[4+2] Cycloaddition reactions of 4-sulfur-substituted 2-pyridones with electron-deficient dienophiles

Tetrahedron

Volumn 64, Issue 22, 2008, Pages 5291-5297

  Chou, Shang Shing P ^a   Wang, Hui Chen ^a   Chen, Pong Won ^a   Yang, Chun Han ^a  

^a FU JEN CATHOLIC UNIVERSITY   (Taiwan)

Author keywords

2 Pyridones; 4+2 Cycloaddition reactions; Diels Alder reactions; Isoquinuclidines

Indexed keywords

4 (PHENYLSULFONYL) 1 TOSYL 2 PYRIDONE; 4 (PHENYLSULFONYL) 2 TOSYL 2 PYRIDINOL; 4 (PHENYLTHIO) 1 TOSYL 2 PYRIDONE; 4 (PHENYLTHIO) 2 TOSYL PYRIDINOL; ALKADIENE; ENDO 4 METHYL 10 (PHENYLSULFONYL) 8 TOSYL 4,8 DIAZA TRICYCLO[5.2.2.0 2,6]UNDEC 10 ENE 3,5,9 TRIONE; ENDO 4 METHYL 10 (PHENYLTHIO) 8 TOSYL 4,8 DIAZA TRICYCLO[5.2.2.0 2,6]UNDEC 10 ENE 3,5,9 TRIONE; ENDO 4 PHENYL 10 (PHENYLSULFONYL) 8 TOSYL 4,8 DIAZA TRICYCLO[5.2.2.0 2,6]UNDEC 10 ENE 3,5,9 TRIONE; ENDO 4 PHENYL 10 (PHENYLTHIO) 8 TOSYL 4,8 DIAZA TRICYCLO[5.2.2.0 2,6]UNDEC 10 ENE 3,5,9 TRIONE; ENDO METHYL 3 OXO 8 (PHENYLSULFONYL) 2 TOSYL 2 AZABICYCLO[2.2.2]OCT 7 ENE 6 CARBOXYLATE; ENDO METHYL 3 OXO 8 (PHNEYLTHIO) 2 TOSYL 2 AZA BICYCLO[2.2.2]OCT 7 ENE 6 CARBOXYLATE; EXO METHYL 3 OXO 8 (PHENYLSULFONYL) 2 TOSYL 2 AZABICYCLO[2.2.2]OCT 7 ENE 6 CARBOXYLATE; N BENZYL 4 (PHENYLSULFONYL) 2 PYRIDONE; N BENZYL 4 (PHENYLTHIO) 2 PYRIDONE; N METHYL 4 (PHENYLSULFONYL) 2 PYRIDONE; N METHYL 4 (PHENYLTHIO) 2 PYRIDONE; PYRIDONE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; PRIORITY JOURNAL; STEREOCHEMISTRY;

ALNUS;

EID: 42749097425     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.03.030     Document Type: Article

References (50)

