RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
CC BY-ND-NC 4.0 · Synthesis 2019; 51(05): 1235-1242
DOI: 10.1055/s-0037-1610414
DOI: 10.1055/s-0037-1610414
paper
Synthesis of 2-Azidomethyl-5-ethynylfuran: A New Bio-Derived Self-Clickable Building Block
This study was supported by a Russian Science Foundation 17-13-01176 grant.Weitere Informationen
Publikationsverlauf
Received: 05. Oktober 2018
Accepted after revision: 26. November 2018
Publikationsdatum:
08. Januar 2019 (online)
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.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610414.
- Supporting Information
-
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
- 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
For example, see: