The Use of 4-Hetaryliden- and 4-Aryliden-5(4H)-oxazolones as Dienophiles. Appropriate Reagents for the Synthesis of Cyclic Analogues of Natural Amino Acids

Journal of Heterocyclic Chemistry

Volumn 34, Issue 4, 1997, Pages 1099-1110

  Avenoza, A ^a   Busto, J H ^a   Paris M ^a   Peregrina, J M ^a   Cativiela, C ^b  

^a UNIVERSITY OF LA RIOJA   (Spain)

^b UNIVERSITY OF ZARAGOZA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001245684     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570340402     Document Type: Article

References (38)

1. J. W. Cornforth, in Chemistry of Penicillin. H. T. Clarke and J. R. Johnson, eds, Princeton, New Jersey, 1949, pp 688-848.
2. Y. S. Rao and R. Filler, Oxazolones, I. J. Turchi, ed, The Chemistry of Heterocyclic Compounds, A Series of Monographs, A. Weissberger, and E. C. Taylor, eds, John Wiley and Sons, New York, 1986, pp 363-691; A. K. Mukerjee and P. Kumar, Heterocycles, 16, 1995 (1985); A. K. Mukerjee, Heterocycles, 26, 1077 (1987).
3. Y. S. Rao and R. Filler, Oxazolones, I. J. Turchi, ed, The Chemistry of Heterocyclic Compounds, A Series of Monographs, A. Weissberger, and E. C. Taylor, eds, John Wiley and Sons, New York, 1986, pp 363-691; A. K. Mukerjee and P. Kumar, Heterocycles, 16, 1995 (1985); A. K. Mukerjee, Heterocycles, 26, 1077 (1987).
4. Y. S. Rao and R. Filler, Oxazolones, I. J. Turchi, ed, The Chemistry of Heterocyclic Compounds, A Series of Monographs, A. Weissberger, and E. C. Taylor, eds, John Wiley and Sons, New York, 1986, pp 363-691; A. K. Mukerjee and P. Kumar, Heterocycles, 16, 1995 (1985); A. K. Mukerjee, Heterocycles, 26, 1077 (1987).
5. S. W. King, J. M. Riordan, E. M. Holt and C. H. Stammer, J. Org. Chem., 47, 3270 (1982); M. Suzuki, S. D. Kumar and C. H. Stammer, J. Org. Chem., 48, 4769 (1983); I. Arenal, M. Bernabé, E. Fernández-Alvarez, M. L. Izquierdo and S. Penodes, J. Heterocyclic Chem., 20, 607 (1983); C. Cativiela, M. D. Díaz de Villegas, J. A. Mayoral and E. Meléndez, J. Org. Chem., 49, 1436 (1984); C. Cativiela, M. D. Díaz de Villegas and E. Meléndez, J. Heterocyclic Chem., 22, 1655 (1985); N. G. Argyropoulus and E. Coutouli-Argyropoulus, J. Heterocyclic Chem., 21, 1397 (1984).
6. S. W. King, J. M. Riordan, E. M. Holt and C. H. Stammer, J. Org. Chem., 47, 3270 (1982); M. Suzuki, S. D. Kumar and C. H. Stammer, J. Org. Chem., 48, 4769 (1983); I. Arenal, M. Bernabé, E. Fernández-Alvarez, M. L. Izquierdo and S. Penodes, J. Heterocyclic Chem., 20, 607 (1983); C. Cativiela, M. D. Díaz de Villegas, J. A. Mayoral and E. Meléndez, J. Org. Chem., 49, 1436 (1984); C. Cativiela, M. D. Díaz de Villegas and E. Meléndez, J. Heterocyclic Chem., 22, 1655 (1985); N. G. Argyropoulus and E. Coutouli-Argyropoulus, J. Heterocyclic Chem., 21, 1397 (1984).
7. S. W. King, J. M. Riordan, E. M. Holt and C. H. Stammer, J. Org. Chem., 47, 3270 (1982); M. Suzuki, S. D. Kumar and C. H. Stammer, J. Org. Chem., 48, 4769 (1983); I. Arenal, M. Bernabé, E. Fernández-Alvarez, M. L. Izquierdo and S. Penodes, J. Heterocyclic Chem., 20, 607 (1983); C. Cativiela, M. D. Díaz de Villegas, J. A. Mayoral and E. Meléndez, J. Org. Chem., 49, 1436 (1984); C. Cativiela, M. D. Díaz de Villegas and E. Meléndez, J. Heterocyclic Chem., 22, 1655 (1985); N. G. Argyropoulus and E. Coutouli-Argyropoulus, J. Heterocyclic Chem., 21, 1397 (1984).
8. S. W. King, J. M. Riordan, E. M. Holt and C. H. Stammer, J. Org. Chem., 47, 3270 (1982); M. Suzuki, S. D. Kumar and C. H. Stammer, J. Org. Chem., 48, 4769 (1983); I. Arenal, M. Bernabé, E. Fernández-Alvarez, M. L. Izquierdo and S. Penodes, J. Heterocyclic Chem., 20, 607 (1983); C. Cativiela, M. D. Díaz de Villegas, J. A. Mayoral and E. Meléndez, J. Org. Chem., 49, 1436 (1984); C. Cativiela, M. D. Díaz de Villegas and E. Meléndez, J. Heterocyclic Chem., 22, 1655 (1985); N. G. Argyropoulus and E. Coutouli-Argyropoulus, J. Heterocyclic Chem., 21, 1397 (1984).
9. S. W. King, J. M. Riordan, E. M. Holt and C. H. Stammer, J. Org. Chem., 47, 3270 (1982); M. Suzuki, S. D. Kumar and C. H. Stammer, J. Org. Chem., 48, 4769 (1983); I. Arenal, M. Bernabé, E. Fernández-Alvarez, M. L. Izquierdo and S. Penodes, J. Heterocyclic Chem., 20, 607 (1983); C. Cativiela, M. D. Díaz de Villegas, J. A. Mayoral and E. Meléndez, J. Org. Chem., 49, 1436 (1984); C. Cativiela, M. D. Díaz de Villegas and E. Meléndez, J. Heterocyclic Chem., 22, 1655 (1985); N. G. Argyropoulus and E. Coutouli-Argyropoulus, J. Heterocyclic Chem., 21, 1397 (1984).
10. S. W. King, J. M. Riordan, E. M. Holt and C. H. Stammer, J. Org. Chem., 47, 3270 (1982); M. Suzuki, S. D. Kumar and C. H. Stammer, J. Org. Chem., 48, 4769 (1983); I. Arenal, M. Bernabé, E. Fernández-Alvarez, M. L. Izquierdo and S. Penodes, J. Heterocyclic Chem., 20, 607 (1983); C. Cativiela, M. D. Díaz de Villegas, J. A. Mayoral and E. Meléndez, J. Org. Chem., 49, 1436 (1984); C. Cativiela, M. D. Díaz de Villegas and E. Meléndez, J. Heterocyclic Chem., 22, 1655 (1985); N. G. Argyropoulus and E. Coutouli-Argyropoulus, J. Heterocyclic Chem., 21, 1397 (1984).
