Intramolecular cyclizations of N-acyliminium ions with pyridine rings

Arkivoc

Volumn 2002, Issue 6, 2002, Pages 35-48

  Padwa, Albert ^a   Brodney, Michael A ^a  

^a EMORY UNIVERSITY   (United States)

Author keywords

Intramolecular cyclizations; N acyliminium ions; Pyridines; Regiochemical

Indexed keywords

1 [2 (6 METHOXYPYRIDIN 2 YL)ETHYL]PYRROLIDINE 2,5 DIONE; 10 [2 (6 METHOXYPYRIDIN 2 YL)ETHYL] 3,7,7 TRIMETHYL 9 OXO 11 OXA 10 AZATRICYCLO[6.2.1.0 1,6 ]UNDECANE 8 CARBOXYLIC ACID ETHYL ESTER; 10 [2 (6 METHOXYPYRIDIN 2 YL)ETHYL] 9 OXO 11 OXA 10 AZATRICYCLO[6.2.1.0 1,6 ]UNDECANE 8 CARBOXYLIC ACID ETHYL ESTER; 2 (2 METHOXYPYRIDIN 4 YL)ETHANOL; 2 (6 METHOXYPYRIDIN 2 YL)ETHANOL; 2 (6 METHOXYPYRIDIN 2 YL)ETHYLAMINE; 2 [2 (2 METHOXYPYRIDIN 4 YL)ETHYL]ISOINDOLE 1,3 DIONE; 2 [2 (6 METHOXYPYRIDIN 2 YL)ETHYL]ISOINDOLE 1,3 DIONE; 2 DIAZO N HEPT 6 ENOYL N [2 (6 METHOXYPYRIDIN 2 YL)ETHYL]MALONAMIC ACID ETHYL ESTER; 3 ETHOXY 2 [2 (6 METHOXYPYRIDIN 2 YL)ETHYL] 2,3 DIHYDROISOINDOL 1 ONE; 3 HYDROXY 1 [2 (6 METHOXYPYRIDIN 2 YL)ETHYL]OXO 1,2,3,4,5,6,7,8 OCTAHYDROQUINOLINE 3 CARBOXYLIC ACID ETHYL ESTER; 3 HYDROXY 2 [2 (2 METHOXYPYRIDIN 4 YL)ETHYL] 2,3 DIHYDROISOINDOL 1 ONE; 3 HYDROXY 2 [2 (6 METHOXYPYRIDIN 2 YL)ETHYL] 2,3 DIHYDROISOINDOL 1 ONE; 3 METHOXY 5,9,10,10A TETRAHYDRO 6H PYRROLO[2,1 F][1,6]NAPHTHYRIDIN 8 ONE; 3,7 DIMETHYLOCT 6 ENOIC ACID [2 (6 METHOXYPYRIDIN 2 YL)ETHYL]AMIDE; 5 HYDROXY 1 [2 (6 METHOXYPYRIDIN 2 YL)ETHYL]PYRROLIDIN 2 ONE; HEPT 6 ENOIC ACID [2 (6 METHOXYPYRIDIN 2 YL)ETHYL]AMIDE; IMINE; ION; N (3,7 DIMETHYLOCT 6 ENOYL) N [2 (6 METHOXYPYRIDIN 2 YL)ETHYL]MALONAMIC ACID ETHYL ESTER; N HEPT 6 ENOYL N [2 (6 METHYOXYPYRIDIN 2 YL)ETHYL]MALONAMIC ACID ETHYL ESTER; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; SYNTHESIS;

EID: 3242814647     PISSN: 14246376     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (40)

