Diels-Alder reactions of pyridinone o-quinodimethanes generated from substituted sulfolene[3,4-c]pyridin-4(1H)-ones

Tetrahedron

Volumn 59, Issue 29, 2003, Pages 5481-5494

  Govaerts, Tom C ^a   Vogels, Ilse A ^a   Compernolle, Frans ^a   Hoornaert, Georges J ^a  

^a UNIVERSITY OF LEUVEN   (Belgium)

Author keywords

Diels Alder reaction; ortho quinodimethane; Pyridinone

Indexed keywords

1 BENZYL 3 BROMOMETHYL 2(1H) PYRAZINONE; 3,4 DIMETHYLENE 2(1H) PYRAZINONE; PYRAZINE DERIVATIVE; PYRIDINE DERIVATIVE; PYRIDONE DERIVATIVE; UNCLASSIFIED DRUG; [3,4 C]SULFOLENE PYRIDINONE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; DIELS ALDER REACTION; PRIORITY JOURNAL;

BETULACEAE;

EID: 0038383703     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)00826-3     Document Type: Article

References (34)

1. For recent reviews, see: Collier S.J., Storr R.C. Gribble G.W., Gilchrist T.L. Progress In Heterocyclic Chemistry. Vol. 10:1998;Pergamon, New York, Chou T.S. Rev. Heteroatom. Chem. 8:1993;65 Segura J.L., Martin N. Chem. Rev. 99:1999;3199.
2. For recent reviews, see: Collier S.J., Storr R.C. Gribble G.W., Gilchrist T.L. Progress In Heterocyclic Chemistry. Vol. 10:1998;Pergamon, New York, Chou T.S. Rev. Heteroatom. Chem. 8:1993;65 Segura J.L., Martin N. Chem. Rev. 99:1999;3199.
3. For recent reviews, see: Collier S.J., Storr R.C. Gribble G.W., Gilchrist T.L. Progress In Heterocyclic Chemistry. Vol. 10:1998;Pergamon, New York, Chou T.S. Rev. Heteroatom. Chem. 8:1993;65 Segura J.L., Martin N. Chem. Rev. 99:1999;3199.
4. Herrera A., Martinez R., Gonzales B., Illescas B., Martin N., Seoane C. Tetrahedron Lett. 38:1997;4873 Chou T.S., Ko C.W. Tetrahedron. 36:1994;10721 Mertzanos G.R., Stephanidou-Stephanatou J., Tsoleris C.A., Alexandrou N.E. Tetrahedron Lett. 33:1992;8101 Shepherd M.K. J. Chem. Soc., Perkin Trans. 1. 1986;1495 Carly P.R., Cappelle S.L., Compernolle F., Hoornaert G.J. Tetrahedron. 52:1996;11889.
5. Herrera A., Martinez R., Gonzales B., Illescas B., Martin N., Seoane C. Tetrahedron Lett. 38:1997;4873 Chou T.S., Ko C.W. Tetrahedron. 36:1994;10721 Mertzanos G.R., Stephanidou-Stephanatou J., Tsoleris C.A., Alexandrou N.E. Tetrahedron Lett. 33:1992;8101 Shepherd M.K. J. Chem. Soc., Perkin Trans. 1. 1986;1495 Carly P.R., Cappelle S.L., Compernolle F., Hoornaert G.J. Tetrahedron. 52:1996;11889.
6. Herrera A., Martinez R., Gonzales B., Illescas B., Martin N., Seoane C. Tetrahedron Lett. 38:1997;4873 Chou T.S., Ko C.W. Tetrahedron. 36:1994;10721 Mertzanos G.R., Stephanidou-Stephanatou J., Tsoleris C.A., Alexandrou N.E. Tetrahedron Lett. 33:1992;8101 Shepherd M.K. J. Chem. Soc., Perkin Trans. 1. 1986;1495 Carly P.R., Cappelle S.L., Compernolle F., Hoornaert G.J. Tetrahedron. 52:1996;11889.
7. Herrera A., Martinez R., Gonzales B., Illescas B., Martin N., Seoane C. Tetrahedron Lett. 38:1997;4873 Chou T.S., Ko C.W. Tetrahedron. 36:1994;10721 Mertzanos G.R., Stephanidou-Stephanatou J., Tsoleris C.A., Alexandrou N.E. Tetrahedron Lett. 33:1992;8101 Shepherd M.K. J. Chem. Soc., Perkin Trans. 1. 1986;1495 Carly P.R., Cappelle S.L., Compernolle F., Hoornaert G.J. Tetrahedron. 52:1996;11889.
8. Herrera A., Martinez R., Gonzales B., Illescas B., Martin N., Seoane C. Tetrahedron Lett. 38:1997;4873 Chou T.S., Ko C.W. Tetrahedron. 36:1994;10721 Mertzanos G.R., Stephanidou-Stephanatou J., Tsoleris C.A., Alexandrou N.E. Tetrahedron Lett. 33:1992;8101 Shepherd M.K. J. Chem. Soc., Perkin Trans. 1. 1986;1495 Carly P.R., Cappelle S.L., Compernolle F., Hoornaert G.J. Tetrahedron. 52:1996;11889.
9. (a) Crew A.P.A., Jenkins G., Storr R.C., Yelland M. Tetrahedron Lett. 31:1990;1491 (b) Chaloner L.M., Crew A.P.A., O'Neill P.M., Storr R.C., Yelland M. Tetrahedron. 48:1992;8101 (c) Chou T.S., Chang R.C. Tetrahedron Lett. 33:1992;8121 (d) Chou T.S., Chang R.C. J. Chem. Soc., Chem. Commun. 1992;549 (e) Chou T.S., Tsai C.Y. J. Chem. Soc., Chem. Commun. 1991;1287 (f) Chou T.S., Tsai C.Y. Heterocycles. 1992;663 (g) Tomé A.C., Cavalairo J.A.S., Storr R.C. Tetrahedron. 52:1996;1723 (h) Tomé A.C., Cavalairo J.A.S., Storr R.C. Tetrahedron. 52:1996;1735 (i) Carly P.R., Govaerts T.C., Cappelle S.L., Compernolle F., Hoornaert G.J. Tetrahedron. 57:2001;4203 (j) Cappelle S.L., Vogels I., Van Meervelt L., Compernolle F., Hoornaert G.J. Tetrahedron Lett. 42:2001;3759.
10. (a) Crew A.P.A., Jenkins G., Storr R.C., Yelland M. Tetrahedron Lett. 31:1990;1491 (b) Chaloner L.M., Crew A.P.A., O'Neill P.M., Storr R.C., Yelland M. Tetrahedron. 48:1992;8101 (c) Chou T.S., Chang R.C. Tetrahedron Lett. 33:1992;8121 (d) Chou T.S., Chang R.C. J. Chem. Soc., Chem. Commun. 1992;549 (e) Chou T.S., Tsai C.Y. J. Chem. Soc., Chem. Commun. 1991;1287 (f) Chou T.S., Tsai C.Y. Heterocycles. 1992;663 (g) Tomé A.C., Cavalairo J.A.S., Storr R.C. Tetrahedron. 52:1996;1723 (h) Tomé A.C., Cavalairo J.A.S., Storr R.C. Tetrahedron. 52:1996;1735 (i) Carly P.R., Govaerts T.C., Cappelle S.L., Compernolle F., Hoornaert G.J. Tetrahedron. 57:2001;4203 (j) Cappelle S.L., Vogels I., Van Meervelt L., Compernolle F., Hoornaert G.J. Tetrahedron Lett. 42:2001;3759.
11. (a) Crew A.P.A., Jenkins G., Storr R.C., Yelland M. Tetrahedron Lett. 31:1990;1491 (b) Chaloner L.M., Crew A.P.A., O'Neill P.M., Storr R.C., Yelland M. Tetrahedron. 48:1992;8101 (c) Chou T.S., Chang R.C. Tetrahedron Lett. 33:1992;8121 (d) Chou T.S., Chang R.C. J. Chem. Soc., Chem. Commun. 1992;549 (e) Chou T.S., Tsai C.Y. J. Chem. Soc., Chem. Commun. 1991;1287 (f) Chou T.S., Tsai C.Y. Heterocycles. 1992;663 (g) Tomé A.C., Cavalairo J.A.S., Storr R.C. Tetrahedron. 52:1996;1723 (h) Tomé A.C., Cavalairo J.A.S., Storr R.C. Tetrahedron. 52:1996;1735 (i) Carly P.R., Govaerts T.C., Cappelle S.L., Compernolle F., Hoornaert G.J. Tetrahedron. 57:2001;4203 (j) Cappelle S.L., Vogels I., Van Meervelt L., Compernolle F., Hoornaert G.J. Tetrahedron Lett. 42:2001;3759.
