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Synthesis 2019; 51(21): 4034-4042
DOI: 10.1055/s-0037-1611901
DOI: 10.1055/s-0037-1611901
paper
Combining Amines and 3-(2-Pyridyl)-[1,2,3]Triazolo[1,5-a]pyridine: An Easy Access to New Functional Polynitrogenated Ligands
This work was financially supported by the Ministerio de Economia, Industria y Competitividad (CONSOLIDER CTQ2017-90852-REDC), Generalitat Valenciana (Prometeo/2015/002) and the Universitat de València (Spain) (UV-INV-AE 15-332846).Further Information
Publication History
Received: 22 May 2019
Accepted after revision: 03 July 2019
Publication Date:
07 August 2019 (online)
Abstract
Triazolopyridine-pyridine amine ligands are easily obtained by means of either thermal- or copper(II)-mediated reactions. Starting from a readily accessible iodo derivative of triazolopyridine-pyridine and different amines, this new family of compounds combines aromatic and aliphatic nitrogen atoms with promising coordinating properties. Furthermore, chemical derivatization of a new triazolopyridine-pyridine diamine compound, N1-[6-([1,2,3]triazolo[1,5-a]pyridin-3-yl)pyridin-2-yl]ethