Synthesis of 2,4-disubstituted N-acyl-5,6-dihydro-2-pyridones

Tetrahedron Letters

Volumn 37, Issue 52, 1996, Pages 9275-9278

  Comins, Daniel L ^a   Chen, Xinghai ^a   Joseph, Sajan P ^a  

^a NORTH CAROLINA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PYRIDONE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS;

EID: 0030599666     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)82940-1     Document Type: Article

References (18)

1. 1. (a) Comins, D. L.; Joseph, S. P.; Goehring, R. R. J. Am. Chem. Soc. 1994, 116, 4719.
2. (b) Comins, D. L.; Dehghani, A. J. Org. Chem. 1995, 60, 794 and references cited therein.
3. 2. Comins, D. L.; Joseph, S. P. In Advances in Nitrogen Heterocydes; Moody, C. J., ed.; JAI Press, Inc.: Greenwich, Vol. 2, pp. 251-294.
4. 3. The synthetic utility of C-6 unsubstituted N-acyl-5,6-dihydro-2-pyridones has been demonstrated. For leading references, see: (a) Torisawa, Y.; Nakagawa, M.; Arai, H.; Lai, Z.; Hino, T.; Nakata, T.; Oishi, T. Tetrahedron Lett.. 1990, 31, 3195.
5. (b) Torisawa, Y.; Nakagawa, M.; Hosaka, T.; Tanabe, K.; Lai, Z.; Ogata, K.; Nakata, T.; Oishi, T.; Hino, T. J. Org. Chem. 1992, 57, 5741.
6. 4. Organocerium reagents undergo efficient carbonyl addition, see: (a) Imamoto, T. Pure Appl. Chem. 1990, 62, 747 and references cited therein.
7. (b) Comins, D. L.; Hong, H.; Saha, J.; Jianhua, G. J. Org. Chem. 1994, 59, 5120.
8. (c) Hong, H.; Comins, D. L. J. Org. Chem. 1995, 61, 391.
9. 5. For leading references on the oxidative rearrangement of tertiary allylic alcohols, see: Luzzio, F. A.; Moore, W. J. J. Org. Chem. 1993, 58, 2966.
10. 6. Guziec, F. S., Jr.; Luzzio, F. A. Synthesis 1980, 691. The BPCC used in this study was purchased from the Aldrich Chemical Company.
11. 7. An alkylative carbonyl transposition of dihydro-γ-pyrones to a to a α, β-unsaturated δ-lactones has been reported, see: Nangia, A.; Rao, P. B. Tetrahedron Lett. 1993, 34, 2681.
12. 8. Gilman, H.; Lichtenwalter, G. D. J. Am. Chem. Soc. 1958, 80, 608.
13. 9. Fleming, I.; Dunoqués, J.; Smithers, R. Org. React. 1989, 39, 57-575.
14. 10. The enantiomeric purity of 2e was determined by HPLC using a chiralcel OJ column (J.T. Baker, Inc., Phillipsburg, NJ).
15. 11. All new compounds were spectroscopically characterized and furnished satisfactory elemental analyses (C, H, N ± 0.4%) or high-resolution mass spectra.
16. 12. (a) Comins, D. L.; Salvador, J. M. Tetrahedron Lett. 1993, 34, 801.
17. (b) Comins, D. L.; Salvador, J. M. J. Org. Chem. 1993, 58, 4656.
18. (c) Comins, D. L.; Guerra-Weltzien, L. Tetrahedron Lett. 1996, 37, 3807.