12. (a) Crew A.P.A., Jenkins G., Storr R.C., Yelland M. Tetrahedron Lett. 31:1990;1491 (b) Chaloner L.M., Crew A.P.A., O'Neill P.M., Storr R.C., Yelland M. Tetrahedron. 48:1992;8101 (c) Chou T.S., Chang R.C. Tetrahedron Lett. 33:1992;8121 (d) Chou T.S., Chang R.C. J. Chem. Soc., Chem. Commun. 1992;549 (e) Chou T.S., Tsai C.Y. J. Chem. Soc., Chem. Commun. 1991;1287 (f) Chou T.S., Tsai C.Y. Heterocycles. 1992;663 (g) Tomé A.C., Cavalairo J.A.S., Storr R.C. Tetrahedron. 52:1996;1723 (h) Tomé A.C., Cavalairo J.A.S., Storr R.C. Tetrahedron. 52:1996;1735 (i) Carly P.R., Govaerts T.C., Cappelle S.L., Compernolle F., Hoornaert G.J. Tetrahedron. 57:2001;4203 (j) Cappelle S.L., Vogels I., Van Meervelt L., Compernolle F., Hoornaert G.J. Tetrahedron Lett. 42:2001;3759.
13. (a) Crew A.P.A., Jenkins G., Storr R.C., Yelland M. Tetrahedron Lett. 31:1990;1491 (b) Chaloner L.M., Crew A.P.A., O'Neill P.M., Storr R.C., Yelland M. Tetrahedron. 48:1992;8101 (c) Chou T.S., Chang R.C. Tetrahedron Lett. 33:1992;8121 (d) Chou T.S., Chang R.C. J. Chem. Soc., Chem. Commun. 1992;549 (e) Chou T.S., Tsai C.Y. J. Chem. Soc., Chem. Commun. 1991;1287 (f) Chou T.S., Tsai C.Y. Heterocycles. 1992;663 (g) Tomé A.C., Cavalairo J.A.S., Storr R.C. Tetrahedron. 52:1996;1723 (h) Tomé A.C., Cavalairo J.A.S., Storr R.C. Tetrahedron. 52:1996;1735 (i) Carly P.R., Govaerts T.C., Cappelle S.L., Compernolle F., Hoornaert G.J. Tetrahedron. 57:2001;4203 (j) Cappelle S.L., Vogels I., Van Meervelt L., Compernolle F., Hoornaert G.J. Tetrahedron Lett. 42:2001;3759.
14. (a) Crew A.P.A., Jenkins G., Storr R.C., Yelland M. Tetrahedron Lett. 31:1990;1491 (b) Chaloner L.M., Crew A.P.A., O'Neill P.M., Storr R.C., Yelland M. Tetrahedron. 48:1992;8101 (c) Chou T.S., Chang R.C. Tetrahedron Lett. 33:1992;8121 (d) Chou T.S., Chang R.C. J. Chem. Soc., Chem. Commun. 1992;549 (e) Chou T.S., Tsai C.Y. J. Chem. Soc., Chem. Commun. 1991;1287 (f) Chou T.S., Tsai C.Y. Heterocycles. 1992;663 (g) Tomé A.C., Cavalairo J.A.S., Storr R.C. Tetrahedron. 52:1996;1723 (h) Tomé A.C., Cavalairo J.A.S., Storr R.C. Tetrahedron. 52:1996;1735 (i) Carly P.R., Govaerts T.C., Cappelle S.L., Compernolle F., Hoornaert G.J. Tetrahedron. 57:2001;4203 (j) Cappelle S.L., Vogels I., Van Meervelt L., Compernolle F., Hoornaert G.J. Tetrahedron Lett. 42:2001;3759.
15. (a) Crew A.P.A., Jenkins G., Storr R.C., Yelland M. Tetrahedron Lett. 31:1990;1491 (b) Chaloner L.M., Crew A.P.A., O'Neill P.M., Storr R.C., Yelland M. Tetrahedron. 48:1992;8101 (c) Chou T.S., Chang R.C. Tetrahedron Lett. 33:1992;8121 (d) Chou T.S., Chang R.C. J. Chem. Soc., Chem. Commun. 1992;549 (e) Chou T.S., Tsai C.Y. J. Chem. Soc., Chem. Commun. 1991;1287 (f) Chou T.S., Tsai C.Y. Heterocycles. 1992;663 (g) Tomé A.C., Cavalairo J.A.S., Storr R.C. Tetrahedron. 52:1996;1723 (h) Tomé A.C., Cavalairo J.A.S., Storr R.C. Tetrahedron. 52:1996;1735 (i) Carly P.R., Govaerts T.C., Cappelle S.L., Compernolle F., Hoornaert G.J. Tetrahedron. 57:2001;4203 (j) Cappelle S.L., Vogels I., Van Meervelt L., Compernolle F., Hoornaert G.J. Tetrahedron Lett. 42:2001;3759.
16. (a) Crew A.P.A., Jenkins G., Storr R.C., Yelland M. Tetrahedron Lett. 31:1990;1491 (b) Chaloner L.M., Crew A.P.A., O'Neill P.M., Storr R.C., Yelland M. Tetrahedron. 48:1992;8101 (c) Chou T.S., Chang R.C. Tetrahedron Lett. 33:1992;8121 (d) Chou T.S., Chang R.C. J. Chem. Soc., Chem. Commun. 1992;549 (e) Chou T.S., Tsai C.Y. J. Chem. Soc., Chem. Commun. 1991;1287 (f) Chou T.S., Tsai C.Y. Heterocycles. 1992;663 (g) Tomé A.C., Cavalairo J.A.S., Storr R.C. Tetrahedron. 52:1996;1723 (h) Tomé A.C., Cavalairo J.A.S., Storr R.C. Tetrahedron. 52:1996;1735 (i) Carly P.R., Govaerts T.C., Cappelle S.L., Compernolle F., Hoornaert G.J. Tetrahedron. 57:2001;4203 (j) Cappelle S.L., Vogels I., Van Meervelt L., Compernolle F., Hoornaert G.J. Tetrahedron Lett. 42:2001;3759.
17. (a) Crew A.P.A., Jenkins G., Storr R.C., Yelland M. Tetrahedron Lett. 31:1990;1491 (b) Chaloner L.M., Crew A.P.A., O'Neill P.M., Storr R.C., Yelland M. Tetrahedron. 48:1992;8101 (c) Chou T.S., Chang R.C. Tetrahedron Lett. 33:1992;8121 (d) Chou T.S., Chang R.C. J. Chem. Soc., Chem. Commun. 1992;549 (e) Chou T.S., Tsai C.Y. J. Chem. Soc., Chem. Commun. 1991;1287 (f) Chou T.S., Tsai C.Y. Heterocycles. 1992;663 (g) Tomé A.C., Cavalairo J.A.S., Storr R.C. Tetrahedron. 52:1996;1723 (h) Tomé A.C., Cavalairo J.A.S., Storr R.C. Tetrahedron. 52:1996;1735 (i) Carly P.R., Govaerts T.C., Cappelle S.L., Compernolle F., Hoornaert G.J. Tetrahedron. 57:2001;4203 (j) Cappelle S.L., Vogels I., Van Meervelt L., Compernolle F., Hoornaert G.J. Tetrahedron Lett. 42:2001;3759.
18. (a) Crew A.P.A., Jenkins G., Storr R.C., Yelland M. Tetrahedron Lett. 31:1990;1491 (b) Chaloner L.M., Crew A.P.A., O'Neill P.M., Storr R.C., Yelland M. Tetrahedron. 48:1992;8101 (c) Chou T.S., Chang R.C. Tetrahedron Lett. 33:1992;8121 (d) Chou T.S., Chang R.C. J. Chem. Soc., Chem. Commun. 1992;549 (e) Chou T.S., Tsai C.Y. J. Chem. Soc., Chem. Commun. 1991;1287 (f) Chou T.S., Tsai C.Y. Heterocycles. 1992;663 (g) Tomé A.C., Cavalairo J.A.S., Storr R.C. Tetrahedron. 52:1996;1723 (h) Tomé A.C., Cavalairo J.A.S., Storr R.C. Tetrahedron. 52:1996;1735 (i) Carly P.R., Govaerts T.C., Cappelle S.L., Compernolle F., Hoornaert G.J. Tetrahedron. 57:2001;4203 (j) Cappelle S.L., Vogels I., Van Meervelt L., Compernolle F., Hoornaert G.J. Tetrahedron Lett. 42:2001;3759.
19. Govaerts T.C., Vogels I., Compernolle F., Hoornaert G.J. Tetrahedron Lett. 43:2002;799-802.
20. (a) Dolle V., Nguyen C.H., Legraverend M., Aubertin A.M., Kirn A., Andreola M.L., Ventura M., Tarrago-Litvak L., Bisagni E. J. Med. Chem. 43:2000;3949-3962 (b) Fink D.M., Bores G.M., Effland R.C., Huger F.P., Kurys B.E., Rush D.K., Selk D.E. J. Med. Chem. 38:2000;3645-3651.
21. (a) Dolle V., Nguyen C.H., Legraverend M., Aubertin A.M., Kirn A., Andreola M.L., Ventura M., Tarrago-Litvak L., Bisagni E. J. Med. Chem. 43:2000;3949-3962 (b) Fink D.M., Bores G.M., Effland R.C., Huger F.P., Kurys B.E., Rush D.K., Selk D.E. J. Med. Chem. 38:2000;3645-3651.
22. Buysens K.J., Vandenberghe D.M., Toppet S.M., Hoornaert G.J. Tetrahedron. 51:1995;12463-12478.
23. Buysens K.J., Vandenberghe D.M., Hoornaert G.J. Tetrahedron. 52:1996;9161-9178.
24. See Ref. 3(j).
25. (a) Ciganek E. Org. React. 32:1984;1 (b) Ciganek E., Schubert E.M. J. Org. Chem. 60:1995;4629-4634 (c) Ghelfi F., Parsons A.F., Tommasini D., Mucci A., Eur. J. Org. Chem. 2001;1845-1852 (d) Padwa A., Reger T.S. Can. J. Chem. 78:2000;749-756.
26. (a) Ciganek E. Org. React. 32:1984;1 (b) Ciganek E., Schubert E.M. J. Org. Chem. 60:1995;4629-4634 (c) Ghelfi F., Parsons A.F., Tommasini D., Mucci A., Eur. J. Org. Chem. 2001;1845-1852 (d) Padwa A., Reger T.S. Can. J. Chem. 78:2000;749-756.
27. (a) Ciganek E. Org. React. 32:1984;1 (b) Ciganek E., Schubert E.M. J. Org. Chem. 60:1995;4629-4634 (c) Ghelfi F., Parsons A.F., Tommasini D., Mucci A., Eur. J. Org. Chem. 2001;1845-1852 (d) Padwa A., Reger T.S. Can. J. Chem. 78:2000;749-756.
28. (a) Ciganek E. Org. React. 32:1984;1 (b) Ciganek E., Schubert E.M. J. Org. Chem. 60:1995;4629-4634 (c) Ghelfi F., Parsons A.F., Tommasini D., Mucci A., Eur. J. Org. Chem. 2001;1845-1852 (d) Padwa A., Reger T.S. Can. J. Chem. 78:2000;749-756.
29. (a) Junge H., Oehme G. Tetrahedron. 54:1998;11027-11032 (b) Li W.T., Lai F.C., Lee G.H., Peng S.M., Liu R.S. J. Am. Chem. Soc. 120:1998;4520-4521 (c) Hoornaert G.J. Bull. Soc. Chim. Belg. 103:1994;583-589.
30. (a) Junge H., Oehme G. Tetrahedron. 54:1998;11027-11032 (b) Li W.T., Lai F.C., Lee G.H., Peng S.M., Liu R.S. J. Am. Chem. Soc. 120:1998;4520-4521 (c) Hoornaert G.J. Bull. Soc. Chim. Belg. 103:1994;583-589.
31. (a) Junge H., Oehme G. Tetrahedron. 54:1998;11027-11032 (b) Li W.T., Lai F.C., Lee G.H., Peng S.M., Liu R.S. J. Am. Chem. Soc. 120:1998;4520-4521 (c) Hoornaert G.J. Bull. Soc. Chim. Belg. 103:1994;583-589.
32. (a) Shepherd M.K. J. Chem. Soc. Perkin Trans. 1. 1986;1495-1496 (b) Cappelle S.L., Vogels I.A., Govaerts T.C., Toppet S.M., Compernolle F., Hoornaert G.J. Tetrahedron. 58:2002;3655-3666 (c) Jefford C.W., Bernardinelli G., Wang Y., Spellmeyer D.C., Buda A., Houk K.N. J. Am. Chem. Soc. 114:1992;1157-1165.
33. (a) Shepherd M.K. J. Chem. Soc. Perkin Trans. 1. 1986;1495-1496 (b) Cappelle S.L., Vogels I.A., Govaerts T.C., Toppet S.M., Compernolle F., Hoornaert G.J. Tetrahedron. 58:2002;3655-3666 (c) Jefford C.W., Bernardinelli G., Wang Y., Spellmeyer D.C., Buda A., Houk K.N. J. Am. Chem. Soc. 114:1992;1157-1165.
34. (a) Shepherd M.K. J. Chem. Soc. Perkin Trans. 1. 1986;1495-1496 (b) Cappelle S.L., Vogels I.A., Govaerts T.C., Toppet S.M., Compernolle F., Hoornaert G.J. Tetrahedron. 58:2002;3655-3666 (c) Jefford C.W., Bernardinelli G., Wang Y., Spellmeyer D.C., Buda A., Houk K.N. J. Am. Chem. Soc. 114:1992;1157-1165.