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.

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.

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

• Journal Article Type: Article
• Acceptance Date: Nov 5, 2014
• Online Publication Date: Nov 19, 2014
• Publication Date: Dec 1, 2014
• Deposit Date: Sep 28, 2017
• Publicly Available Date: Sep 28, 2017
• 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
• 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
• Public URL: https://nottingham-repository.worktribe.com/output/738917
• Publisher URL: http://scripts.iucr.org/cgi-bin/paper?S205322961402436X
• 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
• Contract Date: Sep 28, 2017