Volume 26, Issue 6 pp. 405-410

Article

Free to Read

Synthesis of Substituted N-Formylaminomethylenediphosphonates and Their Derivatives

Andrey A. Prishchenko,

Corresponding Author

Andrey A. Prishchenko

Department of Chemistry, M. V. Lomonosov Moscow State University, Moscow 119991, Russia

Correspondence to: Andrey A. Prishchenko; e-mail: [email protected].Search for more papers by this author

Mikhail V. Livantsov,

Mikhail V. Livantsov

Department of Chemistry, M. V. Lomonosov Moscow State University, Moscow 119991, Russia

Search for more papers by this author

Olga P. Novikova,

Olga P. Novikova

Department of Chemistry, M. V. Lomonosov Moscow State University, Moscow 119991, Russia

Search for more papers by this author

Ludmila I. Livantsova,

Ludmila I. Livantsova

Department of Chemistry, M. V. Lomonosov Moscow State University, Moscow 119991, Russia

Search for more papers by this author

Gleb M. Averochkin,

Gleb M. Averochkin

Department of Chemistry, M. V. Lomonosov Moscow State University, Moscow 119991, Russia

Search for more papers by this author

Valery S. Petrosyan,

Valery S. Petrosyan

Department of Chemistry, M. V. Lomonosov Moscow State University, Moscow 119991, Russia

Search for more papers by this author

Andrey A. Prishchenko,

Corresponding Author

Andrey A. Prishchenko

Department of Chemistry, M. V. Lomonosov Moscow State University, Moscow 119991, Russia

Correspondence to: Andrey A. Prishchenko; e-mail: [email protected].Search for more papers by this author

Mikhail V. Livantsov,

Mikhail V. Livantsov

Department of Chemistry, M. V. Lomonosov Moscow State University, Moscow 119991, Russia

Search for more papers by this author

Olga P. Novikova,

Olga P. Novikova

Department of Chemistry, M. V. Lomonosov Moscow State University, Moscow 119991, Russia

Search for more papers by this author

Ludmila I. Livantsova,

Ludmila I. Livantsova

Department of Chemistry, M. V. Lomonosov Moscow State University, Moscow 119991, Russia

Search for more papers by this author

Gleb M. Averochkin,

Gleb M. Averochkin

Department of Chemistry, M. V. Lomonosov Moscow State University, Moscow 119991, Russia

Search for more papers by this author

Valery S. Petrosyan,

Valery S. Petrosyan

Department of Chemistry, M. V. Lomonosov Moscow State University, Moscow 119991, Russia

Search for more papers by this author

First published: 16 June 2015

https://doi.org/10.1002/hc.21274

Citations: 14

Contract grant sponsor: Russian Foundation for Basic Research.

Contract grant numbers: 14-03-00001 and 15-03-00002.

Share a link

Email
Wechat
Bluesky

ABSTRACT

The convenient methods for the synthesis of new trimethylsilyl esters of aminomethylenediphosphonic acids are elaborated. The new substituted N-formylaminomethylenediphosphonates are obtained via the interaction of trimethylsilyl esters of methylenediphosphonic acids with a mixture of triethyl orthoformate and ethanol. Also boron trifluoride–diethyl etherate as an effective catalyst is used for the interaction of hydrochlorides of ethoxymethylene imines with diethyl trimethylsilyl phosphite. The corresponding aminomethylenediphosphonic acids are presented.

