Intermolecularly selective [4+4] photocycloaddition of 2-pyridone mixtures

Tetrahedron Letters

Volumn 37, Issue 8, 1996, Pages 1141-1144

  Sieburth, Scott McN ^a   Lin, Chao Hsiung ^a  

^a STONY BROOK UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 PYRIDONE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; PHOTOCHEMISTRY; REACTION ANALYSIS; STEREOCHEMISTRY; X RAY ANALYSIS;

EID: 0004597227     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02417-4     Document Type: Article

References (18)

1. See Sieburth, S. McN.; Hiel, G.; Lin, C.-H.; Kuan, D. P. J. Org. Chem. 1994, 59, 80-87. and references therein.
2. Matsushima, R.; Terada, K. J. Chem. Soc., Perkin Trans 2 1985, 1445-1448. Corey, E. J.; Streith, J. J. Am. Chem. Soc. 1964, 86, 950-951.
3. Matsushima, R.; Terada, K. J. Chem. Soc., Perkin Trans 2 1985, 1445-1448. Corey, E. J.; Streith, J. J. Am. Chem. Soc. 1964, 86, 950-951.
4. De Selms, R. C.; Schleigh, W. R. Tetrahedron Lett. 1972, 3563-3566.
5. Kaneko, C.; Shiba, K.; Fujii, H.; Momose, Y. J. Chem. Soc., Chem. Commun. 1980, 1177-1178. Kaneko, C.; Katagiri, N.; Sato, M.; Muto, M.; Sakamoto, T.; Saikawa, S.; Naito, T.; Saito, A. J. Chem. Soc., Perkin Trans. 1 1986, 1283-1288.
6. Kaneko, C.; Shiba, K.; Fujii, H.; Momose, Y. J. Chem. Soc., Chem. Commun. 1980, 1177-1178. Kaneko, C.; Katagiri, N.; Sato, M.; Muto, M.; Sakamoto, T.; Saikawa, S.; Naito, T.; Saito, A. J. Chem. Soc., Perkin Trans. 1 1986, 1283-1288.
7. K. Ravindran research notes, SUNY Stony Brook.
8. Sieburth, S. McN.; Ravindran, K. Tetrahedron Lett. 1994, 35, 3861-3864.
9. Sato, E.; Ikeda, Y.; Kanaoka, Y. Liebigs Ann. Chem. 1989, 781-788.
10. Nagano, T.; Hirobe, M.; Okamoto, T. Tetrahedron Lett. 1977, 3891-3894.
11. The yields for 9 and 10 are based on 5 as the limiting reagent. The ratio of the products is calculated as the relative molar quantities of cycloadducts products.
12. The apparent difference in the experimental details of our procedures and those of Kaneko are the use of a medium pressure mercury lamp (ours) versus a high pressure mercury lamp.
13. The calculated quantity of recovered pyridone 6 takes into account the quantity consumed in the formation of 11 as well as 13 and 14, typically 15-20% overall yields based on the amount of 5 consumed in the reaction.
14. 13C NMR, IR, MS and combustion analysis.
15. Sieburth, S. McN.; Lin, C.-H. J. Org. Chem. 1994, 59, 3597-3599.
16. w) = 0.067 (0.071).
17. Barrett, A. G. M. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Ed.; Pergamon: New York, 1991; Vol. 8; pp 235-257. Zabicky, J. The Chemistry of Amides; Interscience: New York, 1970.
18. Barrett, A. G. M. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Ed.; Pergamon: New York, 1991; Vol. 8; pp 235-257. Zabicky, J. The Chemistry of Amides; Interscience: New York, 1970.