Synthesis and Structural Properties of Bridged 1,8-Diazacyclotetradeca-4,11-diynes

European Journal of Organic Chemistry

Volumn , Issue 12, 1998, Pages 2803-2809

  Wolfart, Volker ^a   Gleiter, Rolf ^a   Irngartinger, Hermann ^a   Oeser, Thomas ^a   Krieger, Claus ^b  

^a UNIVERSITY OF HEIDELBERG   (Germany)

^b MAX PLANCK INSTITUTE FOR MEDICAL RESEARCH   (Germany)

Author keywords

Alkynes; Cyclizations; Nitrogen heterocycles

Indexed keywords

EID: 0002192851     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0690(199812)1998:12<2803::aid-ejoc2803>3.0.co;2-c     Document Type: Article

References (32)

1. [1a] R. K. Harris, R. A. Spragg, J. Chem. Soc. B 1968, 684.
2. [1b] R. O. Hutchins, D. L. Kopp, E. L. Eliel, J. Am. Chem. Soc. 1968, 90, 7174.
3. [1c] P. J. Crowley, M. J. T. Robinson, M. G. Ward, Chem. Soc., Chem. Commun. 1974, 825.
4. [1d] E. L. Eliel, F. W. Vierhapper, J. Am. Chem. Soc. 1975, 97, 2424.
5. [1e] D. C. Appleton, J. McKenna, J. M. McKenna, L. B. Sims, A. R. Walley, J. Am. Chem. Soc. 1976, 98, 292.
6. [1f] F. A. Anet, I. Yavari, Tetrahedron Lett. 1976, 17, 2093.
7. [1g] F. A. Anet, I. Yavari, J. Am. Chem. Soc. 1977, 99. 2794.
8. Reviews: [2a] J. B. Lambert, S. I. Featherman, Chem. Rev. 1975, 75, 611. - [2b] I. D. Blackburne, A. R. Katritzky, Y. Takeuchi, Acc. Chem Res. 1975, 8, 300. - [2c] M. Rubiralta, E. Giralt, A. Diez, Piperdine. Elsevier, Amsterdam, 1991. - [2d] J.-J. Delpuech in Cyclic Organonitrogen Stereodynamics (Eds.: J. B. Lambert, Y. Takeuchi, Eds), Verlag Chemie, Weinheim, 1992, chapter 7. - [2e] T. A. Crabb, A. R. Katritzky, Adv. Heterocycl. Chem 1984, 36, 3.
9. Reviews: [2a] J. B. Lambert, S. I. Featherman, Chem. Rev. 1975, 75, 611. - [2b] I. D. Blackburne, A. R. Katritzky, Y. Takeuchi, Acc. Chem Res. 1975, 8, 300. - [2c] M. Rubiralta, E. Giralt, A. Diez, Piperdine. Elsevier, Amsterdam, 1991. - [2d] J.-J. Delpuech in Cyclic Organonitrogen Stereodynamics (Eds.: J. B. Lambert, Y. Takeuchi, Eds), Verlag Chemie, Weinheim, 1992, chapter 7. - [2e] T. A. Crabb, A. R. Katritzky, Adv. Heterocycl. Chem 1984, 36, 3.
10. Reviews: [2a] J. B. Lambert, S. I. Featherman, Chem. Rev. 1975, 75, 611. - [2b] I. D. Blackburne, A. R. Katritzky, Y. Takeuchi, Acc. Chem Res. 1975, 8, 300. - [2c] M. Rubiralta, E. Giralt, A. Diez, Piperdine. Elsevier, Amsterdam, 1991. - [2d] J.-J. Delpuech in Cyclic Organonitrogen Stereodynamics (Eds.: J. B. Lambert, Y. Takeuchi, Eds), Verlag Chemie, Weinheim, 1992, chapter 7. - [2e] T. A. Crabb, A. R. Katritzky, Adv. Heterocycl. Chem 1984, 36, 3.
