The intramolecular 1,3-dipolar cycloaddition of nitrilimines 3 allowed the obtainment of 4H-pyrazolo[5,1-c][1,4]benzothiazine S-oxides 4 and 5.
References
1.
PadwaA., in 1,3-Dipolar Cycloaddition Chemistry, ed. PadwaA., Wiley, New York, 1984, vol. 2, chap. 12.
2.
PadwaA., and SchoffstahlA. M. in Advances in Cycloaddition, ed. CurranD.P., YAI Press, London, 1990, vol. 2, p. 1.
3.
BrogginiG., MolteniG., and ZecchiG., Heterocycles, 1998, 47, 541.
4.
BruchéL., GarantiL., and ZecchiG., J. Chem. Soc., Perkin Trans. 1, 1981, 2245; L. Bruché, L. Garanti and G. Zecchi, J. Chem. Soc., Perkin Trans. 1, 1984, 2535.
5.
BruchéL., GarantiL., and ZecchiG., J. Chem. Res., 1986, (S) 210, (M) 1890; L. Bruché and G. Zecchi, J. Chem. Soc., Perkin Trans. 1, 1987, 399.
6.
StirlingC.J. M. in Organic Chemistry of Sulfur, ed. OaeS., Plenum Press, New York, 1977, ch. 9, p. 519.
7.
PosnerG.H. in Asymmetric Synthesis, ed. MorrisonJ.D., Academic Press, New York, 1983, p. 225; G.H. Posner, in The Chemistry of Sulphoxides and Sulphones, eds. S. Patai, Z. Rappoport and C.J.M. Stirling, Wiley, New York, 1988, ch. 16; G.H. Posner, Acc. Chem. Res., 1987, 20, 72 and references therein; A.J. Walker, Tetrahedron: Asymmetry, 1992, 3, 961; A.D. Westwell, M. Thornton-Pett and C.M. Rayner, J. Chem. Soc., Perkin Trans. 1, 1995, 847 and references therein; M.C. Carreño, Chem. Rev., 1995, 95, 1717; G.D. Solladié, in Houben-Weyl, Methods of Organic Chemistry, Stereoselective Synthesis, eds. G. Helmchen, R.W. Hoffmann, J. Mulzer and E. Schaumann, 1996, vol. E 21, p. 1056 and p. 1793.
8.
CarreteroJ.L., Garcia RuanoJ. L., LorenteA., and JusteF., Tetrahedron: Asymmetry, 1993, 4, 177 and references therein; M.A. Brimble, L.J. Duncalf and D.C.W. Reid, Tetrahedron: Asymmetry, 1995, 6, 263.
9.
KoizumiT., HiraiH., and YoshiiE., J. Org. Chem., 1982, 47, 4004; T. Takahashi, A. Fujii, J. Sugita, T. Hagi, K. Kitano, Y. Arai, T. Koizumi and M. Shiro, Tetrahedron: Asymmetry, 1991, 2, 1379; C. Louis and C. Hootelé, Tetrahedron: Asymmetry, 1995, 9, 2149.
10.
BravoP., BruchéL., FarinaA., FronzaG., MeilleS. V., and MerliA., Tetrahedron: Asymmetry, 1993, 4, 2131; P. Bravo, L. Bruché, G. Fronza and A. Merli, Gazz. Chim. Ital., 1994, 124, 275; P. Bravo, L. Bruché, M. Crucianelli, A. Farina, S.V. Meille, A. Merli and P. Seresini, J. Chem. Res., 1996, (S) 348, (M) 1901; P. Bravo, L. Bruché, P. Seresini and M. Zanda, J. Heterocycl. Chem., 1997, 34, 489. A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi, A. G. G. Moliterni, M. C. Burla, G. Polidori, M. Camalli, R. Spagna, SIR97, Program for Crystal Structure Solution, Università di Bari. G. M. Sheldrick, SHELXL-97, Program for Crystal Structure Refinement, Universität Göttingen, 1997.