11. C. Cativiela, J. A. Mayoral, A. Avenoza, M. González and M. A. Roy, Synthesis, 114 (1990).
12. C. Cativiela, M. D. Díaz-de-Villegas, J. A. Mayoral, A. Avenoza and J. M. Peregrina, Tetrahedron, 49, 677 (1993).
13. C. Cativiela, M. D. Díaz-de-Villegas, A. Avenoza and J. M. Peregrina, Tetrahedron, 49, 10987 (1993).
14. C. Cativiela, A. Avenoza, J. H. Busto and J. M. Peregrina, Tetrahedron, 50, 12989 (1994).
15. J. Plöchl, Ber., 16, 2815, (1883); H. E. Carter, Org. React., 3, 198, (1946).
16. J. Plöchl, Ber., 16, 2815, (1883); H. E. Carter, Org. React., 3, 198, (1946).
17. D. Rideout and R. Breslow J. Am. Chem. Soc., 102, 7816 (1980); R. Breslow, U. Maitra and D. Rideout, Tetrahedron Letters, 24, 1901 (1983); R. Breslow and U. Maitra, Tetrahedron Letters, 25, 1239 (1984); S. Larsen and P. Grieco, J. Am. Chem. Soc., 107, 1768 (1985); P. Grieco, P. Galastis and R. Spohn, Tetrahedron, 42, 2847 (1986); A. Lubineau and Y. Queneau, Tetrahedron Letters, 26, 2653 (1985); H. Schneider and N. Sangwan, J. Chem. Soc., Chem. Commun., 1787 (1986); C. Cativiela, A. Avenoza, J. A. Mayoral, J. M. Peregrina and M. A. Roy, J. Phys. Org. Chem., 3, 414 (1990); C. Cativiela, A. Avenoza, J. A. Mayoral, J. I. García, J. M. Peregrina and M. A. Roy, J. Phys. Org. Chem., 4, 48 (1991).
18. D. Rideout and R. Breslow J. Am. Chem. Soc., 102, 7816 (1980); R. Breslow, U. Maitra and D. Rideout, Tetrahedron Letters, 24, 1901 (1983); R. Breslow and U. Maitra, Tetrahedron Letters, 25, 1239 (1984); S. Larsen and P. Grieco, J. Am. Chem. Soc., 107, 1768 (1985); P. Grieco, P. Galastis and R. Spohn, Tetrahedron, 42, 2847 (1986); A. Lubineau and Y. Queneau, Tetrahedron Letters, 26, 2653 (1985); H. Schneider and N. Sangwan, J. Chem. Soc., Chem. Commun., 1787 (1986); C. Cativiela, A. Avenoza, J. A. Mayoral, J. M. Peregrina and M. A. Roy, J. Phys. Org. Chem., 3, 414 (1990); C. Cativiela, A. Avenoza, J. A. Mayoral, J. I. García, J. M. Peregrina and M. A. Roy, J. Phys. Org. Chem., 4, 48 (1991).
19. D. Rideout and R. Breslow J. Am. Chem. Soc., 102, 7816 (1980); R. Breslow, U. Maitra and D. Rideout, Tetrahedron Letters, 24, 1901 (1983); R. Breslow and U. Maitra, Tetrahedron Letters, 25, 1239 (1984); S. Larsen and P. Grieco, J. Am. Chem. Soc., 107, 1768 (1985); P. Grieco, P. Galastis and R. Spohn, Tetrahedron, 42, 2847 (1986); A. Lubineau and Y. Queneau, Tetrahedron Letters, 26, 2653 (1985); H. Schneider and N. Sangwan, J. Chem. Soc., Chem. Commun., 1787 (1986); C. Cativiela, A. Avenoza, J. A. Mayoral, J. M. Peregrina and M. A. Roy, J. Phys. Org. Chem., 3, 414 (1990); C. Cativiela, A. Avenoza, J. A. Mayoral, J. I. García, J. M. Peregrina and M. A. Roy, J. Phys. Org. Chem., 4, 48 (1991).
20. D. Rideout and R. Breslow J. Am. Chem. Soc., 102, 7816 (1980); R. Breslow, U. Maitra and D. Rideout, Tetrahedron Letters, 24, 1901 (1983); R. Breslow and U. Maitra, Tetrahedron Letters, 25, 1239 (1984); S. Larsen and P. Grieco, J. Am. Chem. Soc., 107, 1768 (1985); P. Grieco, P. Galastis and R. Spohn, Tetrahedron, 42, 2847 (1986); A. Lubineau and Y. Queneau, Tetrahedron Letters, 26, 2653 (1985); H. Schneider and N. Sangwan, J. Chem. Soc., Chem. Commun., 1787 (1986); C. Cativiela, A. Avenoza, J. A. Mayoral, J. M. Peregrina and M. A. Roy, J. Phys. Org. Chem., 3, 414 (1990); C. Cativiela, A. Avenoza, J. A. Mayoral, J. I. García, J. M. Peregrina and M. A. Roy, J. Phys. Org. Chem., 4, 48 (1991).
