CC BY 4.0 · Synthesis 2020; 52(02): 159-188
DOI: 10.1055/s-0039-1690688
review
Copyright with the author(s) (2019) The author(s)

Isothiazoles in the Design and Synthesis of Biologically Active Substances and Ligands for Metal Complexes

a  Organic Chemistry Department, Faculty of Science, Peoples’ Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St., Moscow 117198, Russian Federation   Email: [email protected]
,
Nikolay A. Bumagin
b  M.V. Lomonosov Moscow State University, Leninskii Gory, 1/3, Moscow 119991, Russian Federation   Email: [email protected]
,
a  Organic Chemistry Department, Faculty of Science, Peoples’ Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St., Moscow 117198, Russian Federation   Email: [email protected]
,
Dmitry G. Grudinin
a  Organic Chemistry Department, Faculty of Science, Peoples’ Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St., Moscow 117198, Russian Federation   Email: [email protected]
,
Vladimir I. Potkin
c  Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus, Surganova Str., 13, 220072, Minsk, Belarus   Email: [email protected]
› Author Affiliations
The publication has been prepared with the support of the "RUDN University Program 5-100".
Further Information

Publication History

Received: 21 July 2019

Accepted after revision: 09 September 2019

Publication Date:
17 October 2019 (online)


Abstract

The chemistry of isothiazoles is being intensively developed, which is evidenced by the wide range of selective transformations involving the isothiazole heterocycle and the high biological activity of its derivatives that can be used as effective new drugs and plant protection chemicals. Some representatives of isothiazoles have proven to be synergists of bioactive substances, which opens the way to lower the doses of drugs used and is especially important in cancer chemotherapy. In the framework of the present review, the accomplishments in the chemistry of isothiazoles over the past 18 years are examined, whilst current strategies for the synthesis of isothiazole-containing molecules and key directions of studies in this field of heterocyclic chemistry are discussed. Considerable attention is paid to chlorinated isothiazoles and strategies for their use in the synthesis of biologically active substances. In addition, a comprehensive review of existing literature in the field of metal complexes of isothiazoles is given, including the results and prospects for the practical use of isothiazole–metal complexes as catalysts for cross-coupling reactions in aqueous and aqueous–alcoholic media (‘green chemistry’).

1 Introduction

2 Synthesis by Ring-Forming Reactions

2.1 Intramolecular Cyclization

2.2 (4+1)-Heterocyclization

2.3 (3+2)-Heterocyclization

2.4 Syntheses by Ring Transformations

3 Isothiazoles by Ring Functionalization Reactions: Nucleophilic Substitution, Cross-Coupling and Side-Chain Functionalization

