Regiochemistry of addition of aminoheterocycles to α-cyanocinnamonitriles: formation of aza-bridged bi- and tricycles

Tetrahedron Letters

Volumn 48, Issue 36, 2007, Pages 6360-6363

  Wendt, Michael D ^a   Kunzer, Aaron ^a   Henry, Rodger F ^a   Cross, Jeffrey ^a   Pagano, Thomas G ^a  

^a ABBOTT LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA CYANOCINNAMONITRILE; AMINOINDAZOLE; AMINOPYRAZOLE; HETEROCYCLIC AMINE; NITRILE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; AUTOOXIDATION; CHEMICAL STRUCTURE; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; RING CLOSING METATHESIS; X RAY CRYSTALLOGRAPHY;

EID: 34547667549     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.07.039     Document Type: Article

References (21)

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20. Genreal procedures: Reactions with 2a: A solution of heterocyclic amine (1 mmol), 2a (1 mmol), and base (1 mmol) in 5 mL absolute ethanol was refluxed for 24 h. Products were obtained by chromatography on silica gel, or triturated by addition of ether to the cooled reaction mixture. Reactions with 2b: A solution of heterocyclic amine (1 mmol), 2b (1 mmol), and base (1 mmol) in 5 mL absolute ethanol was refluxed in open air for 1-24 h, following progress by LC-MS. In cases where autoxidation occurred, products were obtained as above. Where unoxidized products were formed, chromatography was followed by taking up the pure unoxidized product in DCM (5 mL) and water (2 mL) and stirring with DDQ (1 equiv) for 10 min. The layers were then separated and the final product subjected to chromatography through a short silica gel column.
21. Crystallographic data (excluding structure factors) for the structures in this Letter have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC 648309-648313 for 3c, 5, 4b, 8, and 6, consecutively. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44(0) 1223 336033 or e-mail: deposit@ccdc.cam.ac.uk].