21. D. Rideout and R. Breslow J. Am. Chem. Soc., 102, 7816 (1980); R. Breslow, U. Maitra and D. Rideout, Tetrahedron Letters, 24, 1901 (1983); R. Breslow and U. Maitra, Tetrahedron Letters, 25, 1239 (1984); S. Larsen and P. Grieco, J. Am. Chem. Soc., 107, 1768 (1985); P. Grieco, P. Galastis and R. Spohn, Tetrahedron, 42, 2847 (1986); A. Lubineau and Y. Queneau, Tetrahedron Letters, 26, 2653 (1985); H. Schneider and N. Sangwan, J. Chem. Soc., Chem. Commun., 1787 (1986); C. Cativiela, A. Avenoza, J. A. Mayoral, J. M. Peregrina and M. A. Roy, J. Phys. Org. Chem., 3, 414 (1990); C. Cativiela, A. Avenoza, J. A. Mayoral, J. I. García, J. M. Peregrina and M. A. Roy, J. Phys. Org. Chem., 4, 48 (1991).
22. D. Rideout and R. Breslow J. Am. Chem. Soc., 102, 7816 (1980); R. Breslow, U. Maitra and D. Rideout, Tetrahedron Letters, 24, 1901 (1983); R. Breslow and U. Maitra, Tetrahedron Letters, 25, 1239 (1984); S. Larsen and P. Grieco, J. Am. Chem. Soc., 107, 1768 (1985); P. Grieco, P. Galastis and R. Spohn, Tetrahedron, 42, 2847 (1986); A. Lubineau and Y. Queneau, Tetrahedron Letters, 26, 2653 (1985); H. Schneider and N. Sangwan, J. Chem. Soc., Chem. Commun., 1787 (1986); C. Cativiela, A. Avenoza, J. A. Mayoral, J. M. Peregrina and M. A. Roy, J. Phys. Org. Chem., 3, 414 (1990); C. Cativiela, A. Avenoza, J. A. Mayoral, J. I. García, J. M. Peregrina and M. A. Roy, J. Phys. Org. Chem., 4, 48 (1991).
23. D. Rideout and R. Breslow J. Am. Chem. Soc., 102, 7816 (1980); R. Breslow, U. Maitra and D. Rideout, Tetrahedron Letters, 24, 1901 (1983); R. Breslow and U. Maitra, Tetrahedron Letters, 25, 1239 (1984); S. Larsen and P. Grieco, J. Am. Chem. Soc., 107, 1768 (1985); P. Grieco, P. Galastis and R. Spohn, Tetrahedron, 42, 2847 (1986); A. Lubineau and Y. Queneau, Tetrahedron Letters, 26, 2653 (1985); H. Schneider and N. Sangwan, J. Chem. Soc., Chem. Commun., 1787 (1986); C. Cativiela, A. Avenoza, J. A. Mayoral, J. M. Peregrina and M. A. Roy, J. Phys. Org. Chem., 3, 414 (1990); C. Cativiela, A. Avenoza, J. A. Mayoral, J. I. García, J. M. Peregrina and M. A. Roy, J. Phys. Org. Chem., 4, 48 (1991).
24. D. Rideout and R. Breslow J. Am. Chem. Soc., 102, 7816 (1980); R. Breslow, U. Maitra and D. Rideout, Tetrahedron Letters, 24, 1901 (1983); R. Breslow and U. Maitra, Tetrahedron Letters, 25, 1239 (1984); S. Larsen and P. Grieco, J. Am. Chem. Soc., 107, 1768 (1985); P. Grieco, P. Galastis and R. Spohn, Tetrahedron, 42, 2847 (1986); A. Lubineau and Y. Queneau, Tetrahedron Letters, 26, 2653 (1985); H. Schneider and N. Sangwan, J. Chem. Soc., Chem. Commun., 1787 (1986); C. Cativiela, A. Avenoza, J. A. Mayoral, J. M. Peregrina and M. A. Roy, J. Phys. Org. Chem., 3, 414 (1990); C. Cativiela, A. Avenoza, J. A. Mayoral, J. I. García, J. M. Peregrina and M. A. Roy, J. Phys. Org. Chem., 4, 48 (1991).
