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Synlett 2018; 29(20): 2685-2688
DOI: 10.1055/s-0037-1610323
DOI: 10.1055/s-0037-1610323
letter
Synthesis of 1,4-Disubstituted 1H-1,2,3-Triazoles from 4-(1-Adamantyl)benzyl Azide through a 1,3-Dipolar Cycloaddition Reaction
Thanks are due to the University of Aveiro and FCT/MCT (Portugal) for financial support to the QOPNA Research Unit (FCT UID/QUI/00062/2013) through national founds and, where applicable, co-finance by the FEDER, within the PT2020 Partnership Agreement, as well as to the Portuguese NMR Network. Thanks are also due to the Université des Frères Mentouri Constantine 1 for a Scholarship to O.B.H.Further Information
Publication History
Received: 14 October 2018
Accepted after revision: 15 October 2018
Publication Date:
21 November 2018 (online)
Abstract
A series of new 1,4-disubstituted 1H-1,2,3-triazole derivatives were synthesized by an efficient copper-catalyzed 1,3-dipolar cycloaddition reaction of 4-(1-adamantyl)benzyl azide with several terminal alkynes. The copper catalyst was used to provide 1,4-disubstituted 1,2,3-triazoles regioselectively in good yields.
Key words
triazoles - 1,3-dipolar cycloaddition - copper catalysis - one-pot process - adamantylbenzyl azide - click chemistrySupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610323.
- Supporting Information
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References and Notes
- 1 Demaray JA, Thuener JE, Dawson MN, Sucheck SJ. Bioorg. Med. Chem. Lett. 2008; 18: 4868
- 2 Wang X.-L, Wan K, Zhou C.-H. Eur. J. Med. Chem. 2010; 45: 4631
- 3 Banday AH, Shameem SA, Ganai BA. Org. Med. Chem. Lett. 2012; 2: 13
- 4 Pokhodylo N, Shyyka O, Matiychuk V. Med. Chem. Res. 2014; 23: 2426
- 5 Chandrashekhar M, Nayak VL, Ramakrishna S, Mallavadhani UV. Eur. J. Med. Chem. 2016; 114: 293
- 6 He Y.-W, Dong C.-Z, Zhao J.-Y, Ma L.-L, Li Y.-H, Aisa HA. Eur. J. Med. Chem. 2014; 76: 245
- 7 Whiting M, Tripp JC, Lin Y.-C, Lindstrom W, Olson AJ, Elder JH, Sharpless KB, Fokin VV. J. Med. Chem. 2006; 49: 7697
- 8 Buckle DR, Rockell CJ. M, Smith H, Spicer BA. J. Med. Chem. 1984; 27: 223
- 9 Shanmugavelan P, Nagarajan S, Sathishkumar M, Ponnuswamy A, Yogeeswari P, Sriram D. Bioorg. Med. Chem. Lett. 2011; 21: 7273
- 10 Costa MS, Boechat N, Rangel EA, da Silva F. deC, de Souza AM. T, Rodrigues CR, Castro HC, Júnior IN, Lourenço MC. S, Wardell SM. S. V, Ferreira V. Bioorg. Med. Chem. 2006; 14: 8644
- 11 Rajasekaran A, Rajagopal KA. Acta Pharm. (Warsaw, Pol.) 2009; 59: 355
- 12 De Simone R, Chini MG, Bruno I, Riccio R, Mueller D, Werz O, Bifulco G. J. Med. Chem. 2011; 54: 1565
- 13 Sharma P, Kumar A, Upadhyay S, Singh J, Sahu V. Med. Chem. Res. 2010; 19: 589
- 14 Singh BK, Yadav AK, Kumar B, Gaikwad A, Sinha SK, Chaturvedi V, Tripathi RP. Carbohydr. Chem. 2008; 343: 1153
- 15 Micetich RG, Maiti SN, Spevak P, Hall TW, Yamabe S, Ishida N, Tanaka M, Yamazaki T, Nakai A, Ogawa K. J. Med. Chem. 1987; 30: 1469
