Oxidative Diphosphonylation of 1,4-Dihydropyridines and Pyridinium Salts

Organic Letters

Volumn 2, Issue 11, 2000, Pages 1533-1535

  Lavilla, Rodolfo ^a   Spada, Alessandro ^a   Bosch, Joan ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000404158     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0057380     Document Type: Article

References (32)

1. (a) Lavilla, R.; Barón, X.; Coll, O.; Gullón, F.; Masdeu, C.; Bosch, J. J. Org. Chem. 1998, 63, 10001.
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4. (d) Lavilla, R.; Kumar, R.; Coll, O.; Masdeu, C.; Spada, A.; Bosch, J.; Espinosa, E.; Molins, E. Chem. Eur. J. In press.
5. (a) Engel, R. In Handbook of Organophosphorus Chemistry; Engel, R., Ed.; Marcel Dekker: New York, 1992; Chapter 10.
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8. For some representative examples, see the following. (a) Nucleophilic phosphorus species: Scriven, E. F. V. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergamon: Oxford, 1984; Vol. 2, pp 244-247. (b) Electrophilic phosphorus species: Eymery, F.; Iorga, B.; Savignac, P. Tetrahedron 1999, 55, 13109. (c) Transition metal catalyzed methods: Hirao, T.; Masunaga, T.; Yamada, N.; Ohshiro, Y.; Agawa, T. Bull. Chem. Soc. Jpn. 1982, 55, 909. (d) Condensation processes: Monta, I.; Tada, S.; Kunimoto, K.; Tsuda, M.; Kise, M.; Kimura, K. Chem. Pharm. Bull. 1987, 35, 3898. (e) For a recent result, see: Haase, M.; Günther, W.; Görls, H.; Anders, E. Synthesis 1999, 2071. (f) Also see: Chen, D.; Martell, A. E.; Motekaitis, R. J.; McManus, D. Can. J. Chem. 1998, 76, 445.
9. For some representative examples, see the following. (a) Nucleophilic phosphorus species: Scriven, E. F. V. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergamon: Oxford, 1984; Vol. 2, pp 244-247. (b) Electrophilic phosphorus species: Eymery, F.; Iorga, B.; Savignac, P. Tetrahedron 1999, 55, 13109. (c) Transition metal catalyzed methods: Hirao, T.; Masunaga, T.; Yamada, N.; Ohshiro, Y.; Agawa, T. Bull. Chem. Soc. Jpn. 1982, 55, 909. (d) Condensation processes: Monta, I.; Tada, S.; Kunimoto, K.; Tsuda, M.; Kise, M.; Kimura, K. Chem. Pharm. Bull. 1987, 35, 3898. (e) For a recent result, see: Haase, M.; Günther, W.; Görls, H.; Anders, E. Synthesis 1999, 2071. (f) Also see: Chen, D.; Martell, A. E.; Motekaitis, R. J.; McManus, D. Can. J. Chem. 1998, 76, 445.
10. For some representative examples, see the following. (a) Nucleophilic phosphorus species: Scriven, E. F. V. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergamon: Oxford, 1984; Vol. 2, pp 244-247. (b) Electrophilic phosphorus species: Eymery, F.; Iorga, B.; Savignac, P. Tetrahedron 1999, 55, 13109. (c) Transition metal catalyzed methods: Hirao, T.; Masunaga, T.; Yamada, N.; Ohshiro, Y.; Agawa, T. Bull. Chem. Soc. Jpn. 1982, 55, 909. (d) Condensation processes: Monta, I.; Tada, S.; Kunimoto, K.; Tsuda, M.; Kise, M.; Kimura, K. Chem. Pharm. Bull. 1987, 35, 3898. (e) For a recent result, see: Haase, M.; Günther, W.; Görls, H.; Anders, E. Synthesis 1999, 2071. (f) Also see: Chen, D.; Martell, A. E.; Motekaitis, R. J.; McManus, D. Can. J. Chem. 1998, 76, 445.
11. For some representative examples, see the following. (a) Nucleophilic phosphorus species: Scriven, E. F. V. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergamon: Oxford, 1984; Vol. 2, pp 244-247. (b) Electrophilic phosphorus species: Eymery, F.; Iorga, B.; Savignac, P. Tetrahedron 1999, 55, 13109. (c) Transition metal catalyzed methods: Hirao, T.; Masunaga, T.; Yamada, N.; Ohshiro, Y.; Agawa, T. Bull. Chem. Soc. Jpn. 1982, 55, 909. (d) Condensation processes: Monta, I.; Tada, S.; Kunimoto, K.; Tsuda, M.; Kise, M.; Kimura, K. Chem. Pharm. Bull. 1987, 35, 3898. (e) For a recent result, see: Haase, M.; Günther, W.; Görls, H.; Anders, E. Synthesis 1999, 2071. (f) Also see: Chen, D.; Martell, A. E.; Motekaitis, R. J.; McManus, D. Can. J. Chem. 1998, 76, 445.
