Synthesis 2020; 52(13): 1874-1896
DOI: 10.1055/s-0039-1690858
short review
© Georg Thieme Verlag Stuttgart · New York

5-Iodo-1H-1,2,3-triazoles as Versatile Building Blocks

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Institute of Chemistry, Saint Petersburg State University (SPbU), Universitetskaya nab. 7/9, 199034 Saint Petersburg, Russian Federation   Email: [email protected]
› Author Affiliations
This study was supported by the Russian Science Foundation (19-73-10077).
Further Information

Publication History

Received: 20 December 2019

Accepted after revision: 26 February 2020

Publication Date:
14 April 2020 (online)


Abstract

Copper-catalyzed azide–alkyne cycloaddition is a useful tool for the synthesis of both 1,2,3-triazoles and 5-iodo-1H-1,2,3-triazoles starting from either terminal alkynes or iodoalkynes. 5-Iodotriazoles have been recognized as very useful building blocks for the synthesis of diverse 1,4,5-trisubstituted 1,2,3-triazoles. Synthetic application of 5-iodo-1,2,3-triazoles through the creation of a new C–C, C–heteroatom, or C–D(T) bond along with the application areas of both iodotriazoles and products of their modification including radiolabeled compounds are discussed.

1 Introduction

2 Synthetic Approaches to 5-Iodo-1H-1,2,3-triazoles

3 5-Iodotriazoles in C–C Bond Formation

3.1 Intermolecular C–C Cross-Coupling

3.2 Intramolecular Cross-Coupling: Direct Arylation and C–I/C–I Homocoupling­

3.3 Other Transformations

4 5-Iodotriazoles in Radiolabeling, Halogen Exchange, and Heterocoupling Reactions

