Synthesis of 2-Azidomethyl-5-ethynylfuran: A New Bio-Derived Self-Clickable Building Block

Bogdan Ya. Karlinskii; Leonid V. Romashov; Konstantin I. Galkin; Pavel G. Kislitsyn; Valentine P. Ananikov

doi:10.1055/s-0037-1610414

Synthesis, Table of Contents

CC BY ND NC 4.0 · Synthesis 2019; 51(05): 1235-1242
DOI: 10.1055/s-0037-1610414

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Synthesis of 2-Azidomethyl-5-ethynylfuran: A New Bio-Derived Self-Clickable Building Block

Bogdan Ya. Karlinskii

,

Leonid V. Romashov

,

Konstantin I. Galkin

,

Pavel G. Kislitsyn

,

Valentine P. Ananikov *

N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, Leninsky prospect 47, Moscow, 119991, Russian Federation Email: val@ioc.ac.ru

› Author Affiliations

Abstract

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Published as part of the 50 Years SYNTHESIS – Golden Anniversary Issue

Abstract

2-Azidomethyl-5-ethynylfuran, a new ambivalent compound with both azide and alkyne moieties that can be used as a self-clickable monomer, is synthesized starting directly from renewable biomass. The reactivity of the azide group linked to furfural is tested via the efficient preparation of a broad range of furfural-containing triazoles in good to excellent yields using a ‘green’ copper(I)-catalyzed azide–alkyne cycloaddition procedure. Access to new bio-based chemicals and oligomeric materials via a click-chemistry approach is also demonstrated using this bio-derived building block.

Key words

5-(hydroxymethyl)furfural - click chemistry - biomass conversion - triazoles - oligomers

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References

References

1a van Putten RJ, van der Waal JC, de Jong E, Rasrendra CB, Heeres HJ, de Vries JG. Chem. Rev. 2013; 113: 1499
1b Kucherov FA, Romashov LV, Galkin KI, Ananikov VP. ACS Sustainable Chem. Eng. 2018; 6: 8064
1c Sheldon RA. Green Chem. 2014; 16: 950
1d Teong SP, Yi G, Zhang Y. Green Chem. 2014; 16: 2015
1e Wang T, Nolte MW, Shanks BH. Green Chem. 2014; 16: 548
1f Delidovich I, Leonhard K, Palkovits R. Energy Environ. Sci. 2014; 7: 2803
1g Besson M, Gallezot P, Pinel C. Chem. Rev. 2013; 114: 1827
1h Yu IK. M, Tsang DC. W. Bioresour. Technol. 2017; 238: 716

2 Tong X, Ma Y, Li Y. Appl. Catal., A 2010; 385: 1

3a Roman-Leshkov Y, Barrett CJ, Liu ZY, Dumesic JA. Nature 2007; 447: 982
3b Saha B, Bohn CM, Abu-Omar MM. ChemSusChem 2014; 7: 3095
3c Hu L, Zhao G, Hao W, Tang X, Sun Y, Lin L, Liu S. RSC Adv. 2012; 2: 11184
3d Yang P, Xia Q, Liu X, Wang Y. Fuel 2017; 187: 159

4a Delidovich I, Hausoul PJ, Deng L, Pfutzenreuter R, Rose M, Palkovits R. Chem. Rev. 2016; 116: 1540
4b Davis ME. Top. Catal. 2015; 58: 405
4c Papageorgiou GZ, Papageorgiou DG, Terzopoulou Z, Bikiaris DN. Eur. Polym. J. 2016; 83: 202
4d Kucherov FA, Gordeev EG, Kashin AS, Ananikov VP. Angew. Chem. Int. Ed. 2017; 56: 15931

5a Nakagawa Y, Tamura M, Tomishige K. ACS Catal. 2013; 3: 2655
5b Herbst A, Janiak C. CrystEngComm 2017; 19: 4092
5c Rojas-Buzo S, García-García P, Corma A. Green Chem. 2018; 20: 3081
5d Fang R, Tian P, Yang X, Luque R, Li Y. Chem. Sci. 2018; 9: 1854
5e Romashov LV, Ananikov VP. Org. Biomol. Chem. 2016; 14: 10593

6 A literature survey was carried out using SciFinder and Reaxys (November 2018).
7 Huisgen R. Angew. Chem., Int. Ed. Engl. 1963; 2: 565

8a Rostovtsev VV, Green LG, Fokin VV, Sharpless KB. Angew. Chem. Int. Ed. 2002; 41: 2596
8b Kolb HC, Finn MG, Sharpless KB. Angew. Chem. Int. Ed. 2001; 40: 2004

9a Hawker CJ, Wooley KL. Science 2005; 309: 1200
9b Oakdale JS, Kwisnek L, Fokin VV. Macromolecules 2016; 49: 4473

10a Kolb HC, Sharpless KB. Drug Discovery Today 2003; 8: 1128
10b Wang Q, Chan TR, Hilgraf R, Fokin VV, Sharpless KB, Finn MG. J. Am. Chem. Soc. 2003; 125: 3192

