Reaction of 2,2,6-trimethyl-4H-1,3-dioxin-4-one with imines: An easy route to enamides

Tetrahedron Letters

Volumn 37, Issue 41, 1996, Pages 7429-7432

  D'Annibale, Andrea ^a   Pesce, Antonella ^a   Resta, Stefano ^a   Trogolo, Corrado ^a  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

2 AZETIDINONE DERIVATIVE; AMIDE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0030574016     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01603-6     Document Type: Article

References (20)

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13. b): Hyatt, J. A.; Raynolds, P. W. In Organic Reactions, Paquette, L. A. Editor; Wiley & Sons: New York 1994; Vol. 45, 159-636.
14. 13. Sato, M.; Ogasawara, H.; Yoshizumi, E.; Kato, T. Chem Pharm. Bull. 1983, 31, 1902-1909.
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18. 17. A tipical experimental procedure is as follows: to a solution of imine (5 mmol) in 5 ml toluene was added 2,2,6-trimethyl-4H-1,3-dioxin-4-one 1 (5 mmol, 0.71 g) at room temperature. The reaction mixture was flushed with argon and immersed in an oil bath heated at 150 °C, and refluxed for 30 min; toluene was then evaporated and the residue poured on a silica gel column eluted with dichloromethane. Enamidic products were obtained as oils.
19. 2= 5.6 Hz), 5.62 (1H, t, J= 1.3 Hz), 7.0-7.4 (10H, m).
20. 19. D'Annibale, A.; Resta, S.; Trogolo, C., unpublished results.