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Ultrasound-assisted Synthesis of Azlactone and its Reactions with Nucleophiles

Boris Vladimirovich Paponov 1
Boris Vladimirovich Paponov
, 
Sergey Vital'evich Lvov 2
Sergey Vital'evich Lvov
, 
Ekaterina Vasil'evna Ichetovkina 1
Ekaterina Vasil'evna Ichetovkina
, 
Ilya Alexandrovich Panasenko 1
Ilya Alexandrovich Panasenko
, 
Stepan G Stepanian 3
Stepan G Stepanian
1 Department of Chemistry, V.N. Karazin Khar'kov National University, Khar'kov, Ukraine
2 Research Institute of Biology, V.N. Karazin Khar'kov National University, Khar'kov, Ukraine
3 B.I. Verkin Physicotechnical Institute for Low Temperatures, National Academy of Sciences of Ukraine, Kharkov, Ukraine
10.1016/j.mencom.2012.09.016
Published 2012-09-17
Communication , Volume 22, Issue 5, 273-274
6
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Paponov B. V. et al. Ultrasound-assisted Synthesis of Azlactone and its Reactions with Nucleophiles // Mendeleev Communications. 2012. Vol. 22. No. 5. pp. 273-274.
GOST all authors (up to 50) Copy
Paponov B. V., Lvov S. V., Ichetovkina E. V., Panasenko I. A., Stepanian S. G. Ultrasound-assisted Synthesis of Azlactone and its Reactions with Nucleophiles // Mendeleev Communications. 2012. Vol. 22. No. 5. pp. 273-274.
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TY - JOUR
DO - 10.1016/j.mencom.2012.09.016
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2012.09.016
TI - Ultrasound-assisted Synthesis of Azlactone and its Reactions with Nucleophiles
T2 - Mendeleev Communications
AU - Paponov, Boris Vladimirovich
AU - Lvov, Sergey Vital'evich
AU - Ichetovkina, Ekaterina Vasil'evna
AU - Panasenko, Ilya Alexandrovich
AU - Stepanian, Stepan G
PY - 2012
DA - 2012/09/17
PB - Mendeleev Communications
SP - 273-274
IS - 5
VL - 22
ER -
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@article{2012_Paponov,
author = {Boris Vladimirovich Paponov and Sergey Vital'evich Lvov and Ekaterina Vasil'evna Ichetovkina and Ilya Alexandrovich Panasenko and Stepan G Stepanian},
title = {Ultrasound-assisted Synthesis of Azlactone and its Reactions with Nucleophiles},
journal = {Mendeleev Communications},
year = {2012},
volume = {22},
publisher = {Mendeleev Communications},
month = {Sep},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2012.09.016},
number = {5},
pages = {273--274},
doi = {10.1016/j.mencom.2012.09.016}
}
MLA
Cite this
MLA Copy
Paponov, Boris Vladimirovich, et al. “Ultrasound-assisted Synthesis of Azlactone and its Reactions with Nucleophiles.” Mendeleev Communications, vol. 22, no. 5, Sep. 2012, pp. 273-274. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2012.09.016.

Keywords

azlactone
Erlenmeyer-Plöchl reaction
oxindole
ultrasound

Abstract

4-(2-Oxoindolin-3-ylidene)-2-phenyl-5(4H)-oxazolone (azlactone) was synthesized as a mixture of E- and Z-isomers by ultrasound-assisted Erlenmeyer–Plöchl reaction between isatin and N-benzoylglycine. Treatment of azlactone with nucleophiles causes opening of its oxazolone moiety.

References

2.
Antiangiogenic versus cytotoxic activity in analogues of aeroplysinin-1
Córdoba R., Tormo N.S., Medarde A.F., Plumet J.
Bioorganic and Medicinal Chemistry, 2007
5.
10.1016/j.mencom.2012.09.016_bib0010
Erlenmeyer
Liebigs Ann. Chem., 1893
6.
H. E. Carter, in Organic Reactions, ed. R. Adams, John Wiley, New York, 1947, vol. 3, p. 198.
8.
MIXED BENZOINS. VIII. FURTHER DETERMINATIONS OF STRUCTURES. QUESTION OF ISOMERS
Buck J.S., Ide W.S.
Journal of the American Chemical Society, 1932
11.
Study on dry-media microwave azalactone synthesis on different supported KF catalysts: influence of textural and acid–base properties of supports
Bautista F.M., Campelo J.M., García A., Luna D., Marinas J.M., Romero A.A.
Journal of the Chemical Society Perkin Transactions 2, 2002
12.
10.1016/j.mencom.2012.09.016_bib0025
Vine
Chem., 2009
13.
Antitumor Activity of New Substituted 3-(5-Imidazo[2,1-b]thiazolylmethylene)-2-indolinones and Study of Their Effect on the Cell Cycle
Andreani A., Granaiola M., Leoni A., Locatelli A., Morigi R., Rambaldi M., Garaliene V., Welsh W., Arora S., Farruggia G., Masotti L.
Journal of Medicinal Chemistry, 2005
14.
Antitumor Activity of New Substituted 3-(5-Imidazo[2,1-b]thiazolylmethylene)-2-indolinones and 3-(5-Imidazo[2,1-b]thiadiazolylmethylene)-2-indolinones: Selectivity against Colon Tumor Cells and Effect on Cell Cycle-Related Events
Andreani A., Burnelli S., Granaiola M., Leoni A., Locatelli A., Morigi R., Rambaldi M., Varoli L., Calonghi N., Cappadone C., Voltattorni M., Zini M., Stefanelli C., Masotti L., Shoemaker R.H., et. al.
Journal of Medicinal Chemistry, 2008
15.
Design, synthesis and biological evaluation of novel 4-thiazolidinones containing indolin-2-one moiety as potential antitumor agent
Wang S., Zhao Y., Zhang G., Lv Y., Zhang N., Gong P.
European Journal of Medicinal Chemistry, 2011
16.
A. H. Abdel-Rahman, E.M. Keshk, M.A. Hanna and Sh M. El-Bady, Bioorg. Med. Chem., 2004, 12, 2483.
17.
10.1016/j.mencom.2012.09.016_bib0040_2
Kandile
Rev. Roum. Chim., 1991
18.
V. A. Chebanov, S.M. Desenko, S.A. Kuzmenko, V.A. Borovskoy, V.I. Musatov and Yu. V. Sadchikova, Izv. Akad. Nauk, Ser. Khim., 2004, 2730.(Russ. Chem. Bull., Int. Ed., 2004, 53, 2845).
19.
S. V. Kolisnyk, V.V. Bolotov, O.O. Altukhov and S. V. Shishkina, Zh. Org. Paratsevtych. Khim., 2011, (2), 53.(in Ukrainian).
20.
V. V. Bolotov, S.N. Kovalenko, S.V. Kovaleva and V. I. Stepanenko, Khim. Geterotsikl. Soedin., 2004, 249.[Chem. Heterocycl. Compd. (Engl. Transl.), 2004, 40, 211].
21.
10.1016/j.mencom.2012.09.016_bib0060
Subhashini
Indian J. Chem., Sect. B, 1987