5 Summary

 
  • References

  • 1 Haldón E, Nicasio MC, Pérez PJ. Org. Biomol. Chem. 2015; 13: 9528
  • 2 Neumann S, Biewend M, Rana S, Binder WH. Macromol. Rapid Commun. 2019; 41: 1900359
  • 3 Johansson JR, Beke-Somfai T, Said Stålsmeden A, Kann N. Chem. Rev. 2016; 116: 14726
  • 4 Harris T, Alabugin IV. Mendeleev Commun. 2019; 29: 237
  • 5 Dommerholt J, Rutjes FP. J. T, van Delft FL. Top. Curr. Chem. 2016; 374: 16
  • 6 Jalani HB, Karagöz A. Ç, Tsogoeva SB. Synthesis 2017; 49: 29
  • 7 Ahmed M, Razaq H, Faisal M, Siyal AN, Haider A. Synth. Commun. 2017; 47: 1193
  • 8 Wei F, Wang W, Ma Y, Tung C.-H, Xu Z. Chem. Commun. 2016; 52: 14188
  • 9 Chen Z, Liu Z, Cao G, Li H, Ren H. Adv. Synth. Catal. 2017; 359: 202
  • 10 Li L, Zhang Z. Molecules 2016; 21: 1393
  • 11 Prasher P, Sharma M. MedChemComm 2019; 10: 1302
  • 12 Dheer D, Singh V, Shankar R. Bioorg. Chem. 2017; 71: 30
  • 13 Bonandi E, Christodoulou MS, Fumagalli G, Perdicchia D, Rastelli G, Passarella D. Drug Discovery Today 2017; 22: 1572
  • 14 Zhang S, Xu Z, Gao C, Ren QC, Chang L, Lv ZS, Feng LS. Eur. J. Med. Chem. 2017; 138: 501
  • 15 Gao P, Sun L, Zhou J, Li X, Zhan P, Liu X. Expert Opin. Drug Discovery 2016; 11: 857
  • 16 Song MX, Deng XQ. J. Enzyme Inhib. Med. Chem. 2018; 33: 453
  • 17 Huo J, Hu H, Zhang M, Hu X, Chen M, Chen D, Liu J, Xiao G, Wang Y, Wen Z. RSC Adv. 2017; 7: 2281
  • 18 Döhler D, Michael P, Binder WH. Acc. Chem. Res. 2017; 50: 2610
  • 19 Van Hilst QV. C, Lagesse NR, Preston D, Crowley JD. Dalton Trans. 2018; 47: 997
  • 20 Vasdev RA. S, Preston D, Crowley JD. Dalton Trans. 2017; 46: 2402
  • 21 Scattergood PA, Elliott PI. P. Dalton Trans. 2017; 46: 16343
  • 22 Zurro M, Mancheño OG. Chem. Rec. 2017; 17: 485
  • 23 Hein JE, Fokin VV. Chem. Soc. Rev. 2010; 39: 1302
  • 24 Shealy YF, O’Dell CA. J. Med. Chem. 1966; 9: 733
  • 25 Shafran YM, Bakulev VA, Mokrushin VS, Alekseev SG. Chem. Heterocycl. Compd. 1984; 20: 1038
  • 26 Kuijpers BH. M, Dijkmans GC. T, Groothuys S, Quaedflieg PJ. L. M, Blaauw RH, van Delft FL, Rutjes FP. J. T. Synlett 2005; 3059
  • 27 Hein JE, Tripp JC, Krasnova LB, Sharpless KB, Fokin VV. Angew. Chem. Int. Ed. 2009; 48: 8018
  • 28 Kilah NL, Wise MD, Serpell CJ, Thompson AL, White NG, Christensen KE, Beer PD. J. Am. Chem. Soc. 2010; 132: 11893
  • 29 Kaasik M, Metsala A, Kaabel S, Kriis K, Järving I, Kanger T. J. Org. Chem. 2019; 84: 4294
  • 30 Borissov A, Marques I, Lim JY. C, Félix V, Smith MD, Beer PD. J. Am. Chem. Soc. 2019; 141: 4119
  • 31 Lim JY. C, Beer PD. Eur. J. Org. Chem. 2019; 2019: 3433
  • 32 Klein HA, Beer PD. Chem. Eur. J. 2019; 25: 3125
  • 33 Kaasik M, Kaabel S, Kriis K, Järving I, Kanger T. Synthesis 2019; 51: 2128
  • 34 Bunchuay T, Docker A, Martinez-Martinez AJ, Beer PD. Angew. Chem. Int. Ed. 2019; 58: 13823
  • 35 Peterson A, Kaasik M, Metsala A, Järving I, Adamson J, Kanger T. RSC Adv. 2019; 9: 11718
  • 36 Wu Y.-M, Deng J, Li Y, Chen Q.-Y. Synthesis 2005; 1314
  • 37 Li L, Zhang G, Zhu A. J. Org. Chem. 2008; 73: 3630
  • 38 Paper F, Li L, Li Y, Li R, Zhu A, Zhang G. Aust. J. Chem. 2011; 64: 1383
  • 39 Li L, Hao G, Zhu A, Liu S, Zhang G. Tetrahedron Lett. 2013; 54: 6057
  • 40 Huang Y, Zhang Y, Yuan Y, Cao W. Tetrahedron 2015; 71: 2124
  • 41 Lim JY. C, Bunchuay T, Beer PD. Chem. Eur. J. 2017; 23: 4700