1. For a recent review, see:. Torres M., Gil S., and Parra M. Curr. Org. Chem. 9 (2005) 1757-1779
2. Schultz A.G. Chem. Rev. 73 (1973) 385-405
3. Kelly T.R., Bell S.H., Ohashi N., and Armstrong-Chong R.J. J. Am. Chem. Soc. 110 (1988) 6471-6480
4. Snider B.B., and Lu Q. J. Org. Chem. 59 (1994) 8065-8070
5. Kozikowski A.P., Campiani G., Sun L.-Q., Wang S., Saxena A., and Doctor B.P. J. Am. Chem. Soc. 118 (1996) 11357-11362
6. Wall M.E. Med. Res. Rev. 18 (1998) 299-314
7. Li Q., Mitscher L.A., and Shen L.L. Med. Res. Rev. 20 (2000) 231-293
8. For a review, see:. Afarinkia K., Vinader V., Nelson T.D., and Posner G.H. Tetrahedron 48 (1992) 9111-9171
9. For the synthesis of vinblastine-type alkaloids, see:. Kuehne M.E., and Marko I. In: Brossi A., and Suffness M. (Eds). The Alkaloids. Antitumor Bisindole Alkaloids from Catharanthus roseus (L.) Vol. 37 (1990), Academic, San Diego 77-131
10. For the synthesis of ibogaine-type alkaloids, see:. Popik P., and Skolnick P. In: Cordell G.A. (Ed). The Alkaloids. Chemistry and Biology Vol. 52 (1999), Academic, San Diego 197-231
11. For the synthesis of other alkaloids, see:. Martin S.F., Rueger H., Williamson S.A., and Grzejszczak S. J. Am. Chem. Soc. 109 (1987) 6124-6134
12. Krow G.R., Cheung O.H., Hu Z., Huang Q., Hutchinson J., Liu N., Nguyen K.T., Ulrich S., Yuan J., Xiao Y., Wypij D.M., Zuo F., and Carroll P.J. Tetrahedron 55 (1999) 7747-7756
13. Paquette L.A. J. Org. Chem. 30 (1965) 2107-2108
14. Acheson M.R., and Tasker P.A. J. Chem. Soc. C (1967) 1542-1543
15. Mariano P.S., Krochmal E., Beamer R., Huesmann P.L., and Dunaway-Mariano D. Tetrahedron 34 (1978) 2609-2612
16. Tomisawa H., and Hongo H. Tetrahedron Lett. (1969) 2465-2468
17. Shusherina N.P., and Gapeeva M.V. J. Org. Chem. USSR 9 (1973) 874
18. Mariano P.S., Huesmann P.L., Beamer R.L., and Dunaway-Mariano D. Tetrahedron 34 (1978) 2617-2626
19. Tomisawa H., Hongo H., Kato H., Fujita R., and Sato A. Chem. Pharm. Bull. 26 (1978) 2312-2315
20. Tomisawa H., Hongo H., Kato H., Haraki T., and Fujita R. Chem. Pharm. Bull. 27 (1979) 670-675
21. Gompper R., and Schmidt A. Angew. Chem., Int. Ed. Engl. 19 (1980) 463-464
22. Tomisawa H., Hongo H., Kato H., Sato K., and Fujita R. Heterocycles 16 (1981) 1947-1950
23. Passarella D., Favia R., Giardini A., Lesma G., Martinelli M., Silvani A., Danieli B., Efange S.M.N., and Mash D.C. Biorog. Med. Chem. 11 (2003) 1007-1014
24. Mckillop A., Zeelesko M.-T., and Taylor E.C. Tetrahedron Lett. (1968) 4945-4948
25. McCarty C.G., and Garner L.A. In: Patai S. (Ed). Chemistry of Amidines and Imidates (1975), Wiley, New York, NY 189-240
26. Gisby G.P., Royall S.E., and Sammes P.G. J. Chem. Soc., Chem. Commun. (1979) 501-502
27. Gisby G.P., Royall S.E., and Sammes P.G. J. Chem. Soc., Perkin Trans. 1 (1982) 169-173
28. Herdeis C., and Hartke C. Synthesis (1988) 76-78
29. Herdeis C., and Hartke-Karger C. Arch. Pharm. (Weinheim, Ger.) 323 (1990) 937-942
30. Nakano H., Tomisawa H., and Hongo H. J. Chem. Soc., Chem. Commun. (1990) 1775-1776
31. Nakano H., Saito Y., and Hongo H. Chem. Pharm. Bull. 40 (1992) 2876-2878
32. Okamura H., Nagaike H., Iwagawa T., and Nakatani M. Tetrahedron Lett. 41 (2000) 8317-8321
33. Lorthiois E., Meyyappan M., and Vasella A. Chem. Commun. (2000) 1829-1830
34. Böhm M., Lorthiois E., Meyyappan M., and Vasella A. Helv. Chim. Acta 86 (2003) 3787-3817
35. Posner G.H., and Switzer C. J. Org. Chem. 52 (1987) 1642-1644
36. Posner G.H., Vinader V., and Afarinkia K. J. Org. Chem. 57 (1992) 4088-4097
37. Afarinkia K., and Mahmood F. Tetrahedron Lett. 39 (1998) 493-496
38. Tomisawa H., Nakano H., and Hongo H. Heterocycles 30 (1990) 359-362
39. Chou S.S.P., and Hung C.C. Tetrahedron Lett. 41 (2000) 8323-8326
40. Chou S.S.P., and Hung C.C. Synthesis (2001) 2450-2462
41. Chou S.S.P., Chiu H.C., and Hung C.C. Tetrahedron Lett. 44 (2003) 4653-4655
42. Chou S.S.P., and Ho C.W. Tetrahedron Lett. 46 (2005) 8551-8554
43. Chou S.S.P., Hsieh H.I., and Hung C.C. J. Chin. Chem. Soc. 53 (2006) 891-900
44. Chou S.S.P., Liang C.F., Lee T.M., and Liu C.F. Tetrahedron 63 (2007) 8267-8273
45. Chou S.S.P., and Chen P.W. Tetrahedron 64 (2008) 1879-1887
46. Hopkins P.B., and Fuchs P.L. J. Org. Chem. 43 (1978) 1208-1217
47. Gundermann K.D., and Holtman P. Angew. Chem., Int. Ed. Engl. 5 (1966) 668
48. Parsons A.F., and Pettifer R.M. Tetrahedron Lett. 37 (1996) 1667-1671
49. Crystallographic data (excluding structure factors) for the structures in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication nos. CCDC 659438 (9a), 659439 (8b), 659440 (10b). Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44 (0)1223 336033 or e-mail: deposit@ccdc.cam.ac.uk).
50. Shusherina N.P., Pilipenko V.S., Kireeva O.K., Geller B.I., and Stepanyants A.U. J. Org. Chem. USSR 16 (1980) 2047-2051