4 Selected Syntheses of Biologically Active Isothiazole Derivatives

5 Isothiazoles in the Synthesis of Transition-Metal Complexes and in Metal-Complex Catalysis

6 Conclusion

 
  • References

  • 1 Devys M, Barbier M, Loiselet I, Rouxel T, Sarniguet A, Kollmann A, Bousquet J.-F. Tetrahedron Lett. 1988; 29 , 6447
  • 2 Soledade M, Pedras C, Smith KC. Phytochemistry 1997; 46: 833
  • 3 Nakae K, Adachi H, Sawa R, Hosokawa N, Hatano M, Igarashi M, Nishimura Y, Akamatsu Y, Nomoto A. J. Nat. Prod. 2013; 76: 510
  • 4 Stratmann K, Belli J, Jensen CM, Moore RE, Patterson GM. L. J. Org. Chem. 1994; 59, 6279
  • 5 Garozzo A, Stivala A, Tempera G, Castro A. Antiviral Res. 2010; 88: 325
  • 6 Banerjee A, Yadav PS, Bajpai M, Sangana RR, Gullapalli S, Gudi GS, Gharat LA. Bioorg. Med. Chem. Lett. 2012; 22: 3223
  • 7 Lippa B, Morris J, Corbett M, Kwan TA, Noe MC, Snow SL, Gant TG, Mangiaracina M, Coffey HA, Foster B, Knauth EA, Wessel MD. Bioorg. Med. Chem. Lett. 2006; 16: 3444
  • 8 Carlessi L, Buscemi G, Larson G, Hong Z, Wu JZ, Delia D. Mol. Cancer Ther. 2007; 6: 935
  • 9 Coffey K, Blackburn TJ, Cook S, Golding BT, Griffin RJ, Hardcastle IR, Hewitt L, Huberman K, McNeill HV, Newell DR, Roche C, Ryan-Munden CA, Watson A, Robson CN. PLoS One 2012; 7: e45539
  • 10 Baerfacker L, Prechtl S, Siemeister G, Wengner AM, Ackerstaff J, Nowak-Reppel K, Bader B, Lienau P, Stoeckigt D. WO2014118186A1, 2014
  • 11 Ge Y. CN105254624A, 2016
  • 12 Ambati SR, Gudala S, Sharma A, Penta S, Reddy VL, Bomma Y, Janapala VR, Pola S. J. Heterocycl. Chem. 2017; 54: 2333
  • 13 Shintani Y, Niwa M, Monma S, Ishiyama S, Shigeta Y, Kamiyama T, Shimazawa Y, Okada K. WO2015170775A1, 2015
  • 14 Sui Z, Cai C, Zhang X. US20140275179A1, 2014
  • 15 Zhang X, Cai C, Sui Z, Macielag M, Wang Y, Yan W, Suckow A, Hua H, Bell A, Haug P, Clapper W, Jenkinson C, Gunnet J, Leonard J, Murray WV. ACS Med. Chem. Lett. 2017; 8: 947
  • 16 Bobbio C, Corsi C, Jeanmart SA. M, Wendeborn SV. WO2012010567A1, 2012
  • 17 Kudva N NU, Vicas CS, Murthy VS, Kotian SY, Byrappa K, Lokantha Rai KM. J. Chem., Biol. Phys. Sci. Sect. A 2016; 6: 861-868
  • 18 Kaizerman JA, Gross MI, Ge Y, White S, Hu W, Duan J.-X, Baird EE, Johnson KW, Tanaka RD, Moser HE, Burli RW. J. Med. Chem. 2003; 46: 3914
  • 19 Bürli RW, Ge Y, White S, Baird EE, Touami SM, Taylor M, Kaizerman JA, Moser HE. Bioorg. Med. Chem. Lett. 2002; 12: 2591
  • 20 Zhang Y. 104513213, 2015
  • 21 Liu G, Furuta K, Nakajima H, Ozoe F, Ozoe Y. Bioorg. Med. Chem. 2014; 22: 4637
  • 22 Corsi C, Wendeborn SV, Bobbio C, Kessabi J, Schneiter P, Grasso V, Haas UJ. WO2010069877A1, 2010
  • 23 Zong G.-N, Li F.-Y, Fan Z.-J, Mao W.-T, Song H.-B, Chen L, Zhu Y.-J, Xu J.-H, Song Y.-Q, Wang J.-R. Chin. J. Struct. Chem. 2015; 34: 871
  • 24 Wu Q.-F, Zhao B, Fan Z.-J, Zhao J.-B, Guo X.-F, Yang D.-Y, Zhang N.-L, Yu B, Kalinina T, Glukhareva T. RSC Adv. 2018; 8: 39593
