Non-biomimetic oxidation of 1,4-dihydropyridines

Chemical Communications

Volumn , Issue 2, 1997, Pages 213-214

  Lavilla, Rodolfo ^a   Gullón, Francisco ^a   Barón, Xavier ^a   Bosch, Joan ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001003164     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a606919c     Document Type: Article

References (29)

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2. For reviews on the chemistry of dihydropyridines, see: U. Eisner and J. Kuthan, Chem. Rev., 1972, 72, 1; D. M. Stout and A. I. Meyers, Chem. Rev., 1982, 82, 223.
3. R. Lavilla, T. Gotsens, M. Guerrero and J. Bosch. Synthesis, 1995, 382 and references cited therein.
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11. L. A. Negievich, O. M. Grishin and A. A. Yasnikov, Ukr. Khim. Zh., 1968, 34 684 (Chem. Abstr., 1969, 70, 11513); L. A. Negievich, O. M. Grishin and A. A. Yasnikov, Ukr. Khim. Zh. 1968, 34, 802 (Chem. Abstr., 1969, 70, 28776).
12. L. A. Negievich, O. M. Grishin and A. A. Yasnikov, Ukr. Khim. Zh., 1968, 34 684 (Chem. Abstr., 1969, 70, 11513); L. A. Negievich, O. M. Grishin and A. A. Yasnikov, Ukr. Khim. Zh. 1968, 34, 802 (Chem. Abstr., 1969, 70, 28776).
13. L. A. Negievich, O. M. Grishin and A. A. Yasnikov, Ukr. Khim. Zh., 1968, 34 684 (Chem. Abstr., 1969, 70, 11513); L. A. Negievich, O. M. Grishin and A. A. Yasnikov, Ukr. Khim. Zh. 1968, 34, 802 (Chem. Abstr., 1969, 70, 28776).
14. For a 4 + 2 cycloaddilion involving N-acyl-1,2-dihydropyridines and singlet oxygen, see: M. Natsume, Y. Sekine, M. Ogawa, H. Soyagimi and Y. Kitagawa, Tetrahedron Lett., 1979, 3476; for the osmylation of N-acyl-1,2-dihydropyndines, see: T. Tschamber, F. Backenstrass, M. Neuburger, M. Zehnder and J. Streith, Tetrahedron, 1994, 50, 1135.
15. For a 4 + 2 cycloaddilion involving N-acyl-1,2-dihydropyridines and singlet oxygen, see: M. Natsume, Y. Sekine, M. Ogawa, H. Soyagimi and Y. Kitagawa, Tetrahedron Lett., 1979, 3476; for the osmylation of N-acyl-1,2-dihydropyndines, see: T. Tschamber, F. Backenstrass, M. Neuburger, M. Zehnder and J. Streith, Tetrahedron, 1994, 50, 1135.
16. J. K. Crandall, in Encyclopedia of Reagents for Organic Synthesis, ed. L. A. Paquette, Wiley. Chichester, 1995, vol. 3, p. 2061; W. Adam, R. Curei and J. O. Edwards, Acc. Chem. Res., 1989, 22, 205; R. W. Murray, Chem. Rev., 1989, 89, 1187.
17. J. K. Crandall, in Encyclopedia of Reagents for Organic Synthesis, ed. L. A. Paquette, Wiley. Chichester, 1995, vol. 3, p. 2061; W. Adam, R. Curei and J. O. Edwards, Acc. Chem. Res., 1989, 22, 205; R. W. Murray, Chem. Rev., 1989, 89, 1187.
18. J. K. Crandall, in Encyclopedia of Reagents for Organic Synthesis, ed. L. A. Paquette, Wiley. Chichester, 1995, vol. 3, p. 2061; W. Adam, R. Curei and J. O. Edwards, Acc. Chem. Res., 1989, 22, 205; R. W. Murray, Chem. Rev., 1989, 89, 1187.
19. W. Adam, E.-M. Peters, K. Peters, H.-G. von Schnering and V. Voerckel. Chem. Ber., 1992, 125, 1263; W. Adam, M. Ahrweiler, K. Paulini, H.-U. Reissig and V. Voerckel. Chem. Ber., 1992, 125, 2719; L. E. Burgess, E. K.M. Gross and J. Jurka. Tetrahedron Lett., 1996, 37, 3255.
20. W. Adam, E.-M. Peters, K. Peters, H.-G. von Schnering and V. Voerckel. Chem. Ber., 1992, 125, 1263; W. Adam, M. Ahrweiler, K. Paulini, H.-U. Reissig and V. Voerckel. Chem. Ber., 1992, 125, 2719; L. E. Burgess, E. K.M. Gross and J. Jurka. Tetrahedron Lett., 1996, 37, 3255.
21. W. Adam, E.-M. Peters, K. Peters, H.-G. von Schnering and V. Voerckel. Chem. Ber., 1992, 125, 1263; W. Adam, M. Ahrweiler, K. Paulini, H.-U. Reissig and V. Voerckel. Chem. Ber., 1992, 125, 2719; L. E. Burgess, E. K.M. Gross and J. Jurka. Tetrahedron Lett., 1996, 37, 3255.
22. W, Adam, M. Heil and R. Hutterer, J. Org. Chem., 1992, 57, 4491.
23. M. E. Brewster, A. Simay, K. Czako, D. Winwood, H. Farag and N. Bodor, J. Org. Chem., 1989, 54, 3721.
24. D. Yang, M.-K. Wong and Y.-C. Yip, J. Org. Chem., 1995, 60, 3887.
25. For related structures, see: B. Koppenhoefer, W. Winter and E. Bayer, Liebigs Ann. Chem., 1983, 1986; W. Adam, K. Peters and M. Sauter, Synthesis, 1994, 111; C. Agami, F. Couty, L. Hamon, B. Prince and C. Pnchot, Tetrahedron, 1990, 46, 7003; W. Adam, D. Reinhardt, H.-U. Reissig and K. Paulini, Tetrahedron, 1995, 51, 12257.
26. For related structures, see: B. Koppenhoefer, W. Winter and E. Bayer, Liebigs Ann. Chem., 1983, 1986; W. Adam, K. Peters and M. Sauter, Synthesis, 1994, 111; C. Agami, F. Couty, L. Hamon, B. Prince and C. Pnchot, Tetrahedron, 1990, 46, 7003; W. Adam, D. Reinhardt, H.-U. Reissig and K. Paulini, Tetrahedron, 1995, 51, 12257.
27. For related structures, see: B. Koppenhoefer, W. Winter and E. Bayer, Liebigs Ann. Chem., 1983, 1986; W. Adam, K. Peters and M. Sauter, Synthesis, 1994, 111; C. Agami, F. Couty, L. Hamon, B. Prince and C. Pnchot, Tetrahedron, 1990, 46, 7003; W. Adam, D. Reinhardt, H.-U. Reissig and K. Paulini, Tetrahedron, 1995, 51, 12257.
28. For related structures, see: B. Koppenhoefer, W. Winter and E. Bayer, Liebigs Ann. Chem., 1983, 1986; W. Adam, K. Peters and M. Sauter, Synthesis, 1994, 111; C. Agami, F. Couty, L. Hamon, B. Prince and C. Pnchot, Tetrahedron, 1990, 46, 7003; W. Adam, D. Reinhardt, H.-U. Reissig and K. Paulini, Tetrahedron, 1995, 51, 12257.
29. DMD solutions were prepared according to W. Adam, J. Bialas and L. Hadjiarapoglou, Chem. Ber., 1991, 124, 2377, and the dioxirane content (ca 0.07 M) was determined by iodometric titration.