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This review summarises the structure, basicity, asymmetric organocatalysis, synthesis and reactions of quinuclidines. Quinuclidines are bicyclic saturated pyridin-containing compounds with rigid structures and a ring-juncture nitrogen atom. This review covers the period from 1984-2005.

1-azabicyclo[2.2.2]octan-3-one. HCl (1) reacts with ylidene nitrile through photo- thermal reaction conditions to give 4-benzyl-5-imino-3-phenyl-6-oxa-1-aza-tricyclo[6.2.2.02,7]dodec-2(7)-ene-4-carbonitrile. (3) via intermolecular double Micheal reaction, whereas, 5-imino-3-phenyl-6-oxa-1-azatricyclo[6.2.2.02,7]dodec-2(7)-ene-4-carbonitrile (4) was achieved via thermal conditions only.

The (Z)-2-arylidene-quinuclidines 5 - 8 were synthesized. Their reaction with aliphatic dibasic functional reagents in both basic and acidic conditions afforded the fused heterocycles 9, 10 and 11. However, the reaction of arylidene derivative 5 with an aromatic dibasic functional reagent gave benzimidazole 13 in lieu of the anticipated tetracyclic system, quinuclidino[3,2-e]benzo[b]-1,4-diazepine 12. Cycloadditions of 5 with different reagents gave the heterocyclic derivatives 17, 19, 22 and 23. Acid-catalyzed cyclization of 5 with excess resorcinol gave 24. Compounds 9a, 19 and 24 showed antibacterial activities.

Pyridine derivatives with bridges R 0460 Intermolecular Double Michael Reaction to Construct 4-Benzyl-5-imino-3-phenyl-6-oxa-1-aza-tricyclo[6.2.2.0 2,7 ]dodec-2(7)-ene-4-carbonitrile. -The different behavior of the quinuclidine derivative (I) is explained on the basis of MO calculations. -(ZOOROB, H. H.; HAMAMA*, W. S.; EL-MAGID, O. M. A.; SOLIMAN, M. S.; J. Chem. Res. 2005, 10, 669-672; Dep. Chem., Fac. Sci., Mansoura Univ., Mansoura, Egypt; Eng.) -H. Haber 09-161