Abstract
The review integrates and systematizes the key chemical transformations of monothiooxamides and thiohydrazides of oxamic acids and their derivatives, which give rise to various five-, six-, and seven-membered heterocyclic compounds with several heteroatoms.
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Pat. WO 2010/036147; https://worldwide.espacenet.com.
I. V. Zavarzin, V. V. Chertkova, I. S. Levina, E. I. Chernoburova, Russ. Chem. Rev., 2011, 80, 661.
X. Dongsheng, W. Yanchao, X. Jin, L. Jun, C. Junjun, Z. Man, F. Lei, W. Yongxiang, Med. Chem. Res., 2014, 23, 4977.
M. Chao, W. Anhui, W. Yongqi, R. Xuhong, C. Maosheng, Arch. Pharm., 2013, 346, 891.
Pat. WO 2013/074059; https://worldwide.espacenet.com.
Pat. WO 2013/018804; https://worldwide.espacenet.com.
Pat. WO 2012/095521; https://worldwide.espacenet.com.
Pat. WO 2011/080176; https://worldwide.espacenet.com.
M. A. Abdallah, T. A. Farghaly, M. M. Abdalla, Z. A. Muhammad, World J. Chem., 2011, 6, 96.
T. A. Farghaly, I. M. Abass, M. M. Abdalla, R. O. A. Mahgoub, World J. Chem., 2011, 6, 8.
D. V. Shamshurin, I. V. Zavarzin, V. N. Yarovenko, A. A. Es’kov, E. I. Chernoburova, M. M. Krayushkin, Y. V. Volgin, E. N. Shapovalova, P. N. Nesterenko, O. A. Shpigun, Mendeleev Commun., 2005, 15, 143.
M. M. Krayushkin, V. N. Yarovenko, I. V. Zavarzin, Russ. Chem. Bull. (Int. Ed.), 2004, 53, 517.
N. A. Zigangirova, E. S. Zayakin, L. N. Kapotina, E. A. Kost, L. V. Didenko, D. Yu. Davydova, Yu. P. Rumyantseva, A. L. Gintsburg, Acta Naturae, 2012, 2, 90.
RF Pat. 2495036; Byul. izobret., 2013, No. 28.
RF Pat. 2447066; Byul. izobret., 2012, No. 10.
V. N. Yarovenko, I. V. Zavarzin, M. M. Krayushkin, S. A. Kosarev, Russ. Chem. Bull. (Int. Ed.), 2002, 51, 1504.
Y. A. Volkova, E. I. Chernoburova, A. S. Petrova, A. A. Shtil, I. V. Zavarzin, Phosphorus, Sulfur, Silicon, 2017, 192, 237.
V. N. Yarovenko, A. V. Polushina, I. V. Zavarzin, M. M. Krayushkin, S. K. Kotovskaya, V. N. Charushin, J. Sulfur Chem., 2009, 30, 327.
V. N. Yarovenko, A. V. Polushina, K. S. Levchenko, I. V. Zavarzin, M. M. Krayushkin, S. K. Kotovskaya, V. N. Charushin, Russ. Chem. Bull. (Int. Ed.), 2009, 58, 1276.
V. N. Yarovenko, A. V. Polushina, K. S. Levchenko, I. V. Zavarzin, M. M. Krayushkin, S. K. Kotovskaya, V. N. Charushin, Russ. J. Org. Chem., 2007, 43, 1387.
N. Zh. Rakhimzhanova, Ph.D Thesis (Chemistry), Institute of Organic Synthesis and Coal Chemistry of the Kazakhstan, Karaganda, 2008 (in Russian).
M. Krasavin, A. Lukin, N. Zhurilo, A. Kovalenko, I. Zahanich, S. Zozulya, D. Moore, I. G. Tikhonova, Bioorg. Med. Chem., 2016, 24, 2954.
M. Krasavin, A. Lukin, N. Zhurilo, A. Kovalenko, I. Zahanich, S. Zozulya, J. Enzyme Inhib. Med. Chem., 2016, 31, 1404.
M. Krasavin, A. Lukin, A. Bakholdina, N. Zhurilo, O. Onopchenko, P. Borysko, S. Zozulya, D. Moore, I. G. Tikhonova, Eur. J. Med. Chem., 2017, 140, 229.
V. N. Yarovenko, A. V. Shirokov, I. V. Zavarzin, O. N. Krupinova, A. V. Ignatenko, M. M. Krayushkin, Chem. Heterocycl. Compd., 2003, 39, 1633.
K. A. Myannik, V. N. Yarovenko, E. K. Beloglazkina, A. A. Moiseeva, M. M. Krayushkin, Polyhedron, 2018, 139, 208.
K. A. Myannik, E. K. Beloglazkina, A. A. Moiseeva, T. K. Baryshnikova, V. N. Yarovenko, M. M. Krayushkin, Mendeleev Commun., 2018, 28, 79.
