Dipolar cycloadditions of mesoionic compounds with 2-tert-butylfulvenes. A new route to pseudo-hetero-azulenes via sterically assisted [4π + 6π] cycloadditions, and isomerization of adducts

Tetrahedron

Volumn 53, Issue 29, 1997, Pages 9921-9934

  Kato, Hiroshi ^a   Kobayashi, Tomoshige ^a   Ciobanu, Mona ^a   Kakehi, Akikazu ^a  

^a SHINSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMPHOLYTE; CYCLOPENTANE DERIVATIVE; FULVENE DERIVATIVE; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; ISOMERISM; MASS SPECTROMETRY; MOLECULAR DYNAMICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; THEORY; ULTRAVIOLET SPECTROPHOTOMETRY; X RAY ANALYSIS;

EID: 0342601498     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00337-2     Document Type: Article

References (45)

1. Heterocycles by cycloaddition. Part 13. Part 12: Kobayashi, T.; Minemura, H.; Kato, H. Heterocycles. 1995, 40, 311-317.
2. Partly reported in a preliminary form: Kato, H.; Kobayashi, T.; Ciobanu, M.; Iga, H.; Akutsu, A.; Kakehi, A. Chem. Commun., 1996, 1011-1012.
3. Review on cycloaddition reactions of mesoionic compounds: Potts, K. T. Mesoionic Ring Systems. In 1,3-Dipolar Cycloaddition Chemistry, Padwa, A. Ed.; Wiley, New York, Vol. 2, 1984, pp. 1-82
4. Reviews on mesoionic compounds including cycloaddition: Ohta, M.; Kato, H. Sydnones and Other Mesoionic Compounds. In Nonbenzenoid Aromatics, Snyder, J. P. Ed; Academic, New York, 1969, pp. 117-248; Ramsden, C. A. Meso-ionic Heterocycles. In Comprehensive Organic Chemistry, Barton, D. H. R., Ollis, W. D. Eds; Pergamon, Oxford, Vol. 4, 1979, pp. 1171-1228; Ollis, W. D.; Ramsden, C. A. Meso-ionic Heterocycles. In Adv. Heterocycl. Chem., Katritzky, A. R.; Boulton, A. J. Eds.; Academic, New York, Vol. 19, 1976, pp. 1- 122; Newton, C. G.; Ramsden, C. A. Tetrahedron, 1982, 38, 2965-3011; Ollis, W. D.; Stanforth, S. P. Tetrahedron, 1985, 41, 2239-2329; Gingrich, H. L., Baum, J. S. Mesoionic Oxazoles. In The Chemistry of Heterocyclic Compounds, Turchi, I. D. Ed. Wiley, New York, Vol. 45, 1986, pp. 731-961.
5. Reviews on mesoionic compounds including cycloaddition: Ohta, M.; Kato, H. Sydnones and Other Mesoionic Compounds. In Nonbenzenoid Aromatics, Snyder, J. P. Ed; Academic, New York, 1969, pp. 117-248; Ramsden, C. A. Meso-ionic Heterocycles. In Comprehensive Organic Chemistry, Barton, D. H. R., Ollis, W. D. Eds; Pergamon, Oxford, Vol. 4, 1979, pp. 1171-1228; Ollis, W. D.; Ramsden, C. A. Meso-ionic Heterocycles. In Adv. Heterocycl. Chem., Katritzky, A. R.; Boulton, A. J. Eds.; Academic, New York, Vol. 19, 1976, pp. 1- 122; Newton, C. G.; Ramsden, C. A. Tetrahedron, 1982, 38, 2965-3011; Ollis, W. D.; Stanforth, S. P. Tetrahedron, 1985, 41, 2239-2329; Gingrich, H. L., Baum, J. S. Mesoionic Oxazoles. In The Chemistry of Heterocyclic Compounds, Turchi, I. D. Ed. Wiley, New York, Vol. 45, 1986, pp. 731-961.
