Synthesis of Diphenyl α-(Dipropoxyphosphoramido)alkylphosphonates
Zhan-Wei CUI
State Key Laboratory of Elemento-organic Chemistry, Research Institute of Elemento-organic Chemistry, Nankai University, Tianjin 300071, China
Search for more papers by this authorJian-Feng ZHANG
State Key Laboratory of Elemento-organic Chemistry, Research Institute of Elemento-organic Chemistry, Nankai University, Tianjin 300071, China
Search for more papers by this authorRu-Yu CHEN
Search for more papers by this authorZhan-Wei CUI
State Key Laboratory of Elemento-organic Chemistry, Research Institute of Elemento-organic Chemistry, Nankai University, Tianjin 300071, China
Search for more papers by this authorJian-Feng ZHANG
State Key Laboratory of Elemento-organic Chemistry, Research Institute of Elemento-organic Chemistry, Nankai University, Tianjin 300071, China
Search for more papers by this authorRu-Yu CHEN
Search for more papers by this authorAbstract
A convenient method has been developed for the synthesis of diphenyl α-(dipropoxyphosphoramido)alkyl- phosphonates under mild conditions, namely the reaction of dipropyl phosphoramidate (1) with a para- (un)substituted benzaldehyde or cyclicketone (2) and triphenyl phosphite (3) by a one-pot procedure with the aid of acetyl chloride.
REFERENCES
- 1 Emsley, J.; Hall, E. D., The Chemistry of Phosphorus, Harper and Row, London, 1976.
- 2 Kafarski, P.; Lejczak, B.. Phosphorus, Sulfur, Silicon Relat Elem., 1991, 63, 193.
- 3a Hirschmann, R.; Smith, A. B. III.; Taylor, C.; Benkovic, P.; Taylor, S.; Yager, K.; Sprengler, P.; Benkovic, S.. Science, 1994, 265, 234.
- 3b Smith, A. B. III.; Taylor, C. M.; Benkovic, J.; Hirtchmann, R.. Tetrahedron Lett., 1994, 35, 6853.
- 4a Allen, M.; Fuhrer, W.; Tuck, B.; Wade, R.; Wood, J.. J. Med. Chem., 1989, 32, 1652.
- 4b Burke, T. R.; Barchi, J. J.; George, C.; Wolf, G.; Shoelson, S. E.; Yan, X.. J. Med. Chem., 1995, 38, 1386.
- 5 Atherton, F.; Hassall, C.; Lambert, R.. J. Med. Chem., 1986, 29, 29.
- 6a Allen, J.; Hassall, C.; Atherton, F.; Hall, M.; HassalL, C.; Holmes, S.; Lambert, R.; Nisbet, L.; Ringrose, P.. Nature, 1978, 272, 56.
- 6b Allen, J.; Atherton, F.; Hall, M.; Hassall, C.; Lambert, R.; Nisbet, L.; Ringrose, P.. Antimicro. Agents Chemother., 1979, 15, 684.
- 6c Atherton, F.; Hall, M.; Hassall, C.; Lambert, R.; Ringrose, P.. Antimicro. Agents Chemother., 1979, 15, 677.
- 6d Atherton, F.; Hall, M.; Hassall, C.; Lambert, R.; Lloyd, W.; Ringrose, P.. Antimicro. Agents Chemother., 1979, 15, 696.
- 7a Shuman, C. F.; Vrang, L.; Danielson, U. H.. J. Med. Chem., 2004, 47, 5953.
- 7b Meier, G.; Krause, M.; Huls, A.; Ligneau, X.; Pertz, H. H.; Arrang, J. M.; Ganellin, C. R.; Schwartz, J. C.; Schu- nack, W.; Stark, H.. J. Med. Chem., 2004, 47, 2678.
- 8a Cruz, A. De. la.; Koeller, K. J.; Rath, N. P.; Spilling, C. D.; Vasconcelos, I. C. F.. Tetrahedron, 1998, 54, 10513.
- 8b Zhou, J.; Chen, R. Y.; Yang, X. F.. Heteroatom Chem., 1998, 9, 369.
- 8c Zhou, J.; Chen, R. Y.. J. Chem. Soc., Perkin Trans. 1, 1998, 2917.
- 8d Kabachnik, M. M.; Zobnina, E. V.; Beletskaya, I. P.. Synlett, 2005, 1393.
- 9 Oleksyszyn, J.; Powers, J. C.. Biochemistry, 1991, 30, 485.
- 10 Stroud, R. M.; Kay, L. M.; Dickerson, R. E.. J. Mol. Biol., 1974, 83, 185.
- 11a Oleksyszyn, J.; Tyka, R.. Tetrahedron Lett., 1977, 2823.
- 11b Huber, III J. W.; Middlebrooks, M.. Synthesis, 1977, 883.
- 11c Huber, III J. W.; Gilmore, W. F.. Tetrahedron Lett., 1979, 3049.
- 11d Oleksyszyn, J.; Subotkowska, L.. Synthesis, 1980, 906.
- 11e Tam, C. C.; Mattocks, K.; Tishler, M.. Synthesis, 1982, 188.
- 12 Yuan, C. Y.; Chen, S. J.; Wang, G. H.. Synthesis, 1991, 490.
- 13a Oleksyszyn, J.; Gruszecha, E.. Tetrahedron Lett., 1981, 3537.
- 13b Yuan, C. Y.; Yuan, Q.; Xie, X. K.. Chin. J. Org. Chem., 1989, 9, 136 (in Chinese).
- 13c Oleksyszyn, J.. Synthesis, 1981, 444.
- 14a Yuan, C. Y.; Qi, Y. M.. Synthesis, 1986, 821.
- 14b Yuan, C. Y.; Qi, Y. M.. Synthesis, 1988, 472.
- 14c Yuan, C. Y.; Wang, G. H.; Chen, S. J.. Synthesis, 1990, 522.
- 15a
Cherkasov, R. A.;
Galkin, V. I..
Russ. Chem. Rev.,
1998,
67,
857.
10.1070/RC1998v067n10ABEH000421 Google Scholar
- 15b Miao, Z. W.; Wang, B.; Zhang, G. H.; Chen, R. Y.. Bioorg. Chem., 2006, 34, 167.
- 16 Li, Z. G.; Wang, Q. M.; Huang, J. M., Synthesis of Organic Intermediates, Chemistry Engineering Industry Press, Beijing, 2001, p. 205 (in Chinese).