1. Mondon, A.; Hansen, K. F.; Boehme, K.; Faro, H. P.; Nestler, H. J.; Vilhuber, H. G.; Böttcher, K. Chem. Ber. 1970, 103, 615. Mondon, A.; Seidel, P. R. Chem. Ber. 1971, 104, 2937. Mondon, A.; Nestler, H. J. Chem. Ber. 1979, 112, 1329.
2. Mondon, A.; Hansen, K. F.; Boehme, K.; Faro, H. P.; Nestler, H. J.; Vilhuber, H. G.; Böttcher, K. Chem. Ber. 1970, 103, 615. Mondon, A.; Seidel, P. R. Chem. Ber. 1971, 104, 2937. Mondon, A.; Nestler, H. J. Chem. Ber. 1979, 112, 1329.
3. Mondon, A.; Hansen, K. F.; Boehme, K.; Faro, H. P.; Nestler, H. J.; Vilhuber, H. G.; Böttcher, K. Chem. Ber. 1970, 103, 615. Mondon, A.; Seidel, P. R. Chem. Ber. 1971, 104, 2937. Mondon, A.; Nestler, H. J. Chem. Ber. 1979, 112, 1329.
4. Hiemstra, H.; Speckamp, W. N. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I, Eds.; Pergamon: Oxford, 1991; Vol. 2, pp 1047-1082.
5. Kametani, T.; Fukumoto, K. The Chemistry of Heterocyclic Compounds, Isoquinoline Part One; Grethe, G., Ed.; Wiley, New York; pp 170-182. Jones, G. Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W. Eds. Pergamon: Oxford, 1984; vol. 2, pp 438-440. Padwa, A.; Brodney, M. A.; Marino, J. P.; Sheehan, S. M. J. Org. Chem. 1997, 62, 78.
6. Kametani, T.; Fukumoto, K. The Chemistry of Heterocyclic Compounds, Isoquinoline Part One; Grethe, G., Ed.; Wiley, New York; pp 170-182. Jones, G. Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W. Eds. Pergamon: Oxford, 1984; vol. 2, pp 438-440. Padwa, A.; Brodney, M. A.; Marino, J. P.; Sheehan, S. M. J. Org. Chem. 1997, 62, 78.
7. Kametani, T.; Fukumoto, K. The Chemistry of Heterocyclic Compounds, Isoquinoline Part One; Grethe, G., Ed.; Wiley, New York; pp 170-182. Jones, G. Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W. Eds. Pergamon: Oxford, 1984; vol. 2, pp 438-440. Padwa, A.; Brodney, M. A.; Marino, J. P.; Sheehan, S. M. J. Org. Chem. 1997, 62, 78.
8. Speckamp, W.N. Recl. Trav. Chim. Pays Bas. 1981, 100, 345. Veenstra, S.J.; Speckamp, W.N. J. Am. Chem. Soc. 1981, 103. 4645. Wijnberg, B.P.; Speckamp, W.N. Tetrahedron Lett. 1981, 22, 5079.
9. Speckamp, W.N. Recl. Trav. Chim. Pays Bas. 1981, 100, 345. Veenstra, S.J.; Speckamp, W.N. J. Am. Chem. Soc. 1981, 103. 4645. Wijnberg, B.P.; Speckamp, W.N. Tetrahedron Lett. 1981, 22, 5079.
10. Speckamp, W.N. Recl. Trav. Chim. Pays Bas. 1981, 100, 345. Veenstra, S.J.; Speckamp, W.N. J. Am. Chem. Soc. 1981, 103. 4645. Wijnberg, B.P.; Speckamp, W.N. Tetrahedron Lett. 1981, 22, 5079.
11. Hart, D.J. J. Org. Chem. 1981, 46, 367. Hart, D.J. J. Org. Chem. 1981, 46, 3576. Hart, D.J.; Kanai, K. J. Org. Chem. 1982, 47, 1555. Hart, D.J.; Yang, T.K. Tetrahedron Lett. 1982, 23, 2671. Hart, D.J.; Kanai, K. J. Am. Chem. Soc. 1983, 105, 1255.
12. Hart, D.J. J. Org. Chem. 1981, 46, 367. Hart, D.J. J. Org. Chem. 1981, 46, 3576. Hart, D.J.; Kanai, K. J. Org. Chem. 1982, 47, 1555. Hart, D.J.; Yang, T.K. Tetrahedron Lett. 1982, 23, 2671. Hart, D.J.; Kanai, K. J. Am. Chem. Soc. 1983, 105, 1255.
13. Hart, D.J. J. Org. Chem. 1981, 46, 367. Hart, D.J. J. Org. Chem. 1981, 46, 3576. Hart, D.J.; Kanai, K. J. Org. Chem. 1982, 47, 1555. Hart, D.J.; Yang, T.K. Tetrahedron Lett. 1982, 23, 2671. Hart, D.J.; Kanai, K. J. Am. Chem. Soc. 1983, 105, 1255.