  • 42 Klein HA, Kuhn H, Beer PD. Chem. Commun. 2019; 55: 9975
  • 43 Mayooufi A, Romdhani-Younes M, Carcenac Y, Thibonnet J. Synth. Commun. 2019; 49: 2168
  • 44 Yan R, Sander K, Galante E, Rajkumar V, Badar A, Robson M, El-Emir E, Lythgoe MF, Pedley RB, Årstad E. J. Am. Chem. Soc. 2013; 135: 703
  • 45 Gao F, Peng C, Li J, Zhuang R, Guo Z, Xu D, Su X, Zhang X. J. Labelled Compd. Radiopharm. 2019; 62: 301
  • 46 Goyard D, Chajistamatiou AS, Sotiropoulou AI, Chrysina ED, Praly J.-P, Vidal S. Chem. Eur. J. 2014; 20: 5423
  • 47 Smith NW, Polenz BP, Johnson SB, Dzyuba SV. Tetrahedron Lett. 2010; 51: 550
  • 48 Goyard D, Praly J, Vidal S. Carbohydr. Res. 2012; 362: 79
  • 49 Juríček M, Stout K, Kouwer PH. J, Rowan AE. Org. Lett. 2011; 13: 3494
  • 50 Juríček M, Stout K, Kouwer PH. J, Rowan AE. J. Porphyrins Phthalocyanines 2011; 15: 898
  • 51 Schneider G, Görbe T, Mernyák E, Wölfling J, Holczbauer T, Czugler M, Sohár P, Minorics R, Zupkó I. Steroids 2015; 98: 153
  • 52 Hottin A, Scandolera A, Duca L, Wright DW, Davies GJ, Behr J. Bioorg. Med. Chem. Lett. 2016; 26: 1546
  • 53 Zhong Z, Du C, Luo Z, Song S, Liao G, Yao J, Goldmann S, Wang Z. Org. Process Res. Dev. 2017; 21: 1371
  • 54 Ostrowski T, Zeidler J. Nucleic Acids Symp. Ser. 2008; 52: 585
  • 55 Ostrowski T, Januszczyk P, Cieslak M, Kazmierczak-Baranska J, Nawrot B, Bartoszak-Adamska E, Zeidler J. Bioorg. Med. Chem. 2011; 19: 4386
  • 56 Joubert N, Schinazi RF, Agrofoglio LA. Tetrahedron 2005; 61: 11744
  • 57 Dinér P, Andersson T, Kjellén J, Elbing K, Hohmann S, Grøtli M. New J. Chem. 2009; 33: 1010
  • 58 Tepper R, Schulze B, Jäger M, Friebe C, Scharf DH, Görls H, Schubert US. J. Org. Chem. 2015; 80: 3139
  • 59 Dubrovina NV, Domke L, Shuklov IA, Spannenberg A, Franke R, Villinger A, Börner A. Tetrahedron 2013; 69: 8809
  • 60 Lim JY. C, Cunningham MJ, Davis JJ, Beer PD. Chem. Commun. 2015; 51: 14640
  • 61 Tepper R, Schulze B, Görls H, Bellstedt P, Jäger M, Schubert US. Org. Lett. 2015; 17: 5740
  • 62 Giraudo A, Krall J, Nielsen B, Sørensen TE, Kongstad KT, Rolando B, Boschi D, Frølund B, Lolli ML. Eur. J. Med. Chem. 2018; 158: 311
  • 63 Ahmed N, Konduru NK, Ahmad S, Owais M. Eur. J. Med. Chem. 2014; 82: 552
  • 64 Brotherton WS, Clark RJ, Zhu L. J. Org. Chem. 2012; 77: 6443
  • 65 Barsoum D, Brassard C, Deeb J, Okashah N, Sreenath K, Simmons J, Zhu L. Synthesis 2013; 45: 2372
  • 66 Zhu L, Brassard CJ, Zhang X, Guha PM, Clark RJ. Chem. Rec. 2016; 16: 1501
  • 67 Berg R, Straub BF. Beilstein J. Org. Chem. 2013; 9: 2715
  • 68 Barsoum DN, Okashah N, Zhang X, Zhu L. J. Org. Chem. 2015; 80: 9542
  • 69 Chung R, Vo A, Fokin VV, Hein JE. ACS Catal. 2018; 8: 7889
  • 70 Zhang J, Chen W, Wang B, Zhao Z, Wang X, Hu Y. RSC Adv. 2015; 5: 14561
  • 71 Chung R, Vo A, Hein JE. ACS Catal. 2017; 7: 2505
  • 72 Larin EM, Lautens M. Angew. Chem. Int. Ed. 2019; 58: 13438
  • 73 Lal S, Rzepa HS, Díez-González S. ACS Catal. 2014; 4: 2274
  • 74 Silva PJ, Bernardo CE. P. J. Phys. Chem. A 2018; 122: 7497
  • 75 Ito S, Satoh A, Nagatomi Y, Hirata Y, Suzuki G, Kimura T, Satow A, Maehara S, Hikichi H, Hata M, Kawamoto H, Ohta H. Bioorg. Med. Chem. 2008; 16: 9817
  • 76 Darwish A, Blacker M, Janzen N, Rathmann SM, Czorny S, Hillier SM, Joyal JL, Babich JW, Valliant JF. ACS Med. Chem. Lett. 2012; 3: 313