11. Reviews: [2a] J. B. Lambert, S. I. Featherman, Chem. Rev. 1975, 75, 611. - [2b] I. D. Blackburne, A. R. Katritzky, Y. Takeuchi, Acc. Chem Res. 1975, 8, 300. - [2c] M. Rubiralta, E. Giralt, A. Diez, Piperdine. Elsevier, Amsterdam, 1991. - [2d] J.-J. Delpuech in Cyclic Organonitrogen Stereodynamics (Eds.: J. B. Lambert, Y. Takeuchi, Eds), Verlag Chemie, Weinheim, 1992, chapter 7. - [2e] T. A. Crabb, A. R. Katritzky, Adv. Heterocycl. Chem 1984, 36, 3.
12. Reviews: [2a] J. B. Lambert, S. I. Featherman, Chem. Rev. 1975, 75, 611. - [2b] I. D. Blackburne, A. R. Katritzky, Y. Takeuchi, Acc. Chem Res. 1975, 8, 300. - [2c] M. Rubiralta, E. Giralt, A. Diez, Piperdine. Elsevier, Amsterdam, 1991. - [2d] J.-J. Delpuech in Cyclic Organonitrogen Stereodynamics (Eds.: J. B. Lambert, Y. Takeuchi, Eds), Verlag Chemie, Weinheim, 1992, chapter 7. - [2e] T. A. Crabb, A. R. Katritzky, Adv. Heterocycl. Chem 1984, 36, 3.
13. J. Ritter, R. Gleiter, H. Irngartinger, T. Oeser, J. Am. Chem. Soc. 1997, 119, 10599.
14. R. Gleiter, K. Hövermann, J. Ritter, B. Nuber, Angew. Chem. 1995, 107, 867; Angew. Chem. Int. Ed. Engl. 1995, 34, 789.
15. R. Gleiter, K. Hövermann, J. Ritter, B. Nuber, Angew. Chem. 1995, 107, 867; Angew. Chem. Int. Ed. Engl. 1995, 34, 789.
16. W. N. Smith, O. F. Beumel, Synthesis 1974, 441.
17. H. Musso, M. Brudermüller, Chem. Ber. 1988, 121, 2239.
18. R. Gleiter, V. Wolfart, Tetrahedron Lett. 1996, 37, 479.
19. H. Lindlar, Helv. Chim. Acta 1952, 35, 446; N. A. Dobson, G. Eglinton, M. Krishnamurti, R. A. Raphael, R. G. W. Illis, Tetrahedron 1961, 16, 16.
20. H. Lindlar, Helv. Chim. Acta 1952, 35, 446; N. A. Dobson, G. Eglinton, M. Krishnamurti, R. A. Raphael, R. G. W. Illis, Tetrahedron 1961, 16, 16.
21. V. Wolfart, R. Gleiter, C. Krieger, H. Pritzkow, Tetrahedron Lett. 1998, 39, 513.
22. R. Gleiter, M. Ramming, H. Weigl, V. Wolfart, H. Irngartinger, T. Oeser, Liebigs Ann. 1997, 1545.
23. J. Dale, Angew. Chem. 1966, 78, 1070; Angew. Chem. Int. Ed. Engl 1966, 5, 1000.
24. J. Dale, Angew. Chem. 1966, 78, 1070; Angew. Chem. Int. Ed. Engl 1966, 5, 1000.
25. SPARTAN, IBM Release 3.1.7.
26. R. W. Alder, S. P. East, Chem. Rev. 1996, 96, 2097; R. W. Alder, Tetrahedron 1990, 46, 683; Acc. Chem. Res. 1983, 16, 3d.
27. R. W. Alder, S. P. East, Chem. Rev. 1996, 96, 2097; R. W. Alder, Tetrahedron 1990, 46, 683; Acc. Chem. Res. 1983, 16, 3d.
28. R. W. Alder, S. P. East, Chem. Rev. 1996, 96, 2097; R. W. Alder, Tetrahedron 1990, 46, 683; Acc. Chem. Res. 1983, 16, 3d.
29. G. M Sheldrick, SHELXS-97, Universität Göttingen, Germany, 1997.
30. A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi, M. C. Burla, G. Polidori, M. Camalli, SIR-92, Ist. di Ric per lo Sviluppo di Metodologie Cristallografiche, CNR, Univ. of Bari, Italy, 1992.
31. G. M. Sheldrick, SHELXL-93 and SHELXL-97, Universität Göttingen, Germany, 1993 and 1997.
32. C. K. Fair, MOLEN, Enraf-Nonius, Delft, The Netherlands, 1990.