Stereoselective synthesis of conformationally constrained tropane analogues: 6-Chloro-2,5-diazatetracyclo[8.5.0.02,13.0 4,9]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

Jie Cheng; Liang Xu; Edwin D. Stevens; Mark L. Trudell; Sari Izenwasser; Dean Wade

doi:10.1002/jhet.5570410414

Stereoselective synthesis of conformationally constrained tropane analogues: 6-Chloro-2,5-diazatetracyclo[8.5.0.0^2,13.0 ^4,9]pentadeca-4,6,8-triene-11-one and 6-chloro-2,7-diazatetracyclo- [8.5.0.0^2,13.0^4,9]pentadeca-4,6,8-triene-11-one

Jie Cheng, Liang Xu, Edwin D. Stevens, Mark L. Trudell, Sari Izenwasser, Dean Wade

Psychiatry & Behavioral Sciences

Research output: Contribution to journal › Article › peer-review

4 Scopus citations

Abstract

Two conformationally constrained tropane derivatives were prepared as rigid nicotinic acetylcholine receptor ligands. A palladium catalyzed intramolecular α-arylation reaction was employed to generate the tricyclic compounds in good yields from N-(bromo-chloropyridylmethyl)-8-azabicyclo[3.2.1]octan-3-ones.

Original language	English (US)
Pages (from-to)	569-574
Number of pages	6
Journal	Journal of Heterocyclic Chemistry
Volume	41
Issue number	4
DOIs	https://doi.org/10.1002/jhet.5570410414
State	Published - Jan 1 2004

ASJC Scopus subject areas

Organic Chemistry

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Cheng, J., Xu, L., Stevens, E. D., Trudell, M. L., Izenwasser, S., & Wade, D. (2004). Stereoselective synthesis of conformationally constrained tropane analogues: 6-Chloro-2,5-diazatetracyclo[8.5.0.0^2,13.0 ^4,9]pentadeca-4,6,8-triene-11-one and 6-chloro-2,7-diazatetracyclo- [8.5.0.0^2,13.0^4,9]pentadeca-4,6,8-triene-11-one. Journal of Heterocyclic Chemistry, 41(4), 569-574. https://doi.org/10.1002/jhet.5570410414

Stereoselective synthesis of conformationally constrained tropane analogues : 6-Chloro-2,5-diazatetracyclo[8.5.0.0^2,13.0 ^4,9]pentadeca-4,6,8-triene-11-one and 6-chloro-2,7-diazatetracyclo- [8.5.0.0^2,13.0^4,9]pentadeca-4,6,8-triene-11-one. / Cheng, Jie; Xu, Liang; Stevens, Edwin D.; Trudell, Mark L.; Izenwasser, Sari; Wade, Dean.

In: Journal of Heterocyclic Chemistry, Vol. 41, No. 4, 01.01.2004, p. 569-574.

Research output: Contribution to journal › Article › peer-review

Cheng, J, Xu, L, Stevens, ED, Trudell, ML, Izenwasser, S & Wade, D 2004, 'Stereoselective synthesis of conformationally constrained tropane analogues: 6-Chloro-2,5-diazatetracyclo[8.5.0.0^2,13.0 ^4,9]pentadeca-4,6,8-triene-11-one and 6-chloro-2,7-diazatetracyclo- [8.5.0.0^2,13.0^4,9]pentadeca-4,6,8-triene-11-one', Journal of Heterocyclic Chemistry, vol. 41, no. 4, pp. 569-574. https://doi.org/10.1002/jhet.5570410414

Cheng J, Xu L, Stevens ED, Trudell ML, Izenwasser S, Wade D. Stereoselective synthesis of conformationally constrained tropane analogues: 6-Chloro-2,5-diazatetracyclo[8.5.0.0^2,13.0 ^4,9]pentadeca-4,6,8-triene-11-one and 6-chloro-2,7-diazatetracyclo- [8.5.0.0^2,13.0^4,9]pentadeca-4,6,8-triene-11-one. Journal of Heterocyclic Chemistry. 2004 Jan 1;41(4):569-574. https://doi.org/10.1002/jhet.5570410414

Cheng, Jie ; Xu, Liang ; Stevens, Edwin D. ; Trudell, Mark L. ; Izenwasser, Sari ; Wade, Dean. / Stereoselective synthesis of conformationally constrained tropane analogues : 6-Chloro-2,5-diazatetracyclo[8.5.0.0^2,13.0 ^4,9]pentadeca-4,6,8-triene-11-one and 6-chloro-2,7-diazatetracyclo- [8.5.0.0^2,13.0^4,9]pentadeca-4,6,8-triene-11-one. In: Journal of Heterocyclic Chemistry. 2004 ; Vol. 41, No. 4. pp. 569-574.

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