Facile 'one-pot' preparation of phosphonothiolformates. Useful reagents for the synthesis of carbamoylphosphonates

Synlett

Volumn , Issue 6, 2000, Pages 815-816

  Salomon, Claudio J ^a,b   Breuer, Eli ^a  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

^b UNIVERSIDAD NACIONAL DE ROSARIO   (Argentina)

Author keywords

Arbuzov reaction; Carbamoylphosphonates; One pot reaction; Phosphonic acids; Phosphonothiolformates

Indexed keywords

CARBAMOYL PHOSPHATE; FORMIC ACID DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; THIOL DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; REACTION ANALYSIS; SYNTHESIS;

EID: 0034042965     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (28)

1. a) Wester, R. T.; Chambers, R. J.; Green, M. D.; Murphy, W. R.; Bioorg. Med. Chem. Lett. 1994, 4, 2005.
2. b) For review in phosphonates, see: Kafarski, P.; Lejczak, B.; Phosphorus Sulfur 1991, 63, 193.
3. Stowasser, B.; Budt, K.-H.; Jian-Qi. L.; Peyman, A.; Ruppert, D. Tetrahedron Lett. 1992, 33, 6625.
4. Liu, X.; Li, Z.; McKenna, C. E. Phosphorus Sulfur 1999, 147, 213.
5. Hirschmann, R.; Smith, A. B., III; Taylor, C. M.; Bencovic, P. A.; Taylor, S. D.; Yager, K. M.; Sprengeler, P. A.; Bencovic, S. J. Science 1994, 265, 234.
6. Helgstrand, A. J. E.; Johansson, K. N. G.; Misiorny, A.; Noren, J. O.; Stening, G. B.; European Patent Appl.; 1979; 3008, Chem. Abstr. 1980, 92, 76662.
7. Helgstrand, A. J. E.; Johansson, K. N. G.; Misiorny, A.; Noren, J. O.; Stening, G. B.; European Patent Appl.; 1979; 3008, Chem. Abstr. 1980, 92, 76662.
8. Richardson, R. G. Weed. Res. 1980, 20, 159; Wieczorek, P.; Miliszkiewicz, D.; Lejczak, B.; Soroka, M.; Kafarski, P. Pestic. Sci. 1994, 40, 57.
9. Richardson, R. G. Weed. Res. 1980, 20, 159; Wieczorek, P.; Miliszkiewicz, D.; Lejczak, B.; Soroka, M.; Kafarski, P. Pestic. Sci. 1994, 40, 57.
10. Lin, S.; Cabasso, I. J. Polym. Sci. Part A: Polym Chem. 1997, 35, 889,
11. Nagar, M. S.; Ruikar, P. B.; Mathur, J. N.; Iyer, R. H.; Synth. React. Inorg. Met.-Org. Chem. 1998, 28, 621.
12. Reetz, T.; Chadwick, D. H.; Hardy, E. E.; Kaufman, S. J. Amer. Chem. Soc. 1955, 77, 3813, and references cited therein.
13. Sekine, M.; Yamagata, H.; Hata, T. Tetrahedron Lett. 1979, 32, 3013.
14. Breuer, E.; Karaman, R.; Goldblum, A.; Leader, H.; J. Chem. Soc. Perkin Trans. 2 1988, 2029; Golomb, G.; Schlossman, A.; Saadeh, H.; Levi, M.; Van Gelder, A.; Breuer, E. Pharm. Res. 1992, 9, 143; Breuer, E.; Zaher, H.; Tashma, Z. Tetrahedron Lett. 1992, 33, 2067; Chen, R.; Breuer, E. Phosphorus Sulfur 1996, 111, 797; Breuer, E. "Acylphosphonates and their derivatives", in "The chemistry of organophosphorus compounds" Vol 4, Hartley, F. R., Ed., 1996, John Wiley & Sons, Ltd. Chichester, UK, pp 653-729.