  • 25 Bumagin NA, Potkin VI. Russ. Chem. Bull. 2016; 2: 321
  • 26 Potkin VI, Bumagin NA, Zelenkovskii VM, Petkevich SK, Zubenko YuS, Livantsov MV, Belov DS. Dokl. Natl. Acad. Sci. Belarus 2011; 55: 52
  • 27 Lider EV, Potkin VI, Lavrenova LG. Book of Abstracts, Sviridov Readings 2012, 6th International Conference on Chemistry and Chemical Education . Belarusian State University; Minsk/ Belarus: Apr 9–13, 2012; Publishing Center of BSU: Minsk, 2012, 72
  • 28 Chakroborty S, Bhanja C, Jena SA. Heterocycl. Commun. 2013; 19: 79
  • 29 Silva AM. S, Tomé AC, Pinho e Melo TM. V. D, Elguero J. Five-Membered Heterocycles: 1,2-Azoles. Part 2. Isoxazoles and Isothiazoles . In Modern Heterocyclic Chemistry, Vol. 2. Alvarez-Builla J, Jose Vaquero J, Barluenga J. Wiley-VCH; Weinheim: 2011: 727-808
  • 30 Wu Y.-J, Yang BV. Prog. Heterocycl. Chem. 2011; 22: 259
  • 31 Brown DW, Sainsbury M. Isothiazoles . In Hetarenes and Related Ring Systems: Science of Synthesis Category 2, Vol. 11. Schaumann E. Georg Thieme Verlag; Stuttgart: 2002: 507-572
  • 32 Kaberdin RV, Potkin VI. Russ. Chem. Rev. 2002; 71: 673
  • 33 Clerici F, Gelmi ML, Pellegrino S. Compr. Heterocycl. Chem. 2008; 4: 543
  • 34 Hamad Elgazwy A.-SS. Tetrahedron 2003; 59: 7445
  • 35 Clerici F, Gelmi ML, Pellegrino S, Pocar D. Top. Heterocycl. Chem. 2007; 9: 179
  • 36 Maienfisch P, Edmunds AJ. F. Adv. Heterocycl. Chem. 2017; 121: 35
  • 37 Schnürch F, Flasik R, Khan AF, Spina M, Mihovilovic MD, Stanetty P. Eur. J. Org. Chem. 2006; 3283
  • 38 Schulze B, Gidon D, Siegemund A, Rodina LL. Heterocycles 2003; 61: 639
  • 39 Hackler RE, Burow KW. Jr, Kaster SV, Wickiser DI. J. Heterocycl. Chem. 1989; 26: 1575
  • 40 Fisher MJ, Backer RT, Barth VN, Garbison KE, Gruber JM, Heinz BA, Iyengar S, Hollinshead SP, Kingston A, Kuklish SL, Li L, Nisenbaum ES, Peters SC, Phebus L, Simmons RM. A, van der Aar E. Bioorg. Med. Chem. Lett. 2012; 22: 2514
  • 41 Mishra M, Dutta Chowdhury SK, Mahalanabis KK. Synth. Commun. 2004; 34: 2681
  • 42 Yan S, Appleby T, Gunic E, Shim JH, Tasu T, Kim H, Rong F, Chen H, Hamatake R, Wu JZ, Hong Z, Yao N. Bioorg. Med. Chem. Lett. 2007; 17: 28
  • 43 Larson G, Yan S, Chen H, Rong F, Hong Z, Wu JZ. Bioorg. Med. Chem. Lett. 2007; 17: 172
  • 44 El Abdellaoui H, Varaprasad CV. N. S, Barawkar D, Chakravarty S, Maderna A, Tam R, Chen H, Allan M, Wu JZ, Appleby T, Yan S, Zhang W, Lang S, Yao N, Hamatake R, Hong Z. Bioorg. Med. Chem. Lett. 2006; 16: 5561
  • 45 Mishra M, Mahalanabis KK. ChemInform 2007; 38: 204
  • 46 Kiselyov AS, Semenova M, Semenov VV. Bioorg. Med. Chem. Lett. 2009; 19: 1195
  • 47 Tang Y, Zhu J, Sun T, Wang M, Ding J, Tian L, Zhu L, Hong C. CN103880774A, 2014
  • 48 Bardasov IN, Golubev RV, Ershov OV, Kayukov YS, Nasakin OE. Tetrahedron Lett. 2011; 52: 4724
  • 49 Degl’Innocenti A, Funicello M, Scafato P, Spagnolo P. Chem. Lett. 1994; 23: 1873
