A convenient and simple method for the synthesis of bis(carboxymethyl)thioacetals and -thioketals starting from the corresponding mercaptocarboxylic acids and carbonyl compounds was developed. The obtained compounds were studied as potential sulfur-containing ligands for the preparation of mixed salts (complexes) with Co(II) and Zn(II).
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V. Yu. Kovtun, Yu. A. Davidovich, V. D. Gladkikh, et al., Khim.-farm. Zh., 54(11), 31 – 34 (2020); Pharm. Chem. J., 54(11), 1136 – 1139 (2021).
R. L. Shriner, J. M. Cross, and E. H. Bodratz, J. Am. Chem. Soc., 61, 2001 – 2003 (1939).
J. M. Bramlett, H.-J. Im, X.-H. Yu, et al., Inorg. Chim. Acta., 357(1), 243 – 249 (2004).
V. Farzaliyev, A. Shuriberko, A. Sujayev, et al., J. Mol. Struct., 1221, 128844 – 128853 (2020).
S. Ebrahimi and M. Sayadi, J. Sulfur Chem., 33, No. 6, 647 – 652 (2012).
B. Pooladian, E. Ghasemi, and Z. Karimi-Jaberi, Green Chem. Lett. Rev., 7(1), 60 – 63 (2014).
L. F. Tietze, T. Pfeiffer, and A. Schuffenhauer, Eur. J. Org. Chem., 12, 2733 – 2741 (1998).
M. P. Thakare, R. Shaikh, and D. Tayade, J. Sulfur Chem., 38(5), 465 – 475 (2017).
V. K. Rai, P. K. Rai, S. Bajaj, et al., Green Chem., 13(5), 1217 – 1223 (2011).
V. K. Rai, P. Tiku, and A. Kumar, Synth. Commun., 42(10), 1489 – 1499 (2012).
V. K. Rai and R. K. Kosta, Can. J. Chem., 94(10), 827 – 832 (2016).
L. D. S. Yadav, S. Yadav, and V. K. Rai, Tetrahedron, 61(42), 10013 – 10017 (2005).
L. D. S. Yadav, S. Singh, and V. K. Rai, Green Chem., 11(6), 878 – 882 (2009).
A. Dandia, V. Parewa, S. L. Gupta, et al, J. Mol. Catal. A: Chem., 373, 61 – 71 (2013).
M. Dewan, A. Kumar, A. Saxena, et al., Tetrahedron Lett., 51(47), 6108 – 6110 (2010).
W. Cunico, W. T. Vellasco Junior, M. Moreth, et al., Lett. Org. Chem., 5(5), 349 – 352 (2008).
S. Higashiya, S. Narizuka, A. Konno, et al., J. Org. Chem., 64(1), 133 – 137 (1999).
G. A. Kraus, J. Bae, and P. K. Choudhury, Synthesis, 1, 19 – 20 (2003).
M. Oya, T. Baba, E. Kato, et al., Chem. Pharm. Bull., 30(2), 440 – 461 (1982).
H. E. Howard-Lock, C. J. L. Lock, M. L. Martins, et al., Can. J. Chem., 64(6), 1215 – 1219 (1986).
O. B. Sutcliffe, R. C. Storr, T. L. Gilchrist, et al., J. Chem. Soc., Perkin Trans. 1, 15, 1795 – 1806 (2001).
Y. Koide, T. Hasegawa, A. Takahashi, et al., J. Med. Chem., 45(21), 4629 – 4638 (2002).
R. J. Reischl, W. Bicker, T. Keller, et al., Anal. Bioanal. Chem., 404(6 – 7), 1779 – 1787 (2012).
F. E. Onen-Bayram, K. Buran, I. Durmaz, et al., Med. Chem. Commun., 6(1), 90 – 93 (2014).
A. Yu. Ershov, I. V. Lagoda, D. G. Nasledov, et al., Russ. J. Org. Chem., 53(11), 1682 – 1686 (2017).
D. Bermejo-Velasco, G. N. Nawale, O. P. Oommen, et al., Chem. Commun., 54(88), 12507 – 12510 (2018).
G. E. Woodward and E. F. Schroeder, J. Am. Chem. Soc., 59, 1690 – 1694 (1937).
T. Shiraiwa, K. Kataoka, S. Sakata, et al., Bull. Chem. Soc. Jpn., 61(11), 4158 – 4160 (1988).
K. C. Nicolaou, M. Nevalainen, B. S. Safina, et al., Angew. Chem. Int. Ed., 41(11), 1941 – 1945 (2002).
K. Kantharaju, S. Raghothama, U. S. Raghavender, et al., Biopolymers (Peptide Science), 92(5), 405 – 416 (2009).
A. Sun, Y. J. Lu, H. Hu, et al., Bioorg. Med. Chem. Lett., 19(23), 6627 – 6631 (2009).
X. Lu and T. E. Long, Tetrahedron Lett., 52(39), 5051 – 5054 (2011).
T. Kubo, J. L. Swartz, G. M. Scheutz, et al., Macromol. Rapid Commun., 40(1), 1800590 – 1800595 (2018).
D. S. Kemp and R. I. Carey, J. Org. Chem., 54(15), 3640 – 3646 (1989).
D. Baba, H. Ishii, S. Higashiya, et al., J. Org. Chem., 66(21), 7020 – 7024 (2001).
H. Bagum, K. E. Christensen, M. Genov, et al, J. Org. Chem., 84(16), 10257 – 10279 (2019).
H. Bagum, K. E. Christensen, and M. Genov, Tetrahedron, 75(40), 130561 – 130582 (2019).
H. Bagum, B. R. Shire, K. E. Christensen, et al., Synlett, 31(4), 378 – 382 (2020).
Q. Meng, Y. Li, Y. He, et al., Tetrahedron: Asymmetry, 11(21), 4255 – 4261 (2000).
C. Starkenmann, J. Agric. Food Chem., 51(24), 7146 – 7155 (2003).
E. Pini, D. Nava, and R. Stradi, Org. Prep. Proced. Int., 36(2), 166 – 170 (2004).
C. Starkenmann, R. Brauchil, and B. M. Firmenich, J. Agric. Food Chem., 53(23), 9244 – 9248 (2005).
K. R. Hebditch, L. Nicolau, and M. A. Brimble, J. Labelled Compd. Radiopharm., 50(4), 237 – 243 (2007).
V. Mall, I. Sellami, and P. Schieberle, J. Agric. Food Chem., 66(42), 11083 – 11091 (2018).
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Translated from Khimiko-Farmatsevticheskii Zhurnal, Vol. 55, No. 5, pp. 48 – 50, May, 2021.
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Davidovich, Y.A., Kozlov, S.V. Reaction of Mercaptocarboxylic Acids with Carbonyl Compounds. Pharm Chem J 55, 506–509 (2021). https://doi.org/10.1007/s11094-021-02449-2
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DOI: https://doi.org/10.1007/s11094-021-02449-2