Thermal, acid-catalyzed, and photolytic transformations of spirocyclic 3H-pyrazoles formed by reactions of methyl, phenyl, and p-tolyl phenylethynyl sulfones with 9-diazofluorene
Tóm tắt
Methyl, phenyl, and p-tolyl phenylethynyl sulfones react with 9-diazofluorene in diethyl ether at 20°C to give 1,3-dipolar cycloaddition products according to von Auwers’ rule, the corresponding spirocyclic 3H-pyrazoles. The spiro adducts undergo isomerization into 5-R-sulfonyl-3-phenylpyrazolo[1,5-f]phenanthridines on heating in boiling toluene for 2 h; heating of the same pyrazoles in boiling benzene, acetonitrile, or ethanol leads to mixtures of 5-R-sulfonyl-3-phenylpyrazolo[1,5-f]phenanthridines and 3-R-sulfonyl-3a-phenyl-3aH-dibenzo[e,g]indazoles, the latter prevailing. The indazoles are kinetically controlled thermolysis products which are quantitatively converted into phenanthridines on heating in toluene. Sulfonyl-substituted spirocyclic 3H-pyrazoles and indazoles in glacial acetic acid at 20°C in the presence of a catalytic amount of sulfuric acid are transformed into 3a-phenyl-2H-dibenzo[e,g]indazol-3(3aH)-one. Under analogous conditions, sulfonyl-substituted phenanhtridines give rise to 3-phenyl-1H-dibenzo[e,g]indazole. Photolysis of spirocyclic 3H-pyrazoles yields mixtures of sulfonylcyclopropenes and 2H-cyclopenta[j,k]fluorenes.
Tài liệu tham khảo
Bastide, J. and Ytnri-Rousstau, O., The Chemistry of the Carbon-Carbon Triple Bond, Patai, S., Ed., Chichester: Wiley, 1978, part 1, chap. 11, p. 448.
Regitz, M. and Heydt, H., 1,3-Dipolar Cycloaddition Chemistry, Padwa, A., Ed., New York: Wiley, 1984, vol. 1, chap. 4, p. 394.
Sammes, M.P. and Katritzky, A.R., Adv. Heterocycl. Chem., 1983, vol. 34, p. 1.
Maas, G., Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry toward Heterocycles and Natural Products, Padwa, A. and Pearson, W.H., Eds., New York: Wiley, 2002, chap. 8, p. 539.
Van Alphen, J., Recl. Trav. Chim. Pays-Bas, 1943, vol. 62, p. 491.
Hüttel, R., Franke, K., Martin, H., and Riedl, J., Chem. Ber., 1960. vol. 93, p. 1433.
Sammes, M.P. and Katritzky, A.R., Adv. Heterocycl. Chem., 1983, vol. 34, p. 53.
Nagai, T. and Hamaguchi, M., Org. Prep. Proced. Int., 1993, vol. 25, p. 403.
Back, T.G., Tetrahedron, 2001, vol. 57, p. 5263.
Gao, D., Zhai, H., Parvez, M., and Back, T.G., J. Org. Chem., 2008, vol. 73, p. 8057.
Back, T.G., Clary, K.N., and Gao, D., Chem. Rev., 2010, vol. 110, p. 4498.
Guillerm, G., L’Honoré, A., Veniard, L., Pourcelot, G., and Benaim, J., Bull. Soc. Chim. Fr., 1973, p. 2739.
Padwa, A. and Wannamaker, M.W., Tetrahedron, 1990, vol. 46, p. 1145.
Franck-Neumann, M. and Lohmann, J.-J., Angew. Chem., Int. Ed. Engl., 1977, vol. 16, p. 323.
Padwa, A. and Wannamaker, M.W., Tetrahedron Lett., 1986, vol. 27, p. 2555.
Padwa, A., Wannamaker, M.W., and Dyszlewski, A.D., J. Org. Chem., 1987, vol. 52, p. 4760.
Padwa, A. and Wannamaker, M.W., Tetrahedron, 1991, vol. 47, p. 6139.
Benati, L., Calestani, G., Nanni, D., Spagnolo, P., and Volta, M., Tetrahedron, 1997, vol. 53, p. 9269.
Bourissou, D. and Bertrand, G., Tetrahedron Lett., 1999, vol. 40, p. 883.
Dürr, N. and Sergio, R., Chem. Ber., 1974, vol. 107, p. 2027.
Yen, Y., Chen, S.-F., Heng, Z.-C., Huang, J.-C., Kao, L.-C., Lai, C.-C., and Liu, R.S.H., Heterocycles, 2001, vol. 55, p. 1859.
Mataka, S. and Tashiro, M., J. Org. Chem., 1981, vol. 46, p. 1929.
Fedorov, A.A., Duisenbaev, Sh.E., Razin, V.V., Kuznetsov, M.A., and Linden, E., Russ. J. Org. Chem., 2007, vol. 43, p. 231.
Dürr, H. and Schrader, L., Z. Naturforsch., Teil B, 1969, vol. 24, p. 536.
Jones, G.W., Chang, K.T., and Shechter, H., J. Am. Chem. Soc., 1979, vol. 101, p. 3906.
Schiess, P. and Stalder, H., Tetrahedron Lett., 1980, vol. 21, p. 1413.
Reimlinger, H., Chem. Ber., 1967, vol. 100, p. 3097.
Silverstein, R.M., Webster, F.X., and Kiemle, D.J., Spectrometric Identification of Organic Compounds, Hoboken, NJ: Wiley, 2005, 7th ed.
Razin, V.V. and Gupalo, V.I., Zh. Org. Khim., 1974, vol. 10, p. 2342.
Baron, W.J., Hendrick, M.E., and Jones, M., J. Am. Chem. Soc., 1973, vol. 95, p. 6286.
Razin, V.V., Zh. Org. Khim., 1975, vol. 11, p. 1457.
Leach, J.C.L. and Wilson, J.W., J. Org. Chem., 1978, vol. 43, p. 4880.
Dürr, H. and Gleiter, R., Angew. Chem., 1978, vol. 90, p. 591.
Burgert, W., Groâe, M., and Rewicki, D., Chem. Ber., 1982, vol. 115, p. 309.
Ege, G., Tetrahedron Lett., 1963, vol. 4, p. 1667.
Dürr, H., Fröhlich, S., Schley, B., and Weisgerber, H., J. Chem. Soc., Chem. Commun., 1977, p. 843.
CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171.NET).
Sheldrick, G.M., SHELXL97, SHELXS97, Göttingen, Germany: Univ. of Göttingen, 1997.
Farrugia, L.J., J. Appl. Crystallogr., 1999, vol. 32, p. 837.
Truce, W.E. and Wolf, G.C., J. Org. Chem., 1971, vol. 36, p. 1727.
Amiel, Y., J. Org. Chem., 1974, vol. 39, p. 3867.
Friedrichsen, W., Schwarz, I., Epe, B., and Hesse, K.-F., Z. Naturforsch., Teil B, 1981, vol. 36, p. 622.