl chloroformate. The application of this new synthesis of triphenylenes is illustrated through the synthesis of 2-methoxycarbonyl-6,7,10,11-tetramethoxytriphenylene 9.

References

1. N. Boden, R. J. Bushby and A. N. Cammidge, J. Am. Chem. Soc., 1995, 117, 924.
2. W. Kreuder and H. Ringsdorf, Makromol. Chem. Rapid Commun., 1983, 4, 807; W. Kreuder, H. Ringsdorf and P. Tschirner, Makromol. Chem. Rapid Commun., 1985, 6, 367.
3. I. M. Matheson, O. C. Musgrave and C. J. Webster, Chem. Commun., 1965, 278; N. Boden, R. C. Borner, R. J. Bushby, A. N. Cammidge and M. V. Jesudason, Liq. Cryst., 1993, 15, 851.
4. N. Boden, R. J. Bushby and A. N. Cammidge, J. Chem. Soc., Chem. Commun., 1994, 465.
5. R. C. Borner and R. F. W. Jackson, J. Chem. Soc., Chem. Commun., 1984, 845; G. Wenz, Makromol. Chem. Rapid Commun., 1985, 6, 577.
6. R. J. Bushby and C. Hardy, J. Chem. Soc., Perkin Trans. 1, 1986, 721.
7. G. W. Gray, M. Hird, D. Lacey and K. J. Toyne, J. Chem. Soc., Perkin Trans. 2, 1989, 2041; J. W. Goodby, M. Hird, K. J. Toyne and T. Watson, J. Chem. Soc., Chem. Commun., 1994, 1701.
8. E. Brenna, C. Fuganti, V. Perozzo and S. Serra, Tetrahedron, 1997, 53, 15 029.
9. K. Clinch, C. J. Marquez, M. J. Parrott and R. Ramage, Tetrahedron, 1989, 45, 239.
10. J. R. Johnson, Org. React., 1942, 1, 220.
11. K. Ishizumi, K. Koga and S. I. Yamada, Chem. Pharm. Bull., 1968, 16, 492.
12. W. S. Johnson and G. H. Daub, Org. React., 1951, 6, 2.
13. R. F. Hudson and P. A. Chopard, Helv. Chim. Acta, 1963, 46, 2179.
14. W. J. Musliner and J. W. Gates Jr., J. Am. Chem. Soc., 1966, 88, 4271.
15. P. Henderson, S. Kumar, J. A. Rego, H. Ringsdorf and P. Schumacher, J. Chem. Soc., Chem. Commun., 1995, 1059.