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 and Lewis, William and Blake, Alexander J. and 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

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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.

Item Type: Article
Keywords: X-ray crystal structure; privileged structure; bicycle formation; biologically active compounds; NMR evaluation; medicinal chemistry; GPCRs; polycyclic scaffolds
Schools/Departments: University of Nottingham, UK > Faculty of Science > School of Chemistry
University of Nottingham, UK > Faculty of Science > School of Pharmacy
Identification Number: 10.1107/S205322961402436X
Depositing User: Lewis, William
Date Deposited: 28 Sep 2017 12:46
Last Modified: 14 Oct 2017 08:22
URI: http://eprints.nottingham.ac.uk/id/eprint/46628

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