  • 50 Capperucci A, Degl’Innocenti A, Scafato P, Spagnolo P. Chem. Lett. 1995; 24: 147
  • 51 Konstantinova LS, Bastrakov MA, Starosotnikov AM, Glukhov IV, Lysov KA, Rakitin OA, Shevelev SA. Mendeleev Commun. 2010; 20: 353
  • 52 Abe T. WO2014054294A1, 2014
  • 53 Liu B.-B, Bai H.-W, Liu H, Wang S.-Y, Ji S.-J. J. Org. Chem. 2018; 83: 10281
  • 54 Shukla G, Srivastava A, Singh MS. Org. Lett. 2016; 18: 2451
  • 55 Soni S, Koley S, Singh MS. Tetrahedron Lett. 2017; 58: 2512
  • 56 Pedras MS. C, Suchy M. Bioorg. Med. Chem. 2006; 14: 714
  • 57 Scholz M, Ulbrich HK, Soehnlein O, Lindbom L, Mattern A, Dannhardt G. Bioorg. Med. Chem. 2009; 17: 558
  • 58 Amirhamzeh A, Vosoughi M, Shafiee A, Amini M. Med. Chem. Res. 2013; 22: 1212
  • 59 Zeng LF, Zhang H.-S, Wang Y.-H, Sanchez T, Zheng Y.-T, Neamatic N, Long Y.-Q. Bioorg. Med. Chem. Lett. 2008; 18: 4521
  • 60 Fordyce EA. F, Morrison AJ, Sharp RD, Paton RM. Tetrahedron 2010; 66: 7192
  • 61 Yanagida Y, Yazaki R, Kumagai N, Shibasaki M. Angew. Chem. Int. Ed. 2011; 50: 7910
  • 62 Clerici F, Contini A, Gelmi ML, Pocar D. Tetrahedron 2003; 59: 9399
  • 63 Amati M, Belviso S, D’Auria M, Lelj F, Racioppi R, Viggiani L. Eur. J. Org. Chem. 2010; 18: 3416
  • 64 Seo B, Kim YG, Lee PH. Org. Lett. 2016; 18: 5050
  • 65 Seo B, Kim H, Kim YG, Baek Y, Um K, Lee PH. J. Org. Chem. 2017; 82: 10574
  • 66 Kalogirou AS, Christoforou IC, Ioannidou HA, Manos MJ, Koutentis PA. RSC Adv. 2014; 4: 7735
  • 67 Chappell B, Dedman N, Wheeler S. Tetrahedron Lett. 2011; 52: 3223
  • 68 Zlotin SG, Kislitsyn PG, Lukjanov OA. Russ. Chem. Bull. 1998; 47: 534
  • 69 Nutaitis C. Top. Heterocycl. Chem. 2012; 29: 329
  • 70 Casoni A, Clerici F, Contini A, Pellegrino S, Sala A. Lett. Org. Chem. 2008; 5: 623
  • 71 Casoni A, Celentano G, Clerici F, Contini A, Gelmi ML, Mazzeo G, Pellegrino S, Rosini C. Tetrahedron: Asymmetry 2009; 20: 2247
  • 72 Christoforou IC, Koutentis PA, Rees CW. Org. Biomol. Chem. 2003; 1: 2900
  • 73 Ioannidou HA, Koutentis PA. Org. Lett. 2011; 13: 1510
  • 74 Kalogirou AS, Koutentis PA. Tetrahedron 2014; 70: 7092
  • 75 Potkin VI, Zubenko YuS, Petkevich SK. Russ. J. Org. Chem. 2008; 44: 1211
  • 76 Potkin VI, Nechai NI, Kaberdin RV. Russ. J. Org. Chem. 2007; 43: 587
  • 77 Zubenko YuS, Kletskov AV, Potkin VI, Zvereva TD, Zhukovskaya NA, Zolotar NM, Chepik OP. Proc. Natl. Acad. Sci. Belarus, Chem. Ser. 2011; 4: 53
  • 78 Zubenko Y, Potkin V. Synthesis 2009; 2361
  • 79 Nechai NI, Dikusar EA, Potkin VI, Kaberdin RV. Russ. J. Org. Chem. 2004; 40: 1050
  • 80 Potkin VI, Dikusar EA, Kletskov AV, Petkevich SK, Semenova EA, Kolesnik IA, Zvereva TD, Zhukovskaya NA, Rosentsveig IB, Levkovskaya GG, Zolotar RM. Russ. J. Gen. Chem. 2016; 86: 338
  • 81 Belykh DV, Malshakova MV, Kletskov AV, Ivanova ES, Dutikova YV, Potkin VI, Shtil AA. Macroheterocycles 2018; 11: 269
  • 82 Potkin VI, Petkevich SK, Zubenko YuS, Bykhovets AI. Russ. J. Org. Chem. 2007; 43: 1532