6. Reviews on mesoionic compounds including cycloaddition: Ohta, M.; Kato, H. Sydnones and Other Mesoionic Compounds. In Nonbenzenoid Aromatics, Snyder, J. P. Ed; Academic, New York, 1969, pp. 117-248; Ramsden, C. A. Meso-ionic Heterocycles. In Comprehensive Organic Chemistry, Barton, D. H. R., Ollis, W. D. Eds; Pergamon, Oxford, Vol. 4, 1979, pp. 1171-1228; Ollis, W. D.; Ramsden, C. A. Meso-ionic Heterocycles. In Adv. Heterocycl. Chem., Katritzky, A. R.; Boulton, A. J. Eds.; Academic, New York, Vol. 19, 1976, pp. 1-122; Newton, C. G.; Ramsden, C. A. Tetrahedron, 1982, 38, 2965-3011; Ollis, W. D.; Stanforth, S. P. Tetrahedron, 1985, 41, 2239-2329; Gingrich, H. L., Baum, J. S. Mesoionic Oxazoles. In The Chemistry of Heterocyclic Compounds, Turchi, I. D. Ed. Wiley, New York, Vol. 45, 1986, pp. 731-961.
7. Reviews on mesoionic compounds including cycloaddition: Ohta, M.; Kato, H. Sydnones and Other Mesoionic Compounds. In Nonbenzenoid Aromatics, Snyder, J. P. Ed; Academic, New York, 1969, pp. 117-248; Ramsden, C. A. Meso-ionic Heterocycles. In Comprehensive Organic Chemistry, Barton, D. H. R., Ollis, W. D. Eds; Pergamon, Oxford, Vol. 4, 1979, pp. 1171-1228; Ollis, W. D.; Ramsden, C. A. Meso-ionic Heterocycles. In Adv. Heterocycl. Chem., Katritzky, A. R.; Boulton, A. J. Eds.; Academic, New York, Vol. 19, 1976, pp. 1- 122; Newton, C. G.; Ramsden, C. A. Tetrahedron, 1982, 38, 2965-3011; Ollis, W. D.; Stanforth, S. P. Tetrahedron, 1985, 41, 2239-2329; Gingrich, H. L., Baum, J. S. Mesoionic Oxazoles. In The Chemistry of Heterocyclic Compounds, Turchi, I. D. Ed. Wiley, New York, Vol. 45, 1986, pp. 731-961.
8. Reviews on mesoionic compounds including cycloaddition: Ohta, M.; Kato, H. Sydnones and Other Mesoionic Compounds. In Nonbenzenoid Aromatics, Snyder, J. P. Ed; Academic, New York, 1969, pp. 117-248; Ramsden, C. A. Meso-ionic Heterocycles. In Comprehensive Organic Chemistry, Barton, D. H. R., Ollis, W. D. Eds; Pergamon, Oxford, Vol. 4, 1979, pp. 1171-1228; Ollis, W. D.; Ramsden, C. A. Meso-ionic Heterocycles. In Adv. Heterocycl. Chem., Katritzky, A. R.; Boulton, A. J. Eds.; Academic, New York, Vol. 19, 1976, pp. 1- 122; Newton, C. G.; Ramsden, C. A. Tetrahedron, 1982, 38, 2965-3011; Ollis, W. D.; Stanforth, S. P. Tetrahedron, 1985, 41, 2239-2329; Gingrich, H. L., Baum, J. S. Mesoionic Oxazoles. In The Chemistry of Heterocyclic Compounds, Turchi, I. D. Ed. Wiley, New York, Vol. 45, 1986, pp. 731-961.
9. Reviews on mesoionic compounds including cycloaddition: Ohta, M.; Kato, H. Sydnones and Other Mesoionic Compounds. In Nonbenzenoid Aromatics, Snyder, J. P. Ed; Academic, New York, 1969, pp. 117-248; Ramsden, C. A. Meso-ionic Heterocycles. In Comprehensive Organic Chemistry, Barton, D. H. R., Ollis, W. D. Eds; Pergamon, Oxford, Vol. 4, 1979, pp. 1171-1228; Ollis, W. D.; Ramsden, C. A. Meso-ionic Heterocycles. In Adv. Heterocycl. Chem., Katritzky, A. R.; Boulton, A. J. Eds.; Academic, New York, Vol. 19, 1976, pp. 1- 122; Newton, C. G.; Ramsden, C. A. Tetrahedron, 1982, 38, 2965-3011; Ollis, W. D.; Stanforth, S. P. Tetrahedron, 1985, 41, 2239-2329; Gingrich, H. L., Baum, J. S. Mesoionic Oxazoles. In The Chemistry of Heterocyclic Compounds, Turchi, I. D. Ed. Wiley, New York, Vol. 45, 1986, pp. 731-961.
