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2004
Alkaloids
U 0600
52- 181
Stereoselective Synthesis of Conformationally Constrained Tropane Analogues:
6-Chloro-2,5-diazatetracyclo[8.5.0.02,13.04,9]pentadeca-4,6,8-triene-11-one and
6-Chloro-2,7-diazatetracyclo[8.5.0.02,13.04,9]pentadeca-4,6,8-triene-11-one. — Two
conformationally constrained homologues of epibatidine, title compound (VII) and its
2,7-diaza isomer, are synthesized employing a palladium-catalyzed intramolecular
α-arylation to generate the tricyclic compounds. The α-arylation reaction proceeds
regioselectively and the reversed regioselectivity observed for (VI) in the intramolecular C—C coupling reaction is likely due to the thermodynamic preference of the system to form the 6-membered ring of (VII) over the less stable 7-membered ring. The
constrained derivatives display very poor binding affinity for neuronal nicotinic acetylcholine receptors which may be due to the conformational or substituent effects introduced by the carbonyl group. — (CHENG, J.; XU, L.; STEVENS, E. D.; TRUDELL*,
M. L.; IZENWASSER, S.; WADE, D.; J. Heterocycl. Chem. 41 (2004) 4, 569-574;
Dep. Chem., Univ. New Orleans, New Orleans, LA 70148, USA; Eng.) —
H. Hoennerscheid
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