  • 83 Kletskov AV, Kolesnik IA, Dikusar EA, Zhukovskaya NA, Potkin VI. Russ. J. Gen. Chem. 2017; 87: 1167
  • 84 Potkin VI, Bykhovets AI, Kaberdin RV, Goncharuk VM, Nechai NI, Zolotar NM. BY 11556, 2009
  • 85 Potkin VI, Bykhovets AI, Nechai NI, Zolotar NM, Petkevich SK, Goncharuk VM. BY 11593, 2009
  • 86 Potkin VI, Bykhovets AI, Lahvich FA, Nechai NI, Zolotar NM, Goncharuk VM, Zubenko YuS, Vashkevich EV. BY 12039, 2009
  • 87 Petkevich SK, Dikusar EA, Kletskov AV. Rosentsveig I. B, Levkovskaya GG, Zolotar RM, Kurman PV, Potkin VI. Russ. J. Gen. Chem. 2018; 88: 234
  • 88 Vasilevskii DA, Galinovskii NA, Ol’Khovik VK, Golovchenko LA, Potkin VI, Kletskov AV. Russ. J. Org. Chem. 2014; 50: 1033
  • 89 Nikitin AY, Potkin VI, Bazanova LP, Levkovskaya GG, Petkevich SK, Kletskov AV. Disinfection Affairs 2014; 2: 23
  • 90 Potkin VI, Zubenko YuS. Russ. J. Org. Chem. 2009; 45: 568
  • 91 Potkin VI, Zubenko YuS, Nechai NI, Bykhovets AI, Kurman PV. Russ. J. Org. Chem. 2008; 44: 1038
  • 92 Zubenko YuS, Potkin VI, Bykhovets AI, Zolotar RM, Goncharuk VM. Proc. Natl. Acad. Sci. Belarus, Chem. Ser. 2009; 4: 94
  • 93 Potkin VI, Kletskov AV, Petkevich SK, Zubenko YS, Chotyanovich MO, Kulchitsky VA. Russ. J. Org. Chem. 2013; 49: 283
  • 94 Zubenko YS, Potkin VI, Bykhovets AI, Zolotar RM, Goncharuk VM. Dokl. Natl. Acad. Sci. Belarus 2012; 56: 69
  • 95 Potkin VI, Petkevich SK, Kletskov AV, Kolesnik IA, Dikusar EA, Rozentsveig IB, Levkovskaya GG, Nasirova DK, Borisova KK, Zubkov FI. Russ. J. Org. Chem. 2018; 54: 452
  • 96 Ioannidou HA, Koutentis PA. Tetrahedron 2009; 65: 7023
  • 97 Beebe JS, Jani JP, Knauth E, Goodwin P, Higdon C, Rossi AM, Emerson E, Finkelstein M, Floyd E, Harriman S, Atherton J, Hillerman S, Soderstrom C, Kou K, Gant T, Noe MC, Foster B, Rastinejad F, Marx MA, Schaeffer T, Whalen PM, Roberts WG. Cancer Res. 2003; 63: 7301
  • 98 Cohen RB, Langer CJ, Simon GR, Eisenberg PD, Hainsworth JD, Madajewicz S, Cosgriff TM, Pierce K, Xu H, Liau K, Healey D. Cancer Chemother. Pharmacol. 2007; 60: 81
  • 99 Luyten I, De Winter H, Busson R, Lescrinier T, Creuven I, Durant F, Balzarini J, De Clercq E, Herdewijn P. Helv. Chim. Acta 1996; 79: 1462
  • 100 Pasha FA, Muddassar M, Joo Cho S. Chem. Biol. Drug Des. 2009; 73: 292
  • 101 Reddy BM, Tanneeru K, Meetei PA, Guruprasad L. Chem. Biol. Drug Des. 2012; 79: 84
  • 102 Teffera Y, Choquette D, Liu J, Colletti AE, Hollis LS, Lin MH. J, Zhao Z. Chem. Res. Toxicol. 2010; 23: 1743
  • 103 Perrone MG, Vitale P, Malerba P, Altomare A, Rizzi R, Lavecchia A, Di Giovanni C, Novellino E, Scilimati A. ChemMedChem 2012; 7: 629
  • 104 McGregor DN, Corbin U, Swigor JE, Cheney LC. Tetrahedron 1969; 25: 389
  • 105 Hao J, Dehlinger V, Fivush AM, Rudyk HC. E, Britton TC, Hollinshead SP, Vokits BP, Clark BP, Henry SS, Massey SM, Peng L, Dressman B, Heinz BA, Roberts EF, Bracey-Walker MR, Swanson S, Catlow JT, Love PL, Tepool AD, Peters SC, Simmons RM, Iyengar S, McKinzie DL, Monn JA. Bioorg. Med. Chem. Lett. 2013; 23: 1249
