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
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-carboxylat...
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| Format: | Article |
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International Union of Crystallography
2014
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| Online Access: | https://eprints.nottingham.ac.uk/46628/ |
| _version_ | 1848797371500068864 |
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| author | Schwehm, Carolin Lewis, William Blake, Alexander J. Kellam, Barrie Stocks, Michael J. |
| author_facet | Schwehm, Carolin Lewis, William Blake, Alexander J. Kellam, Barrie Stocks, Michael J. |
| author_sort | Schwehm, Carolin |
| building | Nottingham Research Data Repository |
| collection | Online Access |
| description | 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. |
| first_indexed | 2025-11-14T20:02:49Z |
| format | Article |
| id | nottingham-46628 |
| institution | University of Nottingham Malaysia Campus |
| institution_category | Local University |
| last_indexed | 2025-11-14T20:02:49Z |
| publishDate | 2014 |
| publisher | International Union of Crystallography |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | nottingham-466282020-05-04T16:56:49Z https://eprints.nottingham.ac.uk/46628/ 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. 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. International Union of Crystallography 2014-12-01 Article PeerReviewed Schwehm, Carolin, Lewis, William, Blake, Alexander J., Kellam, Barrie and Stocks, Michael 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). pp. 1161-1168. ISSN 2053-2296 X-ray crystal structure; privileged structure; bicycle formation; biologically active compounds; NMR evaluation; medicinal chemistry; GPCRs; polycyclic scaffolds http://scripts.iucr.org/cgi-bin/paper?S205322961402436X doi:10.1107/S205322961402436X doi:10.1107/S205322961402436X |
| spellingShingle | X-ray crystal structure; privileged structure; bicycle formation; biologically active compounds; NMR evaluation; medicinal chemistry; GPCRs; polycyclic scaffolds Schwehm, Carolin Lewis, William Blake, Alexander J. Kellam, Barrie Stocks, Michael J. 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 |
| title | 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 |
| title_full | 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 |
| title_fullStr | 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 |
| title_full_unstemmed | 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 |
| title_short | 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 |
| title_sort | 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 |
| topic | X-ray crystal structure; privileged structure; bicycle formation; biologically active compounds; NMR evaluation; medicinal chemistry; GPCRs; polycyclic scaffolds |
| url | https://eprints.nottingham.ac.uk/46628/ https://eprints.nottingham.ac.uk/46628/ https://eprints.nottingham.ac.uk/46628/ |