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Synthesis of Naphtho[2,1]-b]furanylium Cation and Its Reaction with Alcohols and Trialkyl Phosphites

Identyfikatory
Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
The reaction between dibenzoylacetylene and 2-naphthol in the presence of a catalytic amount of pyridine leads to 2-hydroxy-1-(2-oxo-2-phenylethylidene)-2-phenyl-1,2- dihydro-naphtho[2,1-b]furan in nearly quantitative yield. Treatment of this heterocyclic system with trimethyl chlorosilane in chloroform leads quantitatively to 1-(2-oxo-2- phenylethylidene)-2-phenyl-1H-naphtho[2,1-b]furanylium chloride. Addition of nucleophiles such as alcohols or trialkyl phosphites to this salt produces functionalized 1,2- dihydronaphthofuran derivatives in excellent yields.
Rocznik
Strony
361--367
Opis fizyczny
Bibliogr. 10 poz., rys.
Twórcy
autor
  • Department of Chemistry, University of Tarbiat Modarres, PO Box 14115-175, Tehran, Iran
  • Department of Chemistry, University of Tarbiat Modarres, PO Box 14115-175, Tehran, Iran
autor
  • Department of Chemistry, University of Tarbiat Modarres, PO Box 14115-175, Tehran, Iran
Bibliografia
  • 1.Lindell S.D., in Comprehensive Organic Functional Group Transformations, Elsevier Science Ltd. Pergamon, 1st edn. p. 1007 (1995).
  • 2.1. (a) Olah G.A. and Calin A., J. Am. Chem Soc., 90, 938 (1968); (b) Childs R.F., Faggiani R., Lock C.J.L., Mahendran M. and Zweep S.D., J. Am. Chem. Soc., 108, 1692 (1986).
  • 3.(a) Mir-Mohamad-Sadeghy M. and Rickbom B., J. Org. Chem., 48, 2237 (1983); (b) Cornejo J.J., Ghodsi S., Johnson RD., WoodlingR. and Rickbom B.,J Org. Chem., 48,3869 (1983); (c) OhmuraH. and Mikami K., Tetrahedron Lett., 42, 6859 (2001).
  • 4. Olah G.A. and Svoboda J.J., Synthesis, 306 (1972).
  • 5. (a) Joule J.A., Mills K. and Smith G.F., Heterocyclic Chemistry, Chapman & Hall, London 3rd edn, pp. 146-183 (1995); (b)FichtnerC., Remennikov G. and Mayr H, Eur. J Org. Chem., 4451 (2001);(c)Lu Y. and Foo L., Tetrahedron Lett., 43, 715 (2002).
  • 6. Basavaiah D., Sreenivasulu B. and Rao J.S., Tetrahedron Lett., 42, 1147 (2001).
  • 7. Yavari I., Anary-Abbasinejad M. and Alizadeh A., Tetrahedron Lett., 43, 4503 (2002).
  • 8. Tcbby J.C., Verkede J.G. and Quin L.D., Phosphorus-31 NMR Spectroscopy in Stereochemical Analysis, VCH Publishers: Weinheim; ch. 1, p. 34 (1987).
  • 9. Skattebol L., Jones E.R.H. and Whiting M.C., Org. Synth. Coll. Vol., 4, 792 (1963).
  • 10. Bowden K., Heilbron I.M., Jones E.R.H. and Weedon B.C., J. Chem. Soc., 39 (1946).
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-article-BUJ1-0023-0181
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