  • 106 Britton TC, Dehlinger V, Fivush AM, Hollinshead SP, Vokits BP. WO2009123855A1, 2009
  • 107 Kiselyov AS, Semenova MN, Chernyshova NB, Leitao A, Samet AV, Kislyi KA, Raihstat MM, Oprea T, Lemcke H, Lantow M, Weiss DG, Ikizalp NN, Kuznetsov SA, Semenov VV. Eur. J. Med. Chem. 2010; 45: 1683
  • 108 Potkin VI, Zubenko Y, Bykhovetz A, Zolotar R, Goncharuk V. Nat. Prod. Commun. 2009; 4: 1205
  • 109 Potkin VI, Kletskov AV, Petkevich SK, Zubenko YS, Dikusar EA, Zvereva TD, Zolotar R, Chepik OP. Dokl. Natl. Acad. Sci. Belarus 2013; 57: 76
  • 110 Kletskov AV, Potkin VI, Dikusar EA, Zolotar RM. Nat. Prod. Commun. 2017; 12: 105
  • 111 Kletskov AV, Potkin VI, Kolesnik IA, Petkevich SK, Kvachonak AV, Dosina MO, Loiko DO, Larchenko MV, Pashkevich SG, Kulchitsky VA. Nat. Prod. Commun. 2018; 13: 1507
  • 112 Yu T, Tagat JR, Kerekes AD, Doll RJ, Zhang Y, Xiao Y, Esposite S, Belanger DB, Curran PJ, Mandal AK, Siddiqui M, Shih N, Basso A, Liu M, Gray K, Tevar S, Jones J, Lee S, Liang L, Ponery S, Smith E, Hruza A, Voigt J, Ramanathan L, Prosise W, Hu M. ACS Med. Chem. Lett. 2010; 1: 214
  • 113 Kulchitsky VA, Potkin VI, Zubenko YS, Chernov AN, Talabaev MV, Demidchik YE, Petkevich SK, Kazbanov VV, Gurinovich TA, Roeva MO, Grigoriev DG, Kletskov AV, Kalunov VN. Med. Chem. 2012; 8: 22
  • 114 Potkin VI, Petkevich SK, Kletskov AV, Zubenko YuS, Kurman PV, Pashkevich SG, Gurinovich TA, Kulchitskiy VA. Russ. J. Org. Chem. 2014; 50: 1667
  • 115 Potkin VI, Kletskov AV, Petkevich SK, Paschkevich SG, Kazbanov VV, Denisov AA, Kulchitsky VA. Heterocycl. Lett. 2015; 1: 11
  • 116 Sharma A, Suhas R, Gowda DC. Arch. Pharm. 2013; 346: 359
  • 117 Reddy KI, Srihari K, Renuka J, Sree KS, Chuppala A, Jeankumar VU, Sridevi JP, Babu KS, Yogeeswari P, Sriram D. Bioorg. Med. Chem. 2014; 22: 6552
  • 118 Ross JF, Delipala C, Watson MC, Crosby J, Paton RM. ARKIVOC 2013; (iii): 372
  • 119 Pedras MS. C, Jha M. J. Org. Chem. 2005; 70: 1828
  • 120 Bezbaruah P, Gogoi J, Rao KS, Gogoi P, Boruah RC. Tetrahedron Lett. 2012; 53: 4389
  • 121 Vicentini CB, Poli T, Manfrini M, Guarneri M, Giori P, Brandolini V. Farm. Ed. Sci. 1987; 42: 133
  • 122 Vicentini CB, Romagnoli C, Manfredini S, Rossi D, Mares D. Pharm. Biol. 2011; 49: 545
  • 123 Rossi D, Mares D, Romagnoli C, Andreotti E, Manfredini S, Vicentini CB. Drug Chem. Toxicol. 2011; 34: 324
  • 124 Koyioni M, Manoli M, Manolis MJ, Koutentis PA. J. Org. Chem. 2014; 79: 4025
  • 125 L’abbé G, D’hooge B, Dehaen W. J. Chem. Soc., Perkin Trans. 1 1995; 2379
  • 126 Rivest R, Weisz A. Can. J. Chem. 1971; 49: 1750
  • 127 Peach ME, Ramaswamy KK. Inorg. Chim. Acta 1971; 5: 445
  • 128 Sinha AI. P, Jain JL. J. Inorg. Nucl. Chem. 1981; 43: 3384
  • 129 Sinha AI. P, Jain JL, Sinha BK. Synth. React. Inorg. Met.-Org. Chem. 1984; 14: 151