25. D. Rideout and R. Breslow J. Am. Chem. Soc., 102, 7816 (1980); R. Breslow, U. Maitra and D. Rideout, Tetrahedron Letters, 24, 1901 (1983); R. Breslow and U. Maitra, Tetrahedron Letters, 25, 1239 (1984); S. Larsen and P. Grieco, J. Am. Chem. Soc., 107, 1768 (1985); P. Grieco, P. Galastis and R. Spohn, Tetrahedron, 42, 2847 (1986); A. Lubineau and Y. Queneau, Tetrahedron Letters, 26, 2653 (1985); H. Schneider and N. Sangwan, J. Chem. Soc., Chem. Commun., 1787 (1986); C. Cativiela, A. Avenoza, J. A. Mayoral, J. M. Peregrina and M. A. Roy, J. Phys. Org. Chem., 3, 414 (1990); C. Cativiela, A. Avenoza, J. A. Mayoral, J. I. García, J. M. Peregrina and M. A. Roy, J. Phys. Org. Chem., 4, 48 (1991).
26. 5e). For endo/exo ratio of cycloadducts 6 and 7, see Experimental.
27. F. M. F. Chern and N. L. Benoiton, Can. J. Chem., 55, 1433 (1977); H. Muxfeldtand and W. Rogalski, J. Am. Chem. Soc., 87, 933 (1965); H. Meerwein, G. Hinz, P. Hofmann, E. Kroning and E. Pfeil, J. Prakt. Chem., 147, 257 (1936).
28. F. M. F. Chern and N. L. Benoiton, Can. J. Chem., 55, 1433 (1977); H. Muxfeldtand and W. Rogalski, J. Am. Chem. Soc., 87, 933 (1965); H. Meerwein, G. Hinz, P. Hofmann, E. Kroning and E. Pfeil, J. Prakt. Chem., 147, 257 (1936).
29. F. M. F. Chern and N. L. Benoiton, Can. J. Chem., 55, 1433 (1977); H. Muxfeldtand and W. Rogalski, J. Am. Chem. Soc., 87, 933 (1965); H. Meerwein, G. Hinz, P. Hofmann, E. Kroning and E. Pfeil, J. Prakt. Chem., 147, 257 (1936).
30. J. H. Burckhalter and G. Schmied, J. Pharm. Sci., 55, 443 (1966).
31. F. Fringelli and A. Taticchi, Dienes in the Diels-Alder Reaction, John Wiley and Sons, Inc. New York, 1990.
32. P. N. Rylander, Hydrogenation Methods, A. R. Katritzky, O. Meth-Cohn and C. W. Rees, eds, Best Synthetic Methods, Academic Press. London. 1985; P. Beak and T. L. Chaffin, J. Org. Chem., 35, 2275 (1970); J. E. McMurry, Tetrahedron Letters, 3731 (1970); R. G. Powel, R. V. Madrigal, C. R. Smith Jr. and K. L. Mikolajczak, J. Org. Chem., 39, 676 (1974); E. J. Warawa and J. R. Campbell, J. Org. Chem., 39, 3511 (1974); M. J. Gula and T. A. Spencer, J. Org. Chem., 45, 805 (1980); B. Bosnich and M. D. Fryzuk, Top. Stereochem., 12, 119 (1981).
33. P. N. Rylander, Hydrogenation Methods, A. R. Katritzky, O. Meth-Cohn and C. W. Rees, eds, Best Synthetic Methods, Academic Press. London. 1985; P. Beak and T. L. Chaffin, J. Org. Chem., 35, 2275 (1970); J. E. McMurry, Tetrahedron Letters, 3731 (1970); R. G. Powel, R. V. Madrigal, C. R. Smith Jr. and K. L. Mikolajczak, J. Org. Chem., 39, 676 (1974); E. J. Warawa and J. R. Campbell, J. Org. Chem., 39, 3511 (1974); M. J. Gula and T. A. Spencer, J. Org. Chem., 45, 805 (1980); B. Bosnich and M. D. Fryzuk, Top. Stereochem., 12, 119 (1981).
