Intramolecular Diels-Alder Reaction of N-Alkyl-2-cyano-1-azadienes: A Study of the Eschenmoser Cycloreversion of Dihydrooxazines as a Route to N-Alkyl-2-cyano-1-azadienes

Journal of Organic Chemistry

Volumn 62, Issue 7, 1997, Pages 2098-2105

  Motorina, Irina A ^c   Fowler, Frank W ^b   Grierson, David S ^a  

^a INSTITUT DE CHIMIE DES SUBSTANCES NATURELLES   (France)

^b STONY BROOK UNIVERSITY   (United States)

^c NONE

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000947985     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9614046     Document Type: Article

References (46)

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2. (a) Boger, D. L.; Kasper, A. M. J. Am. Chem. Soc. 1989, 111, 1517.
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7. (b) Cheng, T.-S.; Lupo, A. T.; Fowler, F. W. J. Am. Chem. Soc. 1983, 105, 7696.
8. (a) Serckx-Poncin, B.; Hesbain-Frisque, A.-M.; Ghosez, L. Tetrahedron Lett. 1982, 23, 3261.
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10. Boger, D. L.; Corbett, W. L.; Allcock, S. J.; Gilchrist, T. L.; Shattleworth, S. J. Tetrahedron 1991, 48, 10053. See also ref 3a.
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15. (e) Sisti, N. J.; Motorina, I. A.; Tran Huu Dau, M.-E.; Claude, R.; Fowler, F. W.; Grierson, D. S. J. Org. Chem. 1996, 61, 3715.
16. Dufour, B.; Motorina, I.; Fowler, F. W.; Grierson, D. S. Heterocycles 1994, 37, 1455.
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18. For the preparation of LiCN, see: Livinghouse, T. Org. Synth. 1981, 60, 126.
19. De Corte, B.; Denis, J.-M.; De Kimpe, N. J. Org. Chem. 1987, 52, 1147.
20. (a) Gygax, P.; Das Gupta, T. K.; Eschenmoser, A. Helv. Chim. Acta 1972, 55, 2205.
21. b) Kempe, U. M.; Das Gupta, T. K.; Blatt, P.; Gygax, P.; Felix, D.; Eschenmoser, A. Helv. Chim. Acta 1972, 55, 2187.
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30. The authors have deposited atomic coordinates for compound 19 with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
31. Lee, V. J.; Woodward, R. B. J. Org. Chem. 1979, 44, 2487.
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37. + ion.
38. Magrath, J.; Fowler, F. W. Tetrahedron Lett. 1988, 29, 2171.
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40. In the presence of air, hydroxylamine 24 readily cyclizes to 2,5-dimethyl-N-hydroxypyrrolidine; see ref 20 and the following: (a) Oppolzer, W.; Siles, S.; Snowden, L.; Baker, B. H.; Petrzilka, M. Tetrahedron, 1985, 41, 3497. (b) House, H. O.; Manning, D. T.; Mellio, D. G.; Lee, L. F.; Haynes, O. R.; Wilkes, B. E. J. Org. Chem. 1976, 41, 855.
41. In the presence of air, hydroxylamine 24 readily cyclizes to 2,5-dimethyl-N-hydroxypyrrolidine; see ref 20 and the following: (a) Oppolzer, W.; Siles, S.; Snowden, L.; Baker, B. H.; Petrzilka, M. Tetrahedron, 1985, 41, 3497. (b) House, H. O.; Manning, D. T.; Mellio, D. G.; Lee, L. F.; Haynes, O. R.; Wilkes, B. E. J. Org. Chem. 1976, 41, 855.
42. 13C NMR spectra for compound 25. This is ascribed to both amide rotamers and the presence of H-bonded species in the sample analyzed.
43. CAUTION: As the internal pressure increases in the closed tube upon heating, the cycloaddition reaction should be carried out in an isolated fume cupboard and behind a protective screen. Open only after cooling the tube to room temperature.
44. Separation of the diastereoisomers may be achieved by HPLC. For conditions, see ref 8.
45. Negishi, E. Tetrahedron Lett. 1979, N10, 845.
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