  • 130 Sinha AI. P, Tewari SP, Sinha BK. Vijnana Parishad Anusandhan Patrika 1989; 32: 17
  • 131 Gruschinski S, Handke M, Kersting B. Z. Anorg. Allg. Chem. 2012; 638: 1274
  • 132 Kulig J, Lenarcik B. Pol. J. Chem. 1978; 52: 477
  • 133 Singh PP, Srivastava AK, Pathak LP. J. Coord. Chem. 1979; 9: 65
  • 134 Singh PP, Pathak LP, Srivastava SK. J. Inorg. Nucl. Chem. 1980; 42: 533
  • 135 Weis JC, Beck W. J. Organomet. Chem. 1972; 44: 325
  • 136 Pannell KH, Lee CC.-Y, Párkányi C, Redfearn R. Inorg. Chim. Acta 1975; 12: 127
  • 137 Hartshorn RM, Willis AC, Sargeson AM. J. Chem. Soc., Chem. Commun. 1988; 18: 1269
  • 138 Konrad M, Meyer F, Büchner M, Heinze K, Zsolnai L. Chem. Ber. 1997; 130: 95
  • 139 Potkin, V. I.; Lavrenova, L. G.; Lider, E. V.; Petkevich, S. K.; Zubenko, Y. S.; Kletskov, A. V.; Zolotar, R.; Timofeeva, V. A.; Golovchenko, L. A.; Book of Abstracts, 25th International Сhugaev Conference on Coordination Chemistry, Suzdal, Russia, Jun 6–11, 2011; ‘Ivanovo’ Publishing: Russia, 2011, 398.
  • 140 Lider, E. V.; Ikorskij, V. N.; Potapov, A. S.; Khlebnikov, A. I.; Zubenko, Y. S.; Potkin, V. I.; Lavrenova, L. G.; Book of Abstracts, 24th International Сhugaev Conference on Coordination Chemistry, St. Petersburg, Russia, Jun 15–19, 2009; Russkij Zapad; ISBN 5-85263-026-8: St. Petersburg, 2009, 103.
  • 141 Potkin VI, Kletskov AV, Lider EV, Lavrenova LG, Zolotar R. Dokl. Natl. Acad. Sci. Belarus 2016; 60: 86
  • 142 King AO, Yasuda N. Palladium-Catalyzed Cross-Coupling Reactions in the Synthesis of Phrmaceuticals. In Topics in Organometallic Chemistry, Vol. 6. Larsen RD. Springer-Verlag; Berlin: 2004: 205-245
  • 143 Lightowler S, Hird M. Chem. Mater. 2004; 16: 3963
  • 144 Johansson Seechurn CC. C, Kitching MO, Colacot TJ, Snieckus V. Angew. Chem. Int. Ed. 2012; 51: 5062
  • 145 Bellina F, Carpita A, Rossi R. Synthesis 2004; 2419
  • 146 Yin L, Liebscher J. Chem. Rev. 2007; 107: 133
  • 147 Polshettiwar V, Decottignies A, Len C, Fihri A. ChemSusChem 2010; 3: 502
  • 148 Chatterjee A, Ward TR. Catal. Lett. 2016; 146: 820
  • 149 Potkin VI, Bumagin SK, Petkevich SK, Kletskov AV, Zubenko YS, Golantsov NE, Livantsov MV, Belov DS, Veselov IS. Dokl. Natl. Acad. Sci. Belarus 2013; 57: 67
  • 150 Bumagin NA, Petkevich SK, Kletskov AV, Livantsov MV, Golantsov NE, Potkin VI. Chem. Heterocycl. Compd. 2013; 10: 1633
  • 151 Bumagin NA, Petkevich SK, Kletskov AV, Potkin VI. Chem. Heterocycl. Compd. 2017; 53: 1340
  • 152 Kletskov AV, Bumagin NA, Petkevich SK, Zvereva NA, Zhukovskaya PV, Kurman PV, Potkin VI. Proc. Natl. Acad. Sci. Belarus, Chem. Ser. 2015; 2: 54
  • 153 Bumagin NA, Zelenkovskii VM, Kletskov AV, Petkevich SK, Dikusar EA, Potkin VI. Russ. J. Gen. Chem. 2016; 86: 68
  • 154 Bumagin NA, Dikusar EA, Kletskov AV, Petkevich SK, Potkin VI. Proc. Natl. Acad. Sci. Belarus, Chem. Ser. 2015; 4: 34
  • 155 Frija LM. T, Pombeiro AJ. L, Kopylovich MN. Coord. Chem. Rev. 2016; 308: 32