12. For some representative examples, see the following. (a) Nucleophilic phosphorus species: Scriven, E. F. V. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergamon: Oxford, 1984; Vol. 2, pp 244-247. (b) Electrophilic phosphorus species: Eymery, F.; Iorga, B.; Savignac, P. Tetrahedron 1999, 55, 13109. (c) Transition metal catalyzed methods: Hirao, T.; Masunaga, T.; Yamada, N.; Ohshiro, Y.; Agawa, T. Bull. Chem. Soc. Jpn. 1982, 55, 909. (d) Condensation processes: Monta, I.; Tada, S.; Kunimoto, K.; Tsuda, M.; Kise, M.; Kimura, K. Chem. Pharm. Bull. 1987, 35, 3898. (e) For a recent result, see: Haase, M.; Günther, W.; Görls, H.; Anders, E. Synthesis 1999, 2071. (f) Also see: Chen, D.; Martell, A. E.; Motekaitis, R. J.; McManus, D. Can. J. Chem. 1998, 76, 445.
13. For some representative examples, see the following. (a) Nucleophilic phosphorus species: Scriven, E. F. V. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergamon: Oxford, 1984; Vol. 2, pp 244-247. (b) Electrophilic phosphorus species: Eymery, F.; Iorga, B.; Savignac, P. Tetrahedron 1999, 55, 13109. (c) Transition metal catalyzed methods: Hirao, T.; Masunaga, T.; Yamada, N.; Ohshiro, Y.; Agawa, T. Bull. Chem. Soc. Jpn. 1982, 55, 909. (d) Condensation processes: Monta, I.; Tada, S.; Kunimoto, K.; Tsuda, M.; Kise, M.; Kimura, K. Chem. Pharm. Bull. 1987, 35, 3898. (e) For a recent result, see: Haase, M.; Günther, W.; Görls, H.; Anders, E. Synthesis 1999, 2071. (f) Also see: Chen, D.; Martell, A. E.; Motekaitis, R. J.; McManus, D. Can. J. Chem. 1998, 76, 445.
14. (a) Effenberger, F.; Kottmann, H. Tetrahedron 1985, 41, 4171.
15. (b) Kottmann, H.; Skarzewski, J.; Effenberger, F. Synthesis 1987, 797.
16. Choi, H. C.; Cho, K. I.; Kim, Y. H. Synlett 1995, 207.
17. All new compounds were fully characterized by physical and spectral methods (see data reported in the Supporting Information).
18. 2-EtOH) to yield diphosphonates 3. Small amounts of regioisomeric dihydropyridines 4 were isolated.
19. For related CN shifts in a similar dihydropyridine isomerization. see: Wallenfels, K.; Hanstein, W. Angew. Chem., Int. Ed. Engl. 1965, 4, 869.
20. 2, EtOAc).
21. Lavilla, R.; Gotsens, T.; Bosch, J. Synthesis 1991, 842.
22. Stout, D. M.; Meyers, A. I. Chem. Rev. 1982, 82, 223.
23. (a) Redmore, D. J. Org. Chem. 1969, 34, 1420.
24. (b) For a recent example, see: Albouy, D.; Laspéras, M.; Etemad-Moghadam, G.; Koenig, M. Tetrahedron Lett. 1999, 40, 2311.
25. (a) For an example of a phosphite acting as a leaving group, see: Horner, L.; Röder, H. Chem. Ber. 1970, 103, 2984.
26. (b) As a referee kindly suggested, an SN2′ process involving the phosphite displacement by another phosphite group would also account for the observed facts.
27. For related work, see: (a) Fowler, F. W. J. Am.. Chem. Soc. 1972, 94, 5926. (b) Bodor, N.; Pearlman, R. J. Am. Chem. Soc. 1978, 100, 4946.
28. For related work, see: (a) Fowler, F. W. J. Am.. Chem. Soc. 1972, 94, 5926. (b) Bodor, N.; Pearlman, R. J. Am. Chem. Soc. 1978, 100, 4946.
29. Calculations were performed using SPARTAN (Wavefunction Inc.) on SGI. After MM2 geometry optimization, the energy values were calculated using an AM-1 Hamiltonian (gas phase, 298 K).
30. (a) Chen, C.-K.; Hortmann, A. G.; Marzabadi, M. R. J. Am. Chem. Soc. 1988, 110, 4829.
31. (b) Yoshida, J.; Suga, S.; Suzuki, S.; Kinomura, N.; Yamamoto, A.; Fujiwara, K. J. Am. Chem. Soc. 1999, 121, 9546.
32. An intramolecular hydrogen bond between the carboxamide group and one oxygen atom of the phosphonate at position 2 was detected in the optimized structure of 3f (calculation performed with Insight II, Biosym/ MSI, on SGI).