14. Hart, D.J. J. Org. Chem. 1981, 46, 367. Hart, D.J. J. Org. Chem. 1981, 46, 3576. Hart, D.J.; Kanai, K. J. Org. Chem. 1982, 47, 1555. Hart, D.J.; Yang, T.K. Tetrahedron Lett. 1982, 23, 2671. Hart, D.J.; Kanai, K. J. Am. Chem. Soc. 1983, 105, 1255.
15. Hart, D.J. J. Org. Chem. 1981, 46, 367. Hart, D.J. J. Org. Chem. 1981, 46, 3576. Hart, D.J.; Kanai, K. J. Org. Chem. 1982, 47, 1555. Hart, D.J.; Yang, T.K. Tetrahedron Lett. 1982, 23, 2671. Hart, D.J.; Kanai, K. J. Am. Chem. Soc. 1983, 105, 1255.
16. Whaley, W.H.; Govindachari, T.R. Org. React. Wiley: New York, 1951, pp 151-206.
17. Langkopf, E.; Schinzer, D. Chem. Rev. 1995, 95, 1375. Hong, C.Y.; Kado, N.; Overman, L.E. J. Am. Chem. Soc. 1993, 115, 11028. Ofial, A.R.; Mayr, H. J. Org. Chem. 1996, 61, 5823.
18. Langkopf, E.; Schinzer, D. Chem. Rev. 1995, 95, 1375. Hong, C.Y.; Kado, N.; Overman, L.E. J. Am. Chem. Soc. 1993, 115, 11028. Ofial, A.R.; Mayr, H. J. Org. Chem. 1996, 61, 5823.
19. Langkopf, E.; Schinzer, D. Chem. Rev. 1995, 95, 1375. Hong, C.Y.; Kado, N.; Overman, L.E. J. Am. Chem. Soc. 1993, 115, 11028. Ofial, A.R.; Mayr, H. J. Org. Chem. 1996, 61, 5823.
20. Franklin, A.S.; Overman, L.E. Chem. Rev. 1996, 96, 505. Blumankopf, T.A.; Overman, L.E. Chem. Rev. 1996, 86, 857.
21. Franklin, A.S.; Overman, L.E. Chem. Rev. 1996, 96, 505. Blumankopf, T.A.; Overman, L.E. Chem. Rev. 1996, 86, 857.
22. Reviews: (a) Gellert, E. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S.W., Ed.; John Wiley and Sons; New York, NY, 1987; Vol. 5.
23. (b) Suffness, M.; Cordell, G.A. in The Alkaloids; Brossi, A., Ed.; Academic Press, Orlando, FL, 198. Vol. 25, p 156.
24. (c) Bick, R.C.; Sinchai, W. in The Alkaloids; Rodrigo, R.G.A., Ed.; Academic Press: New York, 1981; Vol. 19, p 193.
25. (d) Govindachari, T.R. in The Alkaloids; Manske, R.H.F., Ed.; Academic Press: New York, 1967; Vol. 9, p 517.
26. Reviews: (a) Pyridine and its Derivatives, Supplemental ed., Abramovitch, R.A. Wiley-Interscience, New York, 1974.
27. (b) Smith, D.M. in Comprehensive Organic Chemistry Vol. 4, Ed. Sammes, P.G., Pergamon, Oxford, 1979.
28. (c) Heterocyclic Chemistry, Gilchrist, T. L. Pitman Publ. Ltd.: London, 1985.
29. Comins, D.L.; Joseph, S.P. in Comprehensive Heterocyclic Chemistry 2, Ed. Mckillop, A. Elsevier Science Ltd., Oxford, 1996.
30. Gray, M. A.; Konopski, L.; Langlois, Y. Synthetic Commun. 1994, 24, 1367.
31. Mitsunobu, O. Synthesis, 1981, 1.
32. Fisher, M. L.; Overman, L. E. J. Org. Chem. 1990, 55, 1447.
33. Osterhout, M. H.; Nadler, W. R.; Padwa, A. Synthesis 1994, 123.
34. Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223.
35. Padwa, A.; Hertzog, D. L.; Nadler, W. R. J. Org. Chem. 1994, 59,7072.
36. Padwa, A.; Brodney, M. A.; Marino, J. P. Jr.; Osterhout, M. H.; Price, A. T. J. Org. Chem. 1997, 62, 67.
37. Padwa, A.; Brodney, M. A.; Marino, J. P. Jr.; Sheehan, S. M. J. Org. Chem. 1997, 62, 78.
38. Sato, M.; Kanuma, N.; Kato, T. Chem. Pharm. Bull. 1982, 30, 1315. Regitz, M.; Hocker, J.; Leidhergener, A. Org. Synth.; John Wiley: New York, 1973; Collect. Vol. 5, p 179.
39. Sato, M.; Kanuma, N.; Kato, T. Chem. Pharm. Bull. 1982, 30, 1315. Regitz, M.; Hocker, J.; Leidhergener, A. Org. Synth.; John Wiley: New York, 1973; Collect. Vol. 5, p 179.
40. Adger, B. M.; Ayrey, P.; Bannister, R.; Forth, M. A.; Hajikarimian, Y.; Lewis, N. J. J. Chem. Soc., Perkin Trans. I 1988, 2791.