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Preparation and structural analysis of (±)-cis-ethyl 2-sulfanylidenedecahydro-1,6-naphthyridine-6-carboxylate and (±)-trans-ethyl 2-oxooctahydro-1H-pyrrolo[3,2-c]pyridine-5-carboxylate

Schwehm, Carolin; Lewis, William; Blake, Alexander J.; Kellam, Barrie; Stocks, Michael J.

Authors

Carolin Schwehm

William Lewis

Alexander J. Blake

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BARRIE KELLAM BARRIE.KELLAM@NOTTINGHAM.AC.UK
Professor of Medicinal Chemistry

MICHAEL STOCKS MICHAEL.STOCKS@NOTTINGHAM.AC.UK
Professor of Medicinal Chemistryand Drug Discovery



Abstract

Bicycle ring closure on a mixture of (4aS,8aR)- and (4aR,8aS)-ethyl 2-oxodecahydro-1,6-naphthyridine-6-carboxylate, followed by conversion of the separated cis and trans isomers to the corresponding thioamide derivatives, gave (4aSR,8aRS)-ethyl 2-sulfanylidenedecahydro-1,6-naphthyridine-6-carboxylate, C11H18N2O2S. Structural analysis of this thioamide revealed a structure with two crystallographically independent conformers per asymmetric unit (Z′ = 2). The reciprocal bicycle ring closure on (3aRS,7aRS)-ethyl 2-oxooctahydro-1H-pyrrolo[3,2-c]pyridine-5-carboxyl-ate, C10H16N2O3, was also accomplished in good overall yield. Here the five-membered ring is disordered over two positions, so that both enantiomers are represented in the asymmetric unit. The compounds act as key intermediates towards the synthesis of potential new polycyclic medicinal chemical structures.

Journal Article Type Article
Publication Date Dec 1, 2014
Journal Acta Crystallographica Section C Structural Chemistry
Electronic ISSN 2053-2296
Publisher International Union of Crystallography
Peer Reviewed Peer Reviewed
Volume 70
Issue 12
Pages 1161-1168
APA6 Citation Schwehm, C., Lewis, W., Blake, A. J., Kellam, B., & Stocks, M. J. (2014). Preparation and structural analysis of (±)-cis-ethyl 2-sulfanylidenedecahydro-1,6-naphthyridine-6-carboxylate and (±)-trans-ethyl 2-oxooctahydro-1H-pyrrolo[3,2-c]pyridine-5-carboxylate. Acta Crystallographica Section C: Structural Chemistry, 70(12), 1161-1168. https://doi.org/10.1107/s205322961402436x
DOI https://doi.org/10.1107/s205322961402436x
Keywords X-ray crystal structure; privileged structure; bicycle formation; biologically active compounds; NMR evaluation; medicinal chemistry; GPCRs; polycyclic scaffolds
Publisher URL http://scripts.iucr.org/cgi-bin/paper?S205322961402436X
Copyright Statement Copyright information regarding this work can be found at the following address: http://eprints.nottingh.../end_user_agreement.pdf
Additional Information Publication: Acta Crystallographica Section C: Structural Chemistry; Content type: research papers; Article metrics: Available; Peer reviewed: Yes; Review process: Single blind; Received: 8 September 2014; Accepted: 5 November 2014; Published online: 19 November 2014; Supplementary materials: This article has supporting information; Copyright: © 2014 International Union of Crystallography

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Copyright Statement
Copyright information regarding this work can be found at the following address: http://eprints.nottingham.ac.uk/end_user_agreement.pdf





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