Efficient and convenient one-pot synthesis of phosphoramidates and phosphates

Synthetic Communications

Volumn 37, Issue 19, 2007, Pages 3403-3407

  Gupta, A K ^a   Acharya, J ^a   Dubey, D K ^a   Kaushik, M P ^a  

^a DEFENCE RESEARCH AND DEVELOPMENT ESTABLISHMENT   (India)

Author keywords

Dialkylphosphites; Phosphates; Phosphoramidates; Trichloroisocyanuric acid

Indexed keywords

ACETONITRILE; ALCOHOL DERIVATIVE; CYANURIC ACID; DIAMINE; PHOSPHATE; PHOSPHITE; PHOSPHORAMIDIC ACID DERIVATIVE; SYMCLOSENE; TRIAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ONE POT SYNTHESIS; REACTION TIME;

EID: 35148835310     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910701483662     Document Type: Article

References (14)

1. (a) Eto, M. Organophosphorus Pesticides. In Organic and Biological Chemistry; CRC Press: Boca Raton, FL, USA, 1974;
2. (b) Van Wazer, J. R. Phosphorus and its Compounds, Vol. II. Wiley; Interscience: New York, 1961;
3. (c) Engel, R. Phosphonates as analogues of natural phosphates. Chem. Rev. 1977, 77, 349.
4. Kosolapoff, G. M. In Organic Phosphorus Compounds. Vol. 6. Wiley-Interscience: New York, 1950, p. 503.
5. Gryaznov, S.; Skorski, T.; Cucco, C.; Nieborowska-Skorska, M.; Chiu, C. Y.; Lloyd, D.; Chen, J. K.; Koziolkiewiez, M.; Calabretta, B. Oligonucleotide N3′-P5′ phosphoramidates as anti-sense agents. Nucleic Acids Res. 1996, 24, 1508.
6. Uhlmann, E.; Peyman, A. Antisense oligonucleotide: A new therapeutic principle. Chem. Rev. 1990, 90, 543.
7. (a) Afarinkia, K.; Vinader, M. V. In Comprehensive Organic Functional Group Transformations. Vol. 5, Moody, C. J., Ed.; Pergamon: London, 1995, 393;
8. (b) Savignac, P.; Iorga, B. Modern Phosphorus Chemistry; CRC Press: New York, 2003, p. 319;
9. (c) Denmark, S. E.; Stavenger, R. A. Asymmetric catalysis of aldol reactions with chiral lewis bases. Acc. Chem. Res. 2000, 33, 432.
10. (a) Westheimer, F. H. Why nature chose phosphates. Science 1987, 235, 1173;
11. (b) Di Novi, M.; Trainor, D. A;. Nakanishi, K. The structure of PB-1, an unusual toxin isolated from the red tide dinoflagellate Ptychodiscus brevis. Tetrahedron Lett. 1983, 24, 855.
12. Corbridge, D. E. C. Phosphorus: An Outline of its Chemistry, Biochemistry and Technology, 4th edn.; Elsevier Science: Amsterdam, The Netherlands, 1990, Chapter 5, p. 403.
13. Gupta, A. K.; Shakya, P. D.; Pardasani, D.; Dubey, D. K. Mass spectral analysis of synthones of nerve agents for verification of the chemical weapons convention. Rapid Commun. Mass Spectrom. 2005, 19, 975.
14. Gupta, A. K. Synthetic studies on organophosphorus compounds. PhD thesis. Jiwaji University, Gwalior, India, 2003.