E. S. Zayakin, Ph.D Thesis (Chemistry), N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, 2009 (in Russian).
K. A. Myannik, V. N. Yarovenko, G. M. Rodionova, T. K. Baryshnikova, M. M. Krayushkin, ARKIVOC, 2017, iii, 316.
I. V. Zavarzin, Ya. S. Antonov, E. I. Chernoburova, M. A. Shchetinina, N. G. Kolotyrkina, A. S. Shashkov, Russ. Chem. Bull. (Int. Ed.), 2013, 62, 2603.
I. V. Zavarzin, Ya. S. Antonov, E. I. Chernoburova, M. A. Shchetinina, N. G. Kolotyrkina, A. S. Shashkov, Russ. Chem. Bull. (Int. Ed.), 2013, 62, 2626.
P. Patel, P. S. Patel, Int. J. Adv. Res. Chem. Sci. (IJARCS), 2015, 2, 25.
J. Dolezel, P. Hirsova, V. Opletalova, J. Dohnal, V. Marcela, J. Kunes, J. Jampilek, Molecules, 2009, 14, 4197.
R. Bryk, B. Gold, A. Venugopal, J. Singh, R. Samy, K. Pupek, H. Cao, C. Popescu, M. Gurney, S. Hotha, J. Cherian, K. Rhee, L. Ly, P. J. Converse, S. Ehrt, O. Vandal, X. Jiang, J. Schneider, G. Lin, C. Nathan, Cell Host Microbe, 2008, 3, 137.
A. J. Russell, I. M. Westwood, M. H. J. Crawford, J. Robinson, A. Kawamura, C. Redfield, N. Laurieri, E. D. Lowe, S. G. Davies, E. Sim, Bioorg. Med. Chem., 2009, 17, 905.
A. S. Nikitina, Ph.D Thesis (Chemistry), N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, 2009 (in Russian).
V. N. Yarovenko, A. S. Nikitina, I. V. Zavarzin, M. M. Krayushkin, L. V. Kovalenko, Synthesis, 2006, 8, 1246.
K. Ramkumar, V. N. Yarovenko, A. S. Nikitina, I. V. Zavarzin, M. M. Krayushkin, L. V. Kovalenko, A. Esqueda, S. Odde, N. Neamati, Molecules, 2010, 15, 3958.
V. N. Yarovenko, A. S. Nikitina, I. V. Zavarzin, M. M. Krayushkin, L. V. Kovalenko, Russ. Chem. Bull. (Int. Ed.), 2007, 56, 1624.
V. N. Yarovenko, A. S. Nikitina, I. V. Zavarzin, M. M. Krayushkin, L. V. Kovalenko, Russ. J. Org. Chem., 2007, 43, 1364.
V. N. Yarovenko, A. S. Nikitina, E. S. Zayakin, I. V. Zavarzin, M. M. Krayushkin, L. V. Kovalenko, ARKIVOC, 2008, ix, 103.
A. V. Komkov, A. S. Komendantova, L. G. Menchikov, E. I. Chernoburova, Y. A. Volkova, I. V. Zavarzin, Org. Lett., 2015, 17, 3734.
Y. A. Volkova, Y. S. Antonov, A. V. Komkov, A. M. Shcherbakov, A. S. Shashkov, L. G. Menchikov, E. I. Chernoburova, I. V. Zavarzin, RSC Adv., 2016, 6, 42863.
Ya. S. Antonov, Ph.D Thesis (Chemistry), N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, 2013 (in Russian).
T. S. Jagodzinski, Chem. Rev., 2003, 103, 197.
J. Wei, X. Jiang, Y. Li, Org. Lett., 2016, 18, 340.
A. P. Ranskii, A. G. Panasyuk, I. V. Markova, N. P. Bezverkhnii, L. I. Shebitchenko, Voprosy Khim. Khim. Tekhnol., 2008, 5, 9 (in Russian).
G. A. Gazieva, A. N. Kravchenko, Russ. Chem. Rev., 2012, 81, 494.
H. Wang, L. Wang, J. Shang, X. Li, H. Wang, J. Gui, A. Lei, Chem. Commun., 2012, 48, 76.
A. Wesołowska, Ł. Groś, S. Westerlich, T. S. Jagodziński, ARKIVOC, 2008, xv, 239.
A. O. Gálvez, C. P. Schaack, H. Noda, J. W. Bode, J. Am. Chem. Soc., 2017, 139, 1826.
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Published in Russian in Izyestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1143–1163, June, 2019.
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Krayushkin, M.M., Yarovenko, V.N. & Zavarzin, I.V. Synthesis of heterocyclic compounds based on oxamic acid monothiooxamides and thiohydrazides. Russ Chem Bull 68, 1143–1163 (2019). https://doi.org/10.1007/s11172-019-2533-0
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DOI: https://doi.org/10.1007/s11172-019-2533-0