1-Azidoalkylphosphosphonates - A Convenient Substrates for the Synthesis of N-Alkyl alfa-Aminoalkylphosphonates

Gajda, T.; Janik, D.

Artykuł - szczegóły

Tytuł artykułu

1-Azidoalkylphosphosphonates - A Convenient Substrates for the Synthesis of N-Alkyl alfa-Aminoalkylphosphonates

Autorzy

Gajda T. , Janik D.

Identyfikatory

Warianty tytułu

Języki publikacji

Abstrakty

Diethyl [1-(alkylamino)alkyl]phosphonates 5 have been efficiently synthesized via a two-step reaction of diethyl 1-azidoalkylphosphonates 1 with triphenylphosphine, followed by in situ transformation of thus formed phosphazenes2 into imines 4 by means of aldehydes and subsequent reduction of 4 with sodium borohydride in ethanol.

Słowa kluczowe

phosphazenes Staudinger reaction diethyl 1-azidoalkylphosphonates reduction aminophosphonates

Wydawca

Polskie Towarzystwo Chemiczne

Czasopismo

Polish Journal of Chemistry

Rocznik

2005

Tom

Vol. 79 / nr 3

Strony

493--498

Opis fizyczny

Bibliogr. poz. 18, rys.

Twórcy

autor

Gajda T.

Institute of Organic Chemistry, Technical University of ?ód?, Żeromskiego St. 116, 90-924 Łódź, Poland

autor

Janik D.

Institute of Organic Chemistry, Technical University of ?ód?, Żeromskiego St. 116, 90-924 Łódź, Poland

Bibliografia

1. Aminophosphonic and Aminophosphinic Acids. Chemistry and Biological Activity, Eds V. P. Kukhar and H. R. Hudson, John Wiley and Sons, Chichester, 2000.
2. Kafarski P. and Lejczak B., Phosphorus Sulﬁar Silicon, 63, 193 (1991). '
3. Fields E.K.,J. Am. Chem. Soc., 74, 1528 (1952); Pudovik A.N.,DokI. Akad. NaukSSSR, 83, 865 (1953); Tyka R., Tetrahedron Lett., 677 (1 970); Afarinkia K., Rees C.W. and Cadogan H., Tetrahedron, 46, 7175 (1990).
4. Oleksyszyn J., Synthesis, 722 (1980).
5. Edmundson R.S., The Chemistry of Organophosphorus Compounds, Ed. F.R. Hartley, Wiley, Chichester 1996, Vol. 4, Ch. 4, p. 293.
6. Preliminary communication: Gajda T., Sikora D. and Nonas T., Phosphorus SuIﬁur Silicon, 144-146, 581 (1999). Proceedings of the XIVth Intemational Conference on Phosphorus Chemistry.
7. Mortier J., Gridnev I.D. and Fortineau A-D., Org. Lett., 1, 981 (1999).
8. Scriven E.F.V. and Tumbull K., Chem. Rev., 88, 351 (1988); Hughes D.L., Organic Reactions, vol. 42, 335 (1992) Wiley New York.
9. Gajda T., Koziara A., Osowska-Pacewicka K., Zawadzki S. and Zwierzak A., Synth. Commun., 22, 1929(1992).
10. Gajda T. and Mamsiak M., Synthesis, 367 (1992). 87
11. Cadogan J.I.G. and Mackie R.K., Chem. Sac. Rev , 3, 87, (1974); Eguchi S., Matsuschita Z., Zamashita K., Org. Prep. Proced. Int., 24, 209 (1992).
12. Katritzky A.R., Jiang J. and GreenhillI.V., J Org. Chem., 58, 1987 (1993); Katritzky A.R., Zhang G. and Jiang J., J. Org. Chem., 59, 4556 (1994); Palacios F., Ochoa de Retana A.M. and Pagalday J., Eur. J. Org. Chem., 913 (2003); Palacios F., Ochoa de Retana A.M., Martinez de Margiorta E., Rodriguez M. and Pagalday J., Tetrahedron, 59, 2617 (2003); Palacios F., Alonso C., Pagalday J., Ochoa de Retana A.M. and Rubiales G., Org. Biomol. Chem., 1, 1112 (2003).
13. Gajda T. and Matusiak M., Synth. Commun., 22, 2193 (1992).
14. Gajda T., Tetrahedron: Asymmetry, 5, 1965 (1994).
15. Sikora D. and Gajda T., Phosphorus Sulfur and Silicon, 157, 201 (2000).
16. Staudinger H. and Hauser E., Helu Chim. Acta, 4, 861 (1921); Gololobov Y.G. and Kasukhin L.F., Tetrahedran, 48, 1353 (1992) and references clted therem.
17. Ratcliffe R.W. and Christensen B.G., Tetrahedron Lett., 4645 (1973); Lewis R.T., and Motherwell W.B.,Tetrahedran, 48, 1465 (1992); Afarinkia K., Rees C.W. and Cadogan J.I.G., Tetrahedron, 46, 7175 (1990) ; Lukanov L.K. and Venkov A.P., Synthesis, 263 (1992), Oberhauser T. and Meduna V., Tetrahedron, 52, 7691 (1996).
18. Couture A., Deniau E., Woisel P. and Grandclaudon P., Tetrahedron Lett., 36, 2483 (1995).

Typ dokumentu

Bibliografia

Identyfikator YADDA

bwmeta1.element.baztech-article-BUJ3-0002-0057