34. P. N. Rylander, Hydrogenation Methods, A. R. Katritzky, O. Meth-Cohn and C. W. Rees, eds, Best Synthetic Methods, Academic Press. London. 1985; P. Beak and T. L. Chaffin, J. Org. Chem., 35, 2275 (1970); J. E. McMurry, Tetrahedron Letters, 3731 (1970); R. G. Powel, R. V. Madrigal, C. R. Smith Jr. and K. L. Mikolajczak, J. Org. Chem., 39, 676 (1974); E. J. Warawa and J. R. Campbell, J. Org. Chem., 39, 3511 (1974); M. J. Gula and T. A. Spencer, J. Org. Chem., 45, 805 (1980); B. Bosnich and M. D. Fryzuk, Top. Stereochem., 12, 119 (1981).
35. P. N. Rylander, Hydrogenation Methods, A. R. Katritzky, O. Meth-Cohn and C. W. Rees, eds, Best Synthetic Methods, Academic Press. London. 1985; P. Beak and T. L. Chaffin, J. Org. Chem., 35, 2275 (1970); J. E. McMurry, Tetrahedron Letters, 3731 (1970); R. G. Powel, R. V. Madrigal, C. R. Smith Jr. and K. L. Mikolajczak, J. Org. Chem., 39, 676 (1974); E. J. Warawa and J. R. Campbell, J. Org. Chem., 39, 3511 (1974); M. J. Gula and T. A. Spencer, J. Org. Chem., 45, 805 (1980); B. Bosnich and M. D. Fryzuk, Top. Stereochem., 12, 119 (1981).
36. P. N. Rylander, Hydrogenation Methods, A. R. Katritzky, O. Meth-Cohn and C. W. Rees, eds, Best Synthetic Methods, Academic Press. London. 1985; P. Beak and T. L. Chaffin, J. Org. Chem., 35, 2275 (1970); J. E. McMurry, Tetrahedron Letters, 3731 (1970); R. G. Powel, R. V. Madrigal, C. R. Smith Jr. and K. L. Mikolajczak, J. Org. Chem., 39, 676 (1974); E. J. Warawa and J. R. Campbell, J. Org. Chem., 39, 3511 (1974); M. J. Gula and T. A. Spencer, J. Org. Chem., 45, 805 (1980); B. Bosnich and M. D. Fryzuk, Top. Stereochem., 12, 119 (1981).
37. P. N. Rylander, Hydrogenation Methods, A. R. Katritzky, O. Meth-Cohn and C. W. Rees, eds, Best Synthetic Methods, Academic Press. London. 1985; P. Beak and T. L. Chaffin, J. Org. Chem., 35, 2275 (1970); J. E. McMurry, Tetrahedron Letters, 3731 (1970); R. G. Powel, R. V. Madrigal, C. R. Smith Jr. and K. L. Mikolajczak, J. Org. Chem., 39, 676 (1974); E. J. Warawa and J. R. Campbell, J. Org. Chem., 39, 3511 (1974); M. J. Gula and T. A. Spencer, J. Org. Chem., 45, 805 (1980); B. Bosnich and M. D. Fryzuk, Top. Stereochem., 12, 119 (1981).
38. P. N. Rylander, Hydrogenation Methods, A. R. Katritzky, O. Meth-Cohn and C. W. Rees, eds, Best Synthetic Methods, Academic Press. London. 1985; P. Beak and T. L. Chaffin, J. Org. Chem., 35, 2275 (1970); J. E. McMurry, Tetrahedron Letters, 3731 (1970); R. G. Powel, R. V. Madrigal, C. R. Smith Jr. and K. L. Mikolajczak, J. Org. Chem., 39, 676 (1974); E. J. Warawa and J. R. Campbell, J. Org. Chem., 39, 3511 (1974); M. J. Gula and T. A. Spencer, J. Org. Chem., 45, 805 (1980); B. Bosnich and M. D. Fryzuk, Top. Stereochem., 12, 119 (1981).