Azatriquinane, azatriquinacene, and a remarkable dimerization product

Tetrahedron Letters

Volumn 37, Issue 1, 1996, Pages 131-134

  Mascal, Mark ^a   Hext, Nicholas M ^a   Shishkin, Oleg V ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; POLYCYCLIC AROMATIC HYDROCARBON;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; X RAY ANALYSIS;

EID: 0030044002     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02091-8     Document Type: Article

References (25)

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2. The fortuitous synthesis of a polycycle containing the [2.2.2]cyclazine ring system has been reported: Lamm, B.; Andersen, L.; Aurell, C.-J. Tetrahedron Lett. 1983, 24, 2413.
3. For a discussion see Paquette, L. A. Chem. Rev. 1989, 89, 1051.
4. Flitsch, W.; Krämer, U. Adv. Heterocycl. Chem. 1978, 22, 321.
5. Crepidine: Elander, M.; Leander, K.; Rosenblom, J.; Ruusa, E. Acta Chem. Scand. 1973, 27, 1907.
6. Coccinelline: (a) Tursch, B.; Daloze, D.; Dupont, M.; Pasteels, J. M.; Tricot, M-C. Experientia 1971, 27, 1380.
7. (b) Ayer, W. A.; Browne, L. M. Heterocycles 1977, 7, 685.
8. Formally pyrrolo[2,1,5-cd]pyrrolizine.
9. (a) Cram, D. J. Science 1983, 279, 1177.
10. (b) Cram, D. J.; Cram, J. M. Container Molecules and Their Guests, Royal Society of Chemistry, Cambridge, 1994.
11. Dietrich, B.; Lehn, J.-M; Sauvage, J.-P.; Blanzat, J. Tetrahedron, 1973, 29, 1629.
12. (a) Rideout, D. C.; Breslow, R. J. Am. Chem. Soc. 1980, 102, 7816.
13. (b) Grieco, P. A.; Yoshida, K.; Garner, P. J. Org. Chem. 1983, 48, 3137.
14. (c) Breslow, R.; Maitra, U.; Rideout, D. Tetrahedron Lett. 1983, 24, 1901.
15. Turner, W. H. J. Heterocyclic Chem. 1986, 23, 327
16. Miyano, S.; Somehara, T.; Nakao, M.; Sumoto, K. Synthesis 1978, 701.
17. Treibs, A.; Michl, K.-H. Liebigs Ann. Chem. 1954, 589, 163.
18. 4 salt, which will be published when the work is presented in full.
19. We define 'simple' as a trialkyl amine whose basicity is not influenced by the presence of other heteroatoms.
20. Formally 1-azabicyclo[2.2.2]octane; a consensus of literature values places the pKa of this compound at about 11.0.
21. Alder, R. W.; Eastment, P.; Hext, N. M.; Moss, R. E.; Orpen, A. G.; White, J. M. J. Chem. Soc., Chem. Commun. 1988, 1528.
22. Method of Barton, D. H. R.; Beugelmans, R.; Young, R. N. Nouv. J. Chim. 1978, 2, 363.
23. 2 = 0.099 (S = 1.018) for 1275 independent reflections.
24. Such dimerizations have been observed for acyclic azomethine ylides: Ouali, M.S.; Vaultier, M.; Carrié, R. Bull. Soc. Chim. Fr. II 1979, 633.
25. 2) 94.0 and 131.0. All other analytical data are consistent with the assigned structure, in particular the IR and UV spectra, which bear a strong resemblance to that of perchlorotriquinacene (Jacobson, I.T. Acta Chem. Scand. 1972, 26, 2477).