REFERENCES

1(a) Kukhar, V. P.; Hudson, H. R. In Chemistry and Biological Activity: Wiley: New York, 2000
Google Scholar
(b) Ebetino, F. H. Phosphorus Sulfur Silicon Relat Elem 1999, 144–146, 9–12;
Web of Science® Google Scholar
(c) Fields, S. C. Tetrahedron 1999, 55, 12237–12273;
10.1016/S0040-4020(99)00701-2
CAS Web of Science® Google Scholar
(d) Grigoriev, E. V.; Yashina, N. S.; Prishchenko, A. A.; Livantsov, M. V.; Petrosyan, V. S; Pellerito, L.; Schafer, M. J. Appl Organometal Chem 1993, 7, 353–355;
10.1002/aoc.590070509
Web of Science® Google Scholar
(e) Grigoriev, E. V.; Yashina, N. S.; Prischenko, А. А.; Livantsov, M. V.; Petrosyan, V. S.; Massa, W.; Harms, K.; Wocadlo, S.; Pellerito, L. Appl Organometal Chem 1995, 9, 11–22.
10.1002/aoc.590090104
CAS Web of Science® Google Scholar
2(a) Krasovskaya, S. M.; Uzhinova, L. D.; Andrianova, M. Y.; Prishchenko, A. A.; Livantsov, M. V. Biomaterials 1991, 12, 817–820;
10.1016/0142-9612(91)90067-K
CAS PubMed Web of Science® Google Scholar
(b) Takeuchi, M.; Sakamoto, S.; Yoshida, M.; Abe, T.; Isomura, Y. Chem Pharm Bull 1993, 41, 688–693;
10.1248/cpb.41.688
CAS PubMed Web of Science® Google Scholar
(c) Ghosh, S.; Chan, J. M. V.; Andrianova, M. Y.; Lea, C. R.; Meints, G. A.; Lewis, J. C.; Tovian, Z. S.; Flessner, R. M.; Loftus, T. C.; Bruchhaus, I.; Kendrick, H.; Croft, S. L.; Kemp, R. G.; Kobayashi, S.; Nozaki, T.; Oldfield, E. J Med Chem 2004, 47, 175–187.
10.1021/jm030084x
CAS PubMed Web of Science® Google Scholar
3(a) Tyurin, V. Yu.; Gracheva, Yu. A.; Milaeva, E. R.; Prishchenko, A. A.; Livantsov, M. V.; Novikova, O. P.; Livantsova, L. I.; Maryashkin, A. V.; Bubnov, M. P.; Kozhanov, K. A.; Cherkasov, V. K. Russ Chem Bull 2007, 56, 4, 774–780;
10.1007/s11172-007-0116-y
CAS Web of Science® Google Scholar
(b) Prishchenko, A. A.; Livantsov, M. V.; Novikova, O. P.; Livantsova, L. I.; and Milaeva, E. R. Heteroatom Chem 2008, 19, 490–494;
10.1002/hc.20458
CAS Web of Science® Google Scholar
(c) Prishchenko, A. A.; Livantsov, M. V.; Novikova, O. P.; Livantsova, L. I.; Petrosyan, V. S. Heteroatom Chem 2012, 23, 32–40;
10.1002/hc.20749
CAS Web of Science® Google Scholar
(d) Berberova, N. T.; Osipova, V. P.; Kolyada, M. N.; Antonova, N. A.; Zefirov, N. S.; Milaeva, E. R.; Filimonova, S. I.; Gracheva, Yu. A.; Prishchenko, A. A.; Livantsov, M. V.; Livantsova L. I.; Novikova, O. P. Patent RU 2405032 C 1, Rus Patent Bull 2010, 33 (in Russian);
Google Scholar
(e) Berberova, N. T.; Chernushkina, I. M.; Osipova, V. P.; Kolyada, M. N.; Pimenov, Yu. I.; Gracheva, Yu. A.; Prishchenko, A. A.; Livantsov, M. V.; Livantsova, L. I.; Novikova, O. P.; Milaeva, E. R.; Zefirov, N. S. Patent RU 2457240 C 2, Rus Patent Bull 2012, 21 (in Russian).
Google Scholar
4(a) Prishchenko, A. A.; Livantsov, M. V.; Novikova, O. P.; Livantsova, L. I.; Petrosyan, V. S. Heteroatom Chem 2009, 20, 319–324;
10.1002/hc.20552
CAS Web of Science® Google Scholar
(b) Prishchenko, A. A.; Livantsov, M. V.; Novikova, O. P.; Livantsova, L. I.; Ershov, I. S.; Petrosyan, V. S. Heteroatom Chem 2013, 24, 355–360;
10.1002/hc.21100
CAS Web of Science® Google Scholar
(c) Prishchenko, A. A.; Livantsov, M. V.; Novikova, O. P.; Livantsova, L. I.; Ershov, I. S.; Petrosyan, V. S. Heteroatom Chem 2015, 26, 101–105.
10.1002/hc.21220
CAS Web of Science® Google Scholar
5Prishchenko, A. A.; Livantsov, M. V.; Novikova, O. P.; Livantsova, L. I.; Petrosyan, V. S. Heteroatom Chem 2010, 21, 236–241.
10.1002/hc.20602
CAS Web of Science® Google Scholar
6(a) Ploeger, W.; Schindler, N.; Wollmann, K.; Worms, K. H. Z Anorg allg Chem 1972, 389, 119–128 (in German);
10.1002/zaac.19723890203
CAS Web of Science® Google Scholar
(b) Li, J. J. Name Reactions; Springer-Verlag: Berlin, 2003;
10.1007/978-3-662-05336-2
Google Scholar
(c) Gross, H.; Costisella, B., Gnauk, T., Brennecke, L. J Prakt Chem 1976, 318, 116–126 (in German).
10.1002/prac.19763180113
CAS Web of Science® Google Scholar
7(a) Kafarski, P.; Lejczak, B. Synthesis 1988, 307–310;
10.1055/s-1988-27550
CAS Web of Science® Google Scholar
(b) Zymanczyk-Duda, E.; Lejczak, B.; Kafarski, P. Phosphorus Sulfur Silicon Relat Elem 1996, 112, 47–56;
10.1080/10426509608046348
CAS Web of Science® Google Scholar
(c) Maier, L. Phosphorus Sulfur 1981, 11, 311–322.
10.1080/03086648108077429
CAS Web of Science® Google Scholar
8(a) Orlovskii, V. V.; Vovsi, B. A. Russ J Gen Chem 1976, 46, 294-300 (in Russian);
Google Scholar
(b) Midrier, C.; Lantsoght, M.; Volle, J.-N.; Pirat, J.-L.; Virieux, D.; Stevens, C. V. Tetrahedron Lett 2011, 52, 6693–6696.
10.1016/j.tetlet.2011.09.096
CAS Web of Science® Google Scholar
9(a) Wozniak, L.; Chojnowski, J. Tetrahedron 1989, 45, 2465–2524;
10.1016/S0040-4020(01)80083-1
CAS Web of Science® Google Scholar
(b) Romanenko, V. D.; Shevchuk, M. V.; Kukhar, V. P. Curr Org Chem 2011, 15, 2774–2801.
10.2174/138527211796378505
CAS Web of Science® Google Scholar

Citing Literature

All articles

Synthesis of Substituted N-Formylaminomethylenediphosphonates and Their Derivatives

ABSTRACT

REFERENCES

Citing Literature

References

Information

About Wiley Online Library

Help & Support

Opportunities

Connect with Wiley

Synthesis of Substituted N-Formylaminomethylenediphosphonates and Their Derivatives

ABSTRACT

REFERENCES

Citing Literature

References

Related

Information