Diels-Alder reactions of N-acetyl-2-azetine

Tetrahedron Letters

Volumn 40, Issue 3, 1999, Pages 443-446

  Dave, Paritosh R ^b   Duddu, Rajagopal ^b   Surapaneni, Rao ^b   Gilardi, Richard ^a  

^a NAVAL RESEARCH LABORATORY   (United States)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

AZETIDINE DERIVATIVE; N ACETYL 2 AZETINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CYCLIZATION; DIMERIZATION; MOLECULAR INTERACTION; STEREOCHEMISTRY; SYNTHESIS;

BETULACEAE;

EID: 0033555635     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02506-4     Document Type: Article

References (10)

1. Martin, S.F.; Chih-yun, T.; Michio, K.; Simonsen, S.H. J. Org. Chem. 1982, 47, 3634; S.F.; Chih-yun, T. J. Org. Chem. 1981, 46, 3763; Martin, S.F.; Desai, S.R.; Phillips, G.W.; Miller, A.C. J. Am. Chem. Soc. 1980, 102, 3294.
2. Martin, S.F.; Chih-yun, T.; Michio, K.; Simonsen, S.H. J. Org. Chem. 1982, 47, 3634; S.F.; Chih-yun, T. J. Org. Chem. 1981, 46, 3763; Martin, S.F.; Desai, S.R.; Phillips, G.W.; Miller, A.C. J. Am. Chem. Soc. 1980, 102, 3294.
3. Martin, S.F.; Chih-yun, T.; Michio, K.; Simonsen, S.H. J. Org. Chem. 1982, 47, 3634; S.F.; Chih-yun, T. J. Org. Chem. 1981, 46, 3763; Martin, S.F.; Desai, S.R.; Phillips, G.W.; Miller, A.C. J. Am. Chem. Soc. 1980, 102, 3294.
4. Whitney, R.A. Tetrahedron Lett. 1981, 22, 2063.
5. For example Bueno, M.P.; Cativiela, C., Finol, C.; Mayoral, J.A.; Jaime, C. Can. J. Chem. 1987, 65, 2182.
6. Jung, M.E.; Choi, Y.M. J. Org. Chem. 1991, 56, 6729.
7. Dave, P.R.; Duddu, R.; Li, J.; Surapaneni, R.; Gilardi, R. Tetrahedron Lett. 1998, 39, 5481.
8. General procedure for the Diels-Alder reactions of 1: To a solution of 1 (1 mmol) in toluene in an Ace screw cap pressure tube was added the diene (1.1 mmol) and the resulting solution was heated in an oil bath maintained at 110 °C for 2 hours. The reaction mixture was allowed to cool and then concentrated under reduced pressure to give a residue that was purified by column chromatography on silica gel eluting with ethyl acetate/hexane (4:2).
9. 3): δ 32.42, 43.06, 46.38, 49.09, 51.29, 68.65, 124.30, 128.30, 133.34, 136.54, 144.40, 156.72.
10. Parrick, J.; Mehta, L. Other fused azetidines, azetines, and azetes. In Comprehensive Heterocyclic Chemistry II, Katritzky, A.R. Ed., Pergamon, New York 1996, 659.