Статья
2020
Acid catalyzed rearrangements of aryl 3-(2-nitroaryl)oxiran-2-yl ketones
V. A. Mamedov, V. L. Mamedova, A. T. Gubaidullin, D. B. Krivolapov, G. Z. Khikmatova, E. M. Mahrous, D. E. Korshin, O. G. Sinyashin
Российский химический вестник
https://doi.org/10.1007/s11172-020-2791-x
Abstract / Full Text
Studies of chemical behavior of aryl 3-(2-nitrophenyl)oxiran-3-yl ketones in acidic medium revealed the possible occurrence of two competitive rearrangements leading to 2-(2-oxo-2-arylacetamido)benzoic acids and 3-hydroxyquinolin-4(1H)-ones.
Author information
- A. E. Arbuzov Institute of Organic and Physical Chemistry, Federal Research Center “Kazan Scientific Center of the Russian Academy of Sciences,”, 8 ul. Arbuzova, 420088, Kazan, Russian FederationV. A. Mamedov, V. L. Mamedova, A. T. Gubaidullin, D. B. Krivolapov, G. Z. Khikmatova, E. M. Mahrous, D. E. Korshin & O. G. Sinyashin
References
- R. E. Parker, N. S. Isaacs, Chem. Rev., 1959, 59, 737.
- A. S. Rao, S. K. Paknikar, J. G. Kirtane, Tetrahedron, 1983, 14, 2323.
- J. G. Smith, Synthesis, 1984, 8, 629.
- M. Sasaki, K. Takeda, Synlett, 2012, 23, 2153.
- C.-Y. Huang, A. G. Doyle, Chem. Rev., 2014, 114, 8153.
- S. Faiz, A. F. Zahoor, Mol. Diversity, 2016, 20, 969.
- V. L. Mamedova, G. Z. Khikmatova, Chem. Heterocycl. Compd., 2017, 53, 976.
- M. Fallah-Mehrjardi, A. R. Kiasat, K. Niknam, J. Iran. Chem. Soc., 2018, 15, 2033.
- J. C. Badenock, Prog. Heterocycl. Chem., 2018, 30, 43.
- S. Ahmad, A. F. Zahoor, S. A. R. Naqvi, Mol. Diversity, 2018, 22, 191.
- V. A. Mamedov, V. L. Mamedova, S. F. Kadyrova, G. Z. Khikmatova, A. T. Gubaidullin, I. Kh. Rizvanov, Sh. K. Latypov, Tetrahedron, 2015, 71, 2670.
- V. A. Mamedov, V. L. Mamedova, G. Z. Khikmatova, E. V. Mironova, D. V. Krivolapov, O. B. Bazanova, D. V. Chachov, S. A. Katsyuba, I. Kh. Rizvanov, Sh. K. Latypov, RSC Adv., 2016, 6, 27885.
- D.-H. Lan, N. Fan, Y. Wang, X. Gao, P. Zhang, L. Chen, C.-T. Au, Sh.-F. Yin, Chin. J. Catal., 2016, 37, 826.
- Y. Xia, J. Zhao, Polymer, 2018, 143, 343.
- V. A. Mamedov, V. L. Mamedova, V. V. Syakaev, D. E. Korshin, G. Z. Khikmatova, E. V. Mironova, O. B. Bazanova, I. Kh. Rizvanov, Tetrahedron, 2017, 73, 5082.
- A. T. Gubaidullin, A. I. Samigullina, Z. A. Bredikhina, A. A. Bredikhin, CrystEngComm, 2014, 16, 6716.
- A. I. Samigullina, A. T. Gubaidullin, L. V. Mustakimova, V. A. Mamedov, Russ. Chem. Bull., 2014, 63, 1444.
- V. A. Mamedov, V. L. Mamedova, G. Z. Khikmatova, E. M. Mahrous, D. E. Korshin, V. V. Syakaev, R. R. Fayzullin, E. V. Mironova, Sh. K. Latypov, O. G. Sinyashin, Russ. Chem. Bull., 2019, 68, 1020.
- J. T. Hodgkinson, W. R. J. D. Galloway, Sh. Saraf, I. R. Baxendale, S. V. Ley, M. Ladlow, M. Welch, D. R. Spring, Org. Biomol. Chem., 2011, 9, 57.
- F. Gao, K. F. Johnson, J. B. Schlenoff, J. Chem. Soc., Perkin Trans. 2, 1996, 269.
- D. A. Yushchenko, M. D. Bilokin, O. V. Pyvovarenko, G. Duportail, Y. Mely, V. G. Pivovarenko, Tetrahedron Lett., 2006, 47, 905.
- P. Hradil, J. Jirman, Coll. Czech. Chem. Commun., 1995, 60, 1357.
- P. Hradil, J. Hlavac, K. Lemr, J. Heterocycl. Chem., 1999, 36, 141.
- P. Hradil, L. Kvapil, J. Hlavac, T. Weidlich, A. Lycka, K. Lemr, J. Heterocycl. Chem., 2000, 37, 831.
- P. Hradil, M. Grepl, J. Hlavac, A. Lycka, Heterocycles, 2007, 71, 2, 269.
- M. M. Heravi, H. A. Oskooie, L. Bahrami, M. Ghassemzadeh, Ind. J. Chem., 2006, 45B, 779.
- T. W. M. Spence, G. Tennant, J. Chem. Soc. D, 1970, 1100.
- T. W. M. Spence, G. Tennant, J. Chem. Soc., 1971, 3712.
- I. P. Sword, J. Chem. Soc. (C), 1971, 820.
- APEX2 (Version 2.1), SAINTPlus. Data Reduction and Correction Program (Version 7.31A), Bruker Advanced X-ray Solutions/BrukerAXS, Inc., Madison, Wisconsin, USA, 2006.
- G. M. Sheldrick, SADABS, Program for Empirical X-Ray Absorption Correction, Bruker-Nonius, 1990-2004.
- G. M. Sheldrick, SHELXL-97, Program for Cristal Structure Refinement, University of Göttingen, Göttingen, Germany, 1997.
- L. J. Farrugia, J. Appl. Crystallorg., 1999, 32, 837.
- A. L. Spek, Acta Crystallogr., Sect. A: Found. Crystallogr., 1990, 46, part s1, 34.
- I. J. Bruno, J. C. Cole, P. R. Edgington, M. K. Kessler, C. F. Macrae, P. McCabe, J. Pearson, R. Taylor, Acta Crystallogr., Sect. B: Struct. Sci., 2002, 58, 389.