- 16 Actor P, Uri JV, Phillips L, Sachs CS, Zajac JR. G, Berges DA, Dunn GL, Hoover JR. E, Weisbach JA. J. Antibiot. 1975; 28: 594
- 17 Lamoureux G, Artavia G. Curr. Med. Chem. 2010; 17: 2967
- 18 Rostovtsev VV, Green LG, Fokin VV, Sharpless KB. Angew. Chem. Int. Ed. 2002; 41: 2596
- 19 Xie F, Sivakumar K, Zeng Q, Bruckman MA, Hodges B, Wang Q. Tetrahedron 2008; 64: 2906
- 20 Zheng Z.-J, Wang D, Xu Z, Xu L.-W. Beilstein J. Org. Chem. 2015; 11: 2557
- 21 Liu J, Obando D, Liao V, Lifa T, Codd R. Eur. J. Med. Chem. 2011; 46: 1949
- 22 Togo Y, Hornick RB, Dawkins AT. Jr. JAMA J. Am. Med. Assoc. 1968; 203: 1089
- 23 Zoidis G, Kolocouris N, Naesens E, De Clercq E. Bioorg. Med. Chem. 2009; 17: 1534
- 24 Van Derpoorten K, Balzarini J, De Clercq E, Poupaert JH. Biomed. Pharmacother. 1997; 51: 464
- 25 El-Emam AA, Al-Deeb OA, Al-Omar MA, Lehmann J. Bioorg. Med. Chem. 2004; 12: 5107
- 26 Abou-Gharbia MA, Childers WE. Jr, Fletcher H, McGaughey G, Patel U, Webb MB, Yardley J, Andree T, Boast C, Kuchark RJ. Jr, Marquis K, Morris H, Scerni R, Moyer JA. J. Med. Chem. 1999; 42: 5077
- 27 Owen JC. E, Whitton PS. Brain Res. 2006; 1117: 206
- 28 Omar K, Geronikaki A, Zoumpoulakis P, Camoutsis C, Soković M, Ćirić A, Glamočlija J. Bioorg. Med. Chem. 2010; 18: 426
- 29 Al-Omar MA, Al-Abdullah ES, Shehata IA, Habib EE, Ibrahim TM, El-Emam AA. Molecules 2010; 15: 2526
- 30a Mosset P, Grée R. Synlett 2013; 24: 1142
- 30b Ikunaka M, Maruoka K, Okuda Y, Ooi T. Org. Process Res. Dev. 2003; 7: 644
- 31 Cintas P, Barge A, Tagliapietra S, Boffa L, Cravatto G. Nat. Protoc. 2010; 5: 607
- 32 Click Synthesis of 1,2,3-Triazoles 5a–s: General Procedure Cu(OAc)2·H2O (24 mg, 0.1 equiv) and NaAsc (23 mg, 0.1 equiv) were added to a stirred solution of 4-(1-adamantyl)benzyl azide (3; 0.32 g, 1.2 mmol) and the appropriate terminal alkyne 4 (1.2 mmol) in DMF (5 mL). The mixture was then stirred for 2–3 h at r.t. until the starting material was completely consumed (TLC). Sat. brine was added to the mixture and the crude product was extracted with EtOAc (3 × 10 mL). The combined extracts were dried (Na2SO4), filtered, and concentrated in vacuo. The crude product was purified by flash column chromatography [silica gel, EtOAc–PE (1:3)].
- 33 {1-[4-(1-Adamantyl)benzyl]-1H-1,2,3-triazol-4-yl}methanol (5b) White solid; yield: 314 mg (81%); mp 168 °C. IR (run as NaCl discs): 3200, 1025, 2900, 2847 cm−1. 1H NMR: δ = 7.46 (s, 1 H, triazole-H), 7.39 (d, J = 8.4 Hz, 2 H, Ar-H), 7.26 (d, J = 8.3 Hz, 2 H, Ar-H), 5.48 (s, 2 H, CH2–N), 4.75 (s, 2 H, CH2–O), 2.80 (s, 1 H, OH), 2.09–2.17 (m, 3 H, ad-H), 1.92 (br d, 6 H, ad-H), 1.81–1.80 (m, 6 H, ad-H). 13C NMR: δ = 152.3 (Ar-Cq), 143.9 (triazole-Cq), 131.5 (1 C, Ar-Cq), 128.1, 125.8 (4 C, Ar-C), 121.7 (1 C, Ar-C), 120.2 (triazole-CH), 56.6 (CH2–O), 54.1 (s, CH2–N), 43.2 (3 C, CH2, ad-C), 36.8 (3 C, CH2, ad-C), 36.3 (ad-Cq), 28.9 (3 C, CH, ad-C). HRMS (ESI+): m/z [M + H]+ calcd for C20H26N3O: 324.2077; found: 324.2068.