Ring expansion of heterocyclic ketene N,X-acetals and 2-alkylidenedihydroindoles with methanesulphonyl azide by [3 + 2] cycloaddition and subsequent extrusion of molecular nitrogen

Liebigs Annales

Volumn , Issue 10, 1996, Pages 1541-1549

  Quast, Helmut ^a   Ivanova, Svetlana ^a   Peters, Eva Maria ^b   Peters, Karl ^b   Von Schnering, Hans Georg ^b  

^a UNIVERSITY OF WÜRZBURG   (Germany)

^b MAX PLANCK INSTITUT FÜR FESTKÖRPERFORSCHUNG   (Germany)

Author keywords

1,2 Shift of carbon, nitrogen, sulphur, or selenium; Amidines, cyclic, N sulphonyl ; Azides, electrophilic; Ketene N,X acetals, cyclic; Ring expansion of heterocycles; 3 + 2 Cycloaddition

Indexed keywords

EID: 33749087654     PISSN: 09473440     EISSN: None     Source Type: Journal    
DOI: 10.1002/jlac.199619961008     Document Type: Article

References (41)

1. The results are taken from the projected dissertation by S. Ivanova, University of Würzburg.
2. H Quast M. Ach, M. K. Kindermann, P. Rademacher, M. Schindler, Chem. Ber. 1993, 126, 503-516.
3. For less reactive ketene N,X-acetals, which possess electron-withdrawing groups at the α-carbon atom, see R. W. Saalfrank, M Fischer, U. Wirth, H. Zimmermann, Angew. Chem. 1987, 99 1218-1219;
4. Angew. Chem. Int. Ed. Engl. 1987, 26, 1160-1161;
5. R. W. Saalfrank, U. Wirth, Chem. Ber. 1989, 122, 969-973;
6. R. W. Saalfrank, C.-J. Lurz, U. Wirth, H. G. von Schnering, K. Peters, J. Heterocycl. Chem 1991, 28, 1863-1868;
7. M.-X. Wang, Z.-T. Huang, J. Org. Chem. 1995, 60, 2807-2811, and references cited therein.
8. H. Quast, D. Regnat, E.-M. Peters, K. Peters, H. G. von Schnering, Angew. Chem. 1990, 102, 724-726;
9. Angew. Chem. Int. Ed. Engl. 1990, 29, 695-697.
10. H. Quast M Ach, S. Ivanova, E.-M. Peters, K. Peters, H. O. von Schnering, Liebigs Ann. 1996, 1551-1553, following paper in this issue.
11. H. Quast, D. Regnat, J. Balthasar, K. Banert, E.-M. Peters, K. Peters, H. G. von Schnering, Liebigs Ann. Chem. 1991, 409-416.
12. H. Quast, M. Ach, E.-M. Peters, K. Peters, H. G. von Schnering, Liebigs Ann. Chem. 1992, 1259-1269.
13. C. Reichardt, N. Kaufmann, Chem. Ber. 1985, 118, 3424-3427.
14. J. Metzger, H. Larivé, É.-J. Vincent, R. Dennilauler, J. Chim. Phys. 1963, 60, 944-949.
15. E. Fischer, A. Steche, Liebigs Ann. Chem. 1887, 242, 348-366.
16. C. Reichardt, H. D. Engel, Chem. Ber. 1988, 121, 1009-1011.
17. A. S. Bailey, R. Scattergood, W. A. Warr, J. Chem. Soc. (C) 1971, 3769-3778.
18. J. R. Owen, Tetrahedron Lett. 1969, 2709-2712;
19. Org. Chem. Bull. (Eastman Kodak) 1971, 43, 3-7
20. [Chem. Abstr. 1972, 76, 114815u].
21. C. Reichardt, W. Mormann, Chem. Ber. 1972, 105, 1815-1839.
22. W. König, W. Meier, J. Prakt. Chem. 1925, 109, 324-344;
23. O. Mumm, H. Hinz, J. Diederichsen, Ber. Dtsch. Chem. Ges. 1939, 72, 2107-2120.
24. G. I. Georg, G. C. B. Harriman, S. A. Peterson, J. Org. Chem. 1995, 60, 7366-7368.
25. R. Huisgen, R. Grashey, J. Sauer in The Chemistry of Alkenes (Ed.: S. Patai), Wiley, New York, 1964, p. 835-844;
26. W. Lwowski in 1,3-Dipolar Cycloaddition Chemistry (Ed.: A. Padwa), 1st ed., vol. 1, Ch. 5, Wiley, New York, 1984;
27. P. K. Kadaba, B. Stanovnik, M. Tišler, Adv. Heterocycl. Chem. 1984, 37, 217-349;
28. M. Regitz, G. Maas, Diazo Compounds, 1st ed., Academic Press, New York, 1986, p. 384-389.
29. H. C. van der Plas, Ring Transformation of Heterocycles, 1st. ed., Academic Press, New York, 1973;
30. A. R. Katritzky, Handbook of Heterocyclic Chemistry, 1st. ed., Pergamon Press, Oxford, 1985, p. 388, 396;
31. M. Hesse, Ring Enlargement in Organic Chemistry, 1st ed., VCH, Weinheim, 1991;
32. D. C. Liotta, M. Volmer, Organic Syntheses, Reaction Guide, 1st. ed., Wiley, New York, 1991, p. 112-116;
33. J. K. Crandall, L. C. Crawley, J. B. Komin, J. Org. Chem. 1975, 40, 2045-2047;
34. C. M. Shafer, T. F. Molinski, J. Org. Chem. ibid. 1996, 61, 2044-2050.
35. J. Metzger, H. Plank, Bull. Soc. Chim. Fr. 1956, 1692-1696.
36. N. Suzuki, T. Yamabayashi, Y. Izawa, Bull. Chem. Soc. Jpn. 1976, 49, 353-354.
37. H. Quast, E. Schmitt, Chem. Ber. 1968, 101, 4012-4014.
38. G. Vernin, H. Domlog, C. Siv, J. Metzger, A. K. El-Shafei, J. Heterocycl. Chem. 1981, 18, 85-89.
39. H.-O. Kalinowski, H. Kessler, Org. Magn. Res. 1974, 6,
40. G. M. Sheldrick, University of Göttingen, unpublished results.
41. Further details of the crystal structure investigations are available on request from the Fachinformationszentrum Karlsruhe, D-76344 Eggenstein-Leopoldshafen, on quoting the depository numbers CSD-404783 (16b), -404784 (21b), -404785 (24), and -404782 (27), the names of the authors and the journal citation.