An intramolecular 1-azadiene Diels-Alder approach to the preparation of synthetic equivalents of pyridine

Tetrahedron Letters

Volumn 40, Issue 40, 1999, Pages 7211-7214

  Motorina, Irina A ^a   Grierson, David S ^a  

^a INSTITUT DE CHIMIE DES SUBSTANCES NATURELLES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; BENZALDEHYDE; PIPERIDINE; PYRIDINE DERIVATIVE;

ARTICLE; CHEMICAL MODIFICATION; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033215198     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01463-X     Document Type: Article

References (14)

1. a) Royer, J.; Husson, H-P. Advances in the Use of Synthons in Organic Synthesis 1995, 2, 1-68. Dondoni, A. Ed. Jai Press, London.
2. b) Maury, C.; Wong, Q.; Tgharbaoui, T.; Chiadmi, M.; Tomas, A. Royer, J.; Husson, H-P. Tetrahedron, 1997, 53, 3627-3636.
3. a) Sisti, N.J.; Zeller, E.; Grierson, D.S.; Fowler, F.W. J. Org. Chem., 1997, 62, 2093-2097.
4. b) Motorina, I.A.; Fowler, F.W.; Grierson, D.S. J. Org. Chem., 1997, 62, 2097-2105.
5. Grierson, D.S.; Harris, M.; Husson, H.-P. J. Am. Chem. Soc., 1980, 102, 1064-1082.
6. a) Schwarz, J.B.; Devine, P.N.; Meyers, A.I. Tetrahedron, 1997, 53, 8795-8806.
7. b) Schwarz, J.B.; Meyers, A.I. J. Org. Chem., 1998, 63, 1619-1629.
8. a) Ahlbrecht, H.; Vonderheid, C. Synthesis, 1975, 512-515.
9. b) Ahlbrecht, H.; Liesching, D. Synthesis, 1977, 495-496
10. Sisti, N.J.; Motorina, I.A.; Tran Huu Dau, M.E.; Riche, C.; Fowler, F.W.; Grierson, D.S. J. Org. Chem., 1996, 61, 3715-3728.
11. For analogous intramolecular reaction of nucleophilic nitrogen with trifloyl imidates, see: Goulaouic-Dubois, C.; Adams, D.; Sisti, N.J.; Fowler, F.W.; Grierson, D.S. Tetrahedron Lett., 1998, 39, 4283-4286.
12. Azadiene 13c, bearing a C-4 methyl group was heated at different temperatures and times to study its reactivity with respect to imine to enamine tautomerization. Thus, on heating a 0.02 M solution of 13c in benzene at 110°C for 24 h the Diels-Alder product 16c (4,6-trans/4,6-cis : 2/1) was obtained (71%) along with some amount of the cyclized enamine 21 (11%), whereas, on heating at 60°C for 24h only a slow conversion to the enamine product 21 occurred (11%). (formula presented)
13. Schwesinger, R.; Hasenfratz, C.; Schlemper, H.; Walz, L.; Peters, E-M.; Peters, K.; von Schnering, H.G. Angew. Chem. Int. Ed. Engl., 1993, 32, 1361-1363.
14. 3) δ 24.83 (C3), 32.79 (C9), 49.29 (C4), 56.49 (OMe), 68.32 (C2), 68.90 C8), 84.17 (C10), 114.93 (CN), 115.30 (C7), 121.85 (C6).