15. Breuer, E.; Karaman, R.; Goldblum, A.; Leader, H.; J. Chem. Soc. Perkin Trans. 2 1988, 2029; Golomb, G.; Schlossman, A.; Saadeh, H.; Levi, M.; Van Gelder, A.; Breuer, E. Pharm. Res. 1992, 9, 143; Breuer, E.; Zaher, H.; Tashma, Z. Tetrahedron Lett. 1992, 33, 2067; Chen, R.; Breuer, E. Phosphorus Sulfur 1996, 111, 797; Breuer, E. "Acylphosphonates and their derivatives", in "The chemistry of organophosphorus compounds" Vol 4, Hartley, F. R., Ed., 1996, John Wiley & Sons, Ltd. Chichester, UK, pp 653-729.
16. Breuer, E.; Karaman, R.; Goldblum, A.; Leader, H.; J. Chem. Soc. Perkin Trans. 2 1988, 2029; Golomb, G.; Schlossman, A.; Saadeh, H.; Levi, M.; Van Gelder, A.; Breuer, E. Pharm. Res. 1992, 9, 143; Breuer, E.; Zaher, H.; Tashma, Z. Tetrahedron Lett. 1992, 33, 2067; Chen, R.; Breuer, E. Phosphorus Sulfur 1996, 111, 797; Breuer, E. "Acylphosphonates and their derivatives", in "The chemistry of organophosphorus compounds" Vol 4, Hartley, F. R., Ed., 1996, John Wiley & Sons, Ltd. Chichester, UK, pp 653-729.
17. Breuer, E.; Karaman, R.; Goldblum, A.; Leader, H.; J. Chem. Soc. Perkin Trans. 2 1988, 2029; Golomb, G.; Schlossman, A.; Saadeh, H.; Levi, M.; Van Gelder, A.; Breuer, E. Pharm. Res. 1992, 9, 143; Breuer, E.; Zaher, H.; Tashma, Z. Tetrahedron Lett. 1992, 33, 2067; Chen, R.; Breuer, E. Phosphorus Sulfur 1996, 111, 797; Breuer, E. "Acylphosphonates and their derivatives", in "The chemistry of organophosphorus compounds" Vol 4, Hartley, F. R., Ed., 1996, John Wiley & Sons, Ltd. Chichester, UK, pp 653-729.
18. Breuer, E.; Karaman, R.; Goldblum, A.; Leader, H.; J. Chem. Soc. Perkin Trans. 2 1988, 2029; Golomb, G.; Schlossman, A.; Saadeh, H.; Levi, M.; Van Gelder, A.; Breuer, E. Pharm. Res. 1992, 9, 143; Breuer, E.; Zaher, H.; Tashma, Z. Tetrahedron Lett. 1992, 33, 2067; Chen, R.; Breuer, E. Phosphorus Sulfur 1996, 111, 797; Breuer, E. "Acylphosphonates and their derivatives", in "The chemistry of organophosphorus compounds" Vol 4, Hartley, F. R., Ed., 1996, John Wiley & Sons, Ltd. Chichester, UK, pp 653-729.
19. Grisley, D. W. J. Org. Chem. 1961, 26, 2544.
20. Salomon, C. J. Breuer, E. Tetrahedron Lett. 1995, 36, 6759.
21. Salomon, C. J. Breuer, E. J. Org. Chem. 1997, 62, 3858.
22. 31P -5.45 ppm.
23. 31P NMR.
24. 21 132 °C); Propyl chlorothiolformate (bp 140-143 °C).
25. Gorski, R.; Dagli, D.; Patronik, V., Wemple, J. Synthesis 1974, 811.
26. Mao, M.; Franz, J.; Synthesis 1991, 920.
27. Using 2 equivalents of phosgene is important to ensure the presence of excess of phosgene during the addition of the thiol, and minimizes the formation of bisalkylthiol carbonates.
28. Aldrich Co, 1998-1999.