The first report of unusual flipping of the cycloadducts from 1,3-dipolar cycloaddition of 3,4,5,6-tetrahydropyridine N-oxide to N-cinnamoyl piperidines

Tetrahedron Letters

Volumn 47, Issue 23, 2006, Pages 3827-3830

  Banerji, Avijit ^a   Bandyopadhyay, Debasish ^a   Sengupta, Piyali ^a   Basak, Bidyut ^a   Prangé, Thierry ^b   Neuman, Alain ^b  

^a UNIVERSITY OF CALCUTTA   (India)

^b UMR 7013 CNRS   (France)

Author keywords

Dipolar cycloaddition; Intermolecular; Isoxazolidines; Nitrones

Indexed keywords

3,4,5,6 TETRAHYDROPYRIDINE N OXIDE; CINNAMIC ACID; ISOXAZOLIDINE DERIVATIVE; N CINNAMOYLPIPERIDINE DERIVATIVE; PIPERIDINE DERIVATIVE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLOADDITION; SOLID STATE; SUBSTITUTION REACTION; X RAY CRYSTALLOGRAPHY;

EID: 33646163882     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.03.168     Document Type: Article

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26. 2: C, 72.58; H, 8.33; N, 8.91. Found: C, 72.49; H, 8.21; N, 8.73.
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28. 2Cl: C, 65.42; H, 7.22; N, 8.03. Found: C, 65.28; H, 7.13; N, 7.94.
29. 2: C, 72.58; H, 8.33; N, 8.91. Found: C, 72.43; H, 8.25; N, 8.79.
30. 4: C, 63.49; H, 7.01; N, 11.69. Found: C, 63.31; H, 6.84; N, 11.53.
31. For all the three compounds viz., 3a, 4b and 5a, crystal structure data were collected on a Phillips PW1100 four-circle diffractometer and refined using the shelxl program. Wavelength for data recordings is 1.5418 Å (Cu-Kα) and temperature 298 K. Crystallographic data for all three compounds have been deposited with the Cambridge Crystallographic Data Centre as CCDC 236268 (3a), 236271 (4b) and 236270 (5a). Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44 1223 336033 or e-mail: deposit@ccdc.cam.ac.uk).