  • 77 Edem PE, Czorny S, Valliant JF. J. Med. Chem. 2014; 57: 9564
  • 78 Huang J, Macdonald SJ. F, Harrity JP. A. Chem. Commun. 2009; 436
  • 79 Oakdale JS, Sit RK, Fokin VV. Chem. Eur. J. 2014; 20: 11101
  • 80 Zhang L, Chen X, Xue P, Sun HH. Y, Williams ID, Sharpless KB, Fokin VV, Jia G. J. Am. Chem. Soc. 2005; 127: 15998
  • 81 Gribanov PS, Chesnokov GA, Topchiy MA, Asachenko AF, Nechaev MS. Org. Biomol. Chem. 2017; 15: 9575
  • 82 Gribanov PS, Chesnokov GA, Dzhevakov PB, Kirilenko NY, Rzhevskiy SA, Ageshina AA, Topchiy MA, Bermeshev MV, Asachenko AF, Nechaev MS. Mendeleev Commun. 2019; 29: 147
  • 83 Papudippu M, Shu H, Izenwasser S, Wade D, Gulasey G, Fournet S, Stevens ED, Lomenzo SA, Trudell ML. Med. Chem. Res. 2012; 21: 4473
  • 84 Abarca B, Aucejo R, Ballesteros R, Blanco F, García-España E. Tetrahedron Lett. 2006; 47: 8101
  • 85 Fiandanese V, Maurantonio S, Punzi A, Rafaschieri GG. Org. Biomol. Chem. 2012; 10: 1186
  • 86 Deng J, Wu Y.-M, Chen Q.-Y. Synthesis 2005; 2730
  • 87 Voltrová S, Putovný I, Matoušek V, Klepetářová B, Beier P. Eur. J. Org. Chem. 2018; 2018: 5087
  • 88 Blastik ZE, Voltrová S, Matoušek V, Jurásek B, Manley DW, Klepetářová B, Beier P. Angew. Chem. Int. Ed. 2017; 56: 346
  • 89 Voltrová S, Muselli M, Filgas J, Matoušek V, Klepetářová B, Beier P. Org. Biomol. Chem. 2017; 15: 4962
  • 90 Thiery E, You V, Mora A, Abarbri M. Eur. J. Org. Chem. 2016; 2016: 529
  • 91 Fehér K, Gömöry Á, Skoda-Földes R. Monatsh. Chem. 2015; 146: 1455
  • 92 Yousuf M, Mukherjee D, Dey S, Pal C, Adhikari S. Eur. J. Med. Chem. 2016; 124: 468
  • 93 Aizpurua JM, Azcune I, Fratila RM, Balentova E, Sagartzazu-Aizpurua M, Miranda JI. Org. Lett. 2010; 12: 1584
  • 94 Deobald A, Camargo L, Hörner M, Rodrigues O, Alves D, Braga A. Synthesis 2011; 2397
  • 95 De Simone R, Chini MG, Bruno I, Riccio R, Mueller D, Werz O, Bifulco G. J. Med. Chem. 2011; 54: 1565
  • 96 Dheer D, Rawal RK, Singh V, Sangwan PL, Das P, Shankar R. Tetrahedron 2017; 73: 4295
  • 97 Li L, Xing X, Zhang C, Zhu A, Fan X, Chen C, Zhang G. Tetrahedron Lett. 2018; 59: 3563
  • 98 Carcenac Y, David-Quillot F, Abarbri M, Duchêne A, Thibonnet J. Synthesis 2013; 45: 633
  • 99 Govdi AI, Danilkina NA, Ponomarev AV, Balova IA. J. Org. Chem. 2019; 84: 1925
  • 100 Bogdan AR, James K. Org. Lett. 2011; 13: 4060
  • 101 Nie F, Kunciw DL, Wilcke D, Stokes JE, Galloway WR. J. D, Bartlett S, Sore HF, Spring DR. Angew. Chem. Int. Ed. 2016; 55: 11139
  • 102 Schwartz E, Breitenkamp K, Fokin VV. Macromolecules 2011; 44: 4735
  • 103 Andrews KT, Fisher GM, Sumanadasa SD. M, Skinner-Adams T, Moeker J, Lopez M, Poulsen S.-A. Bioorg. Med. Chem. Lett. 2013; 23: 6114
  • 104 Morris JC, Chiche J, Grellier C, Lopez M, Bornaghi LF, Maresca A, Supuran CT, Pouysségur J, Poulsen S.-A. J. Med. Chem. 2011; 54: 6905
  • 105 Feng J, He H, Zhou Y, Guo X, Liu H, Cai M, Wang F, Feng L, He H. Bioorg. Med. Chem. 2019; 27: 2413
  • 106 Dinér P, Veide Vilg J, Kjellén J, Migdal I, Andersson T, Gebbia M, Giaever G, Nislow C, Hohmann S, Wysocki R, Tamás MJ. Grøtli M. PLoS One 2011; 6: e20012
  • 107 Ingham OJ, Paranal RM, Smith WB, Escobar RA, Yueh H, Snyder T, Porco JA, Bradner JE, Beeler AB. ACS Med. Chem. Lett. 2016; 7: 929
  • 108 Piras M, Testa A, Fleming IN, Dall’Angelo S, Andriu A, Menta S, Mori M, Brown GD, Forster D, Williams KJ, Zanda M. ChemMedChem 2017; 12: 1142
  • 109 Piras M, Andriu A, Testa A, Wienecke P, Fleming I, Zanda M. Synlett 2017; 28: 2769
  • 110 Wu Q, Qu F, Wan J, Xia Y, Peng L. Nucleosides, Nucleotides Nucleic Acids 2005; 24: 999
  • 111 Krajczyk A, Zeidler J, Januszczyk P, Dawadi S, Boshoff HI, Barry CE, Ostrowski T, Aldrich CC. Bioorg. Med. Chem. 2016; 24: 3133
  • 112 Malnuit V, Duca M, Manout A, Bougrin K, Benhida R. Synlett 2009; 2123
  • 113 Amdouni H, Robert G, Driowya M, Furstoss N, Métier C, Dubois A, Dufies M, Zerhouni M, Orange F, Lacas-Gervais S, Bougrin K, Martin AR, Auberger P, Benhida R. J. Med. Chem. 2017; 60: 1523
  • 114 Donnier-Maréchal M, Vidal S. Expert Opin. Ther. Pat. 2016; 26: 199
  • 115 Sahoo L, Singhamahapatra A, Loganathan D. Org. Biomol. Chem. 2014; 12: 2615
  • 116 Fu D, Zhang J, Cao S. J. Fluorine Chem. 2013; 156: 170
  • 117 Kotovshchikov Y, Latyshev G, Beletskaya I, Lukashev N. Synthesis 2018; 50: 1926
  • 118 Barve IJ, Thikekar TU, Sun C.-M. Org. Lett. 2017; 19: 2370
  • 119 Szuroczki P, Sámson J, Kollár L. ChemistrySelect 2019; 4: 5527
  • 120 de Albuquerque DY, de Moraes JR, Schwab RS. Eur. J. Org. Chem. 2019; 2019: 6673
  • 121 Schulman JM, Friedman AA, Panteleev J, Lautens M. Chem. Commun. 2012; 48: 55
  • 122 Morgen M, Jöst C, Malz M, Janowski R, Niessing D, Klein CD, Gunkel N, Miller AK. ACS Chem. Biol. 2016; 11: 1001
  • 123 Panteleev J, Geyer K, Aguilar-Aguilar A, Wang L, Lautens M. Org. Lett. 2010; 12: 5092
  • 124 Guerrero I, Correa A. Eur. J. Org. Chem. 2018; 2018: 6034
  • 125 Irastorza A, Aizpurua JM, Correa A. Org. Lett. 2016; 18: 1080
  • 126 Wang H, Yi X, Cui Y, Chen W. Org. Biomol. Chem. 2018; 16: 8191
  • 127 Michaels HA, Simmons JT, Clark RJ, Zhu L. J. Org. Chem. 2013; 78: 5038
  • 128 Adam MJ, Wilbur DS. Chem. Soc. Rev. 2005; 34: 153
  • 129 Yan R, El-emir E, Rajkumar V, Robson M, Jathoul AP, Pedley RB, Årstad E. Angew. Chem. Int. Ed. 2011; 50: 6793
  • 130 Zhang W, Fan W, Zhou Z, Garrison J. ACS Med. Chem. Lett. 2017; 8: 1269
  • 131 Genady AR, Janzen N, Banevicius L, El-Gamal M, El-Zaria ME, Valliant JF. J. Med. Chem. 2016; 59: 2660
  • 132 Worrell BT, Hein JE, Fokin VV. Angew. Chem. Int. Ed. 2012; 51: 11791
  • 133 Wang D, Sun W, Chu T. Eur. J. Org. Chem. 2015; 2015: 4114
  • 134 Paparella AS, Lee KJ, Hayes AJ, Feng J, Feng Z, Cini D, Deshmukh S, Booker GW, Wilce MC. J, Polyak SW, Abell AD. ACS Infect. Dis. 2018; 4: 175
  • 135 Testa A, Piras M, Hickey M, Fleming I, Bushby N, Lenz E, Elmore C, Zanda M. Synlett 2014; 25: 1019
  • 136 Testa A, Dall’Angelo S, Mingarelli M, Augello A, Schweiger L, Welch A, Elmore CS, Sharma P, Zanda M. Bioorg. Med. Chem. 2017; 25: 963
  • 137 Wang D, Chen S, Wang J, Astruc D, Chen B. Tetrahedron 2016; 72: 6375
  • 138 Li L, Shang T, Ma X, Guo H, Zhu A, Zhang G. Synlett 2015; 26: 695
  • 139 do Nascimento JE. R, Gonçalves LC. C, Hooyberghs G, Van der Eycken EV, Alves D, Lenardão EJ, Perin G, Jacob RG. Tetrahedron Lett. 2016; 57: 4885
  • 140 Kotovshchikov YN, Latyshev GV, Navasardyan MA, Erzunov DA, Beletskaya IP, Lukashev NV. Org. Lett. 2018; 20: 4467
  • 141 Kiss A, Herman BE, Görbe T, Mernyák E, Molnár B, Wölfling J, Szécsi M, Schneider G. Steroids 2018; 135: 79