Unexpected cycloadducts from 1,3-dipolar cycloaddition of 3,4-dehydromorpholine N-oxide to N-cinnamoyl piperidines-first report of the novel formation of 2:1 cycloadducts

Tetrahedron Letters

Volumn 46, Issue 15, 2005, Pages 2619-2622

  Banerji, Avijit ^a   Bandyopadhyay, Debasish ^a   Prangé, Thierry ^b   Neuman, Alain ^b  

^a UNIVERSITY OF CALCUTTA   (India)

^b CNRS UMR9187   (France)

Author keywords

Dipolar cycloaddition; Intermolecular; Isoxazolooxazines; Nitrone

Indexed keywords

3,4 DEHYDROMORPHOLIN N OXIDE; CINNAMIC ACID; CINNAMIC ACID DERIVATIVE; MORPHOLINE DERIVATIVE; PIPERIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLOADDITION; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 15244360268     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.02.083     Document Type: Article

References (19)

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13. 5: C, 63.29; H, 7.48; N, 10.06. Found: C, 63.21; H, 7.37; N, 10.15
14. 5Cl: C, 58.47; H, 6.64; N, 9.30. Found: C, 58.59; H, 6.73; N, 9.03.
15. 6: C, 61.73; H, 7.43; N, 9.39. Found: C, 61.52; H, 7.31; N, 9.44
16. 7: C, 57.13; H, 6.54; N, 12.11. Found: C, 57.01; H, 6.63; N, 12.08
17. 4: C, 65.88; H, 7.56; N, 8.09. Found: C, 66.07; H, 7.37; N, 7.86
18. α radiation (1.541 Å). The structures were solved by direct methods and refined with isotropic, then anisotropic thermal factors by full-matrix least squares techniques. All hydrogen atoms were calculated at their theoretical places and their positional parameters were refined. Crystallographic data for both the compounds 4a and 3c, have been deposited with the Cambridge Crystallographic Data Centre as CCDC 235158 (4a) and 235157 (3c). 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)
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