Regio- and stereoselective intramolecular Heck reactions of N-acyl-2,3-dihydro-4-pyridones

Tetrahedron Letters

Volumn 37, Issue 6, 1996, Pages 793-796

  Comins, Daniel L ^a   Joseph, Sajan P ^a   Zhang, Yue Mei ^a  

^a NORTH CAROLINA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PYRIDINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030058096     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02297-X     Document Type: Article

References (28)

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2. (b) Comins, D. L.; Killpack, M. O. J. Am. Chem. Soc. 1992, 114, 10972.
3. (c) Comins, D. L.; Chung, G.; Foley, M. A. Heterocycles 1994, 37, 1121 and references cited therein.
4. For reviews covering the addition of organometallics to 1-acylpyridinium salts, see: (a) Comins, D. L.; O'Connor, S. Adv. Heterocycl. Chem. 1988, 44, 199.;
5. (b) Comins, D. L.; Joseph, S. P. Advances in Nitrogen Heterocycles: Moody, C. J., Ed.; JAI Press: Greenwich, Vol. 2, in press.
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11. Comins, D. L.; LaMunyon, D. H. J. Org. Chem. 1992, 57, 5807 and references cited therein.
12. Comins, D. L.; Radi Benjelloun, N. Tetrahedron Lett. 1994, 35, 829.
13. (a) Comins, D. L.; Dehghani, A. J. Chem. Soc., Chem. Commun. 1993, 1838.
14. (b) Comins, D. L.; Dehghani, A. J. Org. Chem. 1995, 60, 794.
15. Beckwith, A. L. J.; Joseph, S. P.; Mayadunne, R. T. A. J. Org. Chem. 1993, 58, 4198.
16. For recent reviews on the Heck reaction, see: de Meijere, A.; Meyer, F. E. Angew. Chem. Int. Ed. Engl. 1994, 33, 2379.; Grigg, R. J. Heterocyclic Chem. 1994, 31, 631. Hegedus, L. S. in Organometallics in Synthesis ; Schlosser M., Ed.; Wiley, Chichester, 1994, 383. Heck, R. F. in Comprehensive Organic Synthesis ; Trost, B. M. ; Fleming, I., Eds.; 1991, Vol 4, 833.
17. For recent reviews on the Heck reaction, see: de Meijere, A.; Meyer, F. E. Angew. Chem. Int. Ed. Engl. 1994, 33, 2379.; Grigg, R. J. Heterocyclic Chem. 1994, 31, 631. Hegedus, L. S. in Organometallics in Synthesis ; Schlosser M., Ed.; Wiley, Chichester, 1994, 383. Heck, R. F. in Comprehensive Organic Synthesis ; Trost, B. M. ; Fleming, I., Eds.; 1991, Vol 4, 833.
18. For recent reviews on the Heck reaction, see: de Meijere, A.; Meyer, F. E. Angew. Chem. Int. Ed. Engl. 1994, 33, 2379.; Grigg, R. J. Heterocyclic Chem. 1994, 31, 631. Hegedus, L. S. in Organometallics in Synthesis ; Schlosser M., Ed.; Wiley, Chichester, 1994, 383. Heck, R. F. in Comprehensive Organic Synthesis ; Trost, B. M. ; Fleming, I., Eds.; 1991, Vol 4, 833.
19. For recent reviews on the Heck reaction, see: de Meijere, A.; Meyer, F. E. Angew. Chem. Int. Ed. Engl. 1994, 33, 2379.; Grigg, R. J. Heterocyclic Chem. 1994, 31, 631. Hegedus, L. S. in Organometallics in Synthesis ; Schlosser M., Ed.; Wiley, Chichester, 1994, 383. Heck, R. F. in Comprehensive Organic Synthesis ; Trost, B. M. ; Fleming, I., Eds.; 1991, Vol 4, 833.
20. For intramolecular Heck reactions of tetrahydropyridines, see: Grigg, R.; Sridharan, V.; Stevenson, P.; Sukirthalingam, S.; Worakun, T. Tetrahedron 1990, 46, 4003.
21. In a typical experiment, a mixture of the substrate (1 mmol), triethylamine (4 mmol), formic acid (4 mmol) and DMF (5 mL) were heated at 80 °C for 6 to 15 h. In some cases better yields of the products were obtained by replacing triethylamine and formic acid with tetrabutylammonium bromide and sodium formate (1 eq).
22. Hoffman, R. W. Chem. Rev. 1989, 89, 1841.; Johnson, F. Chem. Rev. 1968, 68, 375.; Foley, M. A.: Comins, D. L. J. Am. Chem. Soc. 1988, 110, 7445 and references cited therein.
23. Hoffman, R. W. Chem. Rev. 1989, 89, 1841.; Johnson, F. Chem. Rev. 1968, 68, 375.; Foley, M. A.: Comins, D. L. J. Am. Chem. Soc. 1988, 110, 7445 and references cited therein.
24. Hoffman, R. W. Chem. Rev. 1989, 89, 1841.; Johnson, F. Chem. Rev. 1968, 68, 375.; Foley, M. A.: Comins, D. L. J. Am. Chem. Soc. 1988, 110, 7445 and references cited therein.
25. For recent work on intramolecular Pd-catalyzed aryl-enone conjugate additions, see: Friestad, G. K.; Branchaud, B. P. Tetrahedron Lett. 1995, 36, 7047 and references cited therein.
26. The relative stereochemistry was determined by comparing the coupling constants with theoretical values obtained from PC-MODEL (Serena Software).
27. Samsel, E. G.; Norton, J. R. J. Am. Chem. Soc. 1984, 106, 5505.; Thorn, D. L.; Hoffmann, R. J. Am. Chem. Soc. 1978, 100, 2079.
28. Samsel, E. G.; Norton, J. R. J. Am. Chem. Soc. 1984, 106, 5505.; Thorn, D. L.; Hoffmann, R. J. Am. Chem. Soc. 1978, 100, 2079.