11a Moses JE, Moorhouse AD. Chem. Soc. Rev. 2007; 36: 1249
11b Topchiy M, Ageshina A, Gribanov P, Masoud S, Akmalov T, Nefedov S, Osipov S, Nechaev M, Asachenko A. Eur. J. Org. Chem. 2018;

12 Romashov LV, Ananikov VP. Chem. Asian J. 2017; 12: 2652
13 Dunbabin A, Subrizi F, Ward JM, Sheppard TD, Hailes HC. Green Chem. 2017; 19: 397

For example, see:

14a Pruet JM, Saito R, Manzano LA, Jasheway KR, Wiget PA, Kamat I, Anslyn EV, Robertus JD. ACS Med. Chem. Lett. 2012; 3: 588
14b Goswami PP, Suding VP, Carlson AS, Topczewski JJ. Eur. J. Org. Chem. 2016; 4805
14c Pramanik S, Ghorai P. RSC Adv. 2013; 3: 23157
14d Kazancioglu EA, Kazancioglu MZ, Fistikci M, Secen H, Altundas R. Org. Lett. 2013; 15: 4790
14e Padwa A, Crawford KR, Rashatasakhon P, Rose M. J. Org. Chem. 2003; 68: 2609
14f Fabbro C, Armani S, Carloni L.-E, De Leo F, Wouters J, Bonifazi D. Eur. J. Org. Chem. 2014; 5487
14g Yakushijin K, Suzuki R, Kawaguchi N, Tsuboi Y, Furukawa H. Chem. Pharm. Bull. 1986; 34: 2049
14h Mascal M, Dutta S. Green Chem. 2011; 13: 40
14i Saikachi H, Kitagawa T. Chem. Pharm. Bull. 1978; 26: 1054

15a Nishida M, Fujii S, Aoki T, Hayakawa Y, Muramatsu H, Morita T. J. Fluorine Chem. 1990; 46: 445
15b Dominguez C, Csaky AG, Plumet J, Rigal L, Tauler C. Synth. Commun. 1991; 21: 1251
15c Carpita A, Rossi R, Veracini CA. Tetrahedron 1985; 41: 1919

16a Rogers SA, Melander C. Angew. Chem. Int. Ed. 2008; 47: 5229
16b Kim WJ, Korthals KA, Li S, Le C, Kalisiak J, Sharpless KB, Fokin VV, Miyamoto Y, Eckmann L. Antimicrob. Agents Chemother. 2017; 61: e02397-16
16c Ciardiello JJ, Stewart HL, Sore HF, Galloway W, Spring DR. Bioorg. Med. Chem. 2017; 25: 2825
16d Menendez C, Rodriguez F, Ribeiro AL, Zara F, Frongia C, Lobjois V, Saffon N, Pasca MR, Lherbet C, Baltas M. Eur. J. Med. Chem. 2013; 69: 167
16e Menendez C, Gau S, Ladeira S, Lherbet C, Baltas M. Eur. J. Org. Chem. 2012; 409
16f Nawratil S, Grypioti M, Menendez C, Mallet-Ladeira S, Lherbet C, Baltas M. Eur. J. Org. Chem. 2014; 654
16g Kumar R, Verma D, Mobin SM, Namboothiri IN. Org. Lett. 2012; 14: 4070
16h Yamamoto K, Bruun T, Kim JY, Zhang L, Lautens M. Org. Lett. 2016; 18: 2644
16i Kudryavtseva TN, Lamanov AY, Klimova LG, Nazarov GV. Russ. J. Gen. Chem. 2018; 88: 676

17 Zhang S, Xu Z, Gao C, Ren QC, Chang L, Lv ZS, Feng LS. Eur. J. Med. Chem. 2017; 138: 501

18a Kalhor-Monfared S, Beauvineau C, Scherman D, Girard C. Eur. J. Med. Chem. 2016; 122: 436
18b Dadmal TL, Appalanaidu K, Kumbhare RM, Mondal T, Ramaiah MJ, Bhadra MP. New J. Chem. 2018; 15546

19 Polymer Chemistry Series: Click Polymerization . Qin A, Tang BZ. The Royal Society of Chemistry; Cambridge: 2018
20 Galkin KI, Krivodaeva EA, Romashov LV, Zalesskiy SS, Kachala VV, Burykina JV, Ananikov VP. Angew. Chem. Int. Ed. 2016; 55: 8338
21 Mascal M, Nikitin EB. Angew. Chem. Int. Ed. 2008; 47: 7924
22 Armarego WL. F. Purification of Laboratory Chemicals . Butterworth-Heinemann; Oxford: 2017. 8th ed
23 Molander GA, Cadoret F. Tetrahedron Lett. 2011; 52: 2199
24 Shi E, Pei C. Synthesis 2004; 2995
25 Wijtmans M, de Graaf C, de Kloe G, Istyastono EP, Smit J, Lim H, Boonnak R, Nijmeijer S, Smits RA, Jongejan A, Zuiderveld O, de Esch IJ. P, Leurs R. J. Med. Chem. 2011; 54: 1693

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