10. Matsukubo, H.; Kato, H. J. Chem. Soc., Chem. Commun., 1974, 412-413; Nakazawa, S.; Hirakawa, K., Kiyosawa, T; Kato, H. J. Chem. Soc., Chem. Commun., 1974, 621; Matsukubo, H.; Kato, H. J. Chem. Soc., Perkin Trans. I, 1975, 632-635; Matsukubo, H.; Kojima, M.; Kato, H. Chemistry Lett., 1975, 1153-1154; Kato, H.; Nakazawa, S.; Kiyosawa, T.; Hirakawa, K. J. Chem. Soc., Perkin Trans. 1, 1976, 672-675; Kobayashi, T.; Minemura, H.; Kato, H. Heterocycles, 1995, 40, 311-317. Cf. Also: Eicher, T.; Schaefer, V. Tetrahedron, 1974, 30, 4025-4029; Potts, K. T.; Baum, J.; Houghton, E. J. Org. Chem., 1976, 41, 818-824.
11. Matsukubo, H.; Kato, H. J. Chem. Soc., Chem. Commun., 1974, 412-413; Nakazawa, S.; Hirakawa, K., Kiyosawa, T; Kato, H. J. Chem. Soc., Chem. Commun., 1974, 621; Matsukubo, H.; Kato, H. J. Chem. Soc., Perkin Trans. I, 1975, 632-635; Matsukubo, H.; Kojima, M.; Kato, H. Chemistry Lett., 1975, 1153-1154; Kato, H.; Nakazawa, S.; Kiyosawa, T.; Hirakawa, K. J. Chem. Soc., Perkin Trans. 1, 1976, 672-675; Kobayashi, T.; Minemura, H.; Kato, H. Heterocycles, 1995, 40, 311-317. Cf. Also: Eicher, T.; Schaefer, V. Tetrahedron, 1974, 30, 4025-4029; Potts, K. T.; Baum, J.; Houghton, E. J. Org. Chem., 1976, 41, 818-824.
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14. Matsukubo, H.; Kato, H. J. Chem. Soc., Chem. Commun., 1974, 412-413; Nakazawa, S.; Hirakawa, K., Kiyosawa, T; Kato, H. J. Chem. Soc., Chem. Commun., 1974, 621; Matsukubo, H.; Kato, H. J. Chem. Soc., Perkin Trans. I, 1975, 632-635; Matsukubo, H.; Kojima, M.; Kato, H. Chemistry Lett., 1975, 1153-1154; Kato, H.; Nakazawa, S.; Kiyosawa, T.; Hirakawa, K. J. Chem. Soc., Perkin Trans. 1, 1976, 672-675; Kobayashi, T.; Minemura, H.; Kato, H. Heterocycles, 1995, 40, 311-317. Cf. Also: Eicher, T.; Schaefer, V. Tetrahedron, 1974, 30, 4025-4029; Potts, K. T.; Baum, J.; Houghton, E. J. Org. Chem., 1976, 41, 818-824.
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32. These results were calculated with precise option by "Pasocon MOP AC/386" which is based on the MOPAC (Ver. 6.0, QCPE No. 455), of Toray System Center.
33. w = 0.067, GOOF = 1.76 for 1707 data [F> 3.00 σ (F)]. Atomic coordinates, bond lengths and angles, and thermal parameters will be deposited at the Cambridge Crystallographic Data Centre.
34. w = 0.083, GOOF = 2.54 for 3270 data [F> 3.00 σ(F)]. Atomic coordinates, bond lengths and angles, and thermal parameters have been deposited at the Cambridge Crystallographic Data Centre. Any request to the CCDC for this material should quote the full literature citation (Ref. 1) and the reference number 182/18.
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