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Improved method for the obtaining DTTA-appended 2,2’-bipyridine ligands for lanthanide cations

Dmitry S. Kopchuk, Alexey P. Krinochkin, Мaria I. Valieva, Еkaterina S. Starnovskaya, Yaroslav K. Shtaitz, Svetlana S. Rybakova, Evgeny D. Ladin, Ekaterina A. Kudryashova, Elvira R. Sharafieva, Оleg N. Chupakhin

Abstract


The composition of the reaction mixture after DTTA tert-butyl ester alkylation with 6'-halomethyl-5-phenyl-2,2'-bipyridines was studied. In addition to the target product, DTTA-appended 2,2’-bipyridine, the corresponding 6'-hydroxymethyl-substituted 2,2’-bipyridine and (5'-phenyl-[2,2'-bipyridin]-6-yl)methyl formate were isolated as by-products in some cases. Finally, an improved procedure for the DTTA tert-butyl ester alkylation with 6'-halomethyl-5-phenyl-2,2'-bipyridines by using Finkelstein reaction was developed.

Keywords


DTTA tert-butyl ester; 2,2'-bipyridines; Finkelstein reaction; ligands for lanthanide cations; alkylation

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References


Constable EC, Housecrof CE. The Early Years of 2,2’-bipyridine – a ligand in its own lifetime. Mol. 2019;24(21):3951. doi:10.3390/molecules24213951

Constable EC, Housecrof CE. Halide ion embraces in tris(2,2′-bipyridine)metal complexes. Cryst. 2020;10(8):1–16. doi:10.3390/cryst10080671

Cross JP, Dadabhoy A, Sammes PG. The sensitivity of the Lehn cryptand-europium and terbium (III) complexes to anions compared to a coordinatively saturated systems. J Lumin. 2004;110:113–124. doi:10.1016/J.JLUMIN.2004.05.004

Quici S, Marzanni G, Cavazzini M, Anelli PL, Botta M, Gia-nolio E, Accorsi G, Armaroli N, Barigelletti F. Highly lumi-nescent Eu(3+) and Tb(3+) macrocyclic complexes bearing an appended phenanthroline chromophore. Inorg Chem. 2002;41(10):2777–2784. doi:10.1021/ic025543j

Montgomery CP, Newa EJ, Palssona LO, Parker D, Batsanov AS, Lamarque L. Emissive and Cell-Permeable 3-Pyridyl- and 3-Pyrazolyl-4-azaxanthone lanthanide complexes and their behaviour in cellulo. Helv Chim Acta. 2009;92(11):2186–2213. doi:10.1002/hlca.200900122

Prokhorov AM, Kozhevnikov VN, Kopchuk DS, Bernard H, Le Bris N, Tripier R, Handel H, Koenig B, Kozhevnikov DN. 1,2,4-Triazine method of bipyridine ligand synthesis for the preparation of new luminescent Eu(III) complexes. Tetra-hedron. 2011;67:597–607. doi:10.1016/J.TET.2010.11.058

Armelao L, Quici S, Barigelletti F, Accorsi G, Bottaro G, Cavazzini M, Tondello E. Coord Chem Rev. 2010;254:487–505. doi:10.1016/j.ccr.2009.07.025

Krinochkin AP, Kopchuk DS, Kim GA, Ganebnykh IN, Ko-valev IS, Zyryanov GV, Li F, Rusinov VL, Chupakhin ON. DTTA-appended 6-phenyl- and 5,6-diphenyl-2,2′-bipyridines as new water soluble ligands for lanthanide cations. Polyhedron. 2017;134:59–64. doi:10.1016/j.poly.2017.05.030

Krinochkin AP, Kopchuk DS, Kim GA, Gorbunov EB, Kovalev IS, Santra S, Zyryanov GV, Majee A, Rusinov VL, Chupakhin ON. Synthesis and luminescence of new water-soluble lan-thanide complexes of DTTA-containing 4-(4-methoxyphenyl)-2,2'-bipyridine. Inorg Chim Acta. 2018;478:49–53. doi:10.1016/j.ica.2018.03.016

Krinochkin AP, Kopchuk DS, Kim GA, Ganebnykh IN, Ko-valev IS, Santra S, Zyryanov GV, Majee A, Rusinov VL, Chupakhin ON. Highly-luminescent DTTA-appended water-soluble lanthanide complexes of 4-(Het)aryl-2,2’-bipyridines: synthesis and photophysical properties. Chem Sel. 2019;4(20):6377–6381. doi:10.1002/slct.201901080

Krinochkin AP, Kopchuk DS, Kim GA, Shevyrin VA, Egorov IN, Santra S, Nosova EV, Zyryanov GV, Chupakhin ON, Cha-rushin VN. Highly-luminescent DTTA-appended lanthanide complexes of 4-(multi)fluoroaryl-2,2’-bipyridines: synthe-sis and photophysical studies. Polyhedron. 2021;195:114963. doi:10.1016/j.poly.2020.114962

Krinochkin AP, Kopchuk DS, Kim GA, Shevyrin VA, Santra S, Rahman M, Taniya OS, Zyryanov GV, Rusinov VL, Chupakhin ON. Water-soluble luminescent lanthanide complexes based on C6-DTTA-appended 5-aryl-2,2′-bipyridines. Polyhedron. 2020;181:114473. doi:10.1016/j.poly.2020.114473

Kopchuk DS, Pavlyuk DE, Kovalev IS, Zyryanov GV, Rusinov VL, Chupakhin ON. Synthesis of a new DTTA- and 5-phenyl-2,2'-bipyridine-based ditopic ligand and its Eu3+ complex. Can J Chem. 2016;94(7):599–603. doi:10.1139/cjc-2015-0576

Platzek J, Niedballa U, Radeuchel B, inventors; Shering AG, assignee. Process for the production of DTPA-tetraesters of terminal carboxylic acids. United States patent US5514810A. 1996, Jun 7.

Shaffer CL, Morton MD, Hanzlik RP. N-dealkylation of an N-cyclopropylamine by horseradish peroxidase. Fate of the cyclopropyl group. J Am Chem Soc. 2001;123(35):8502–8508. doi:10.1021/ja0111479

Wissner A, Carroll ML, Johnson BD, Kerwar SS, Pickett WC, Schaub RE, Torley LW, Trova MP, Kohler CA. Analogs of platelet activating factor. 6. Mono- and bis-aryl phosphate antagonists of platelet activating factor. J Med Chem. 1992;32(9):1650–1662. doi:10.1021/jm00087a023

Finkelstein H. Darstellung organischer jodide aus den entsprechenden bromiden und chloriden. Ber Dtsch Chem Ges. 1910;43(2):1528–1532. doi:10.1002/cber.19100430257




DOI: https://doi.org/10.15826/chimtech.2022.9.2.10

Copyright (c) 2022 Dmitry S. Kopchuk, Alexey P. Krinochkin, Мaria I. Valieva, Еkaterina S. Starnovskaya, Yaroslav K. Shtaitz, Svetlana S. Rybakova, Evgeny D. Ladin, Ekaterina A. Kudryashova, Elvira R. Sharafieva, Оleg N. Chupakhin

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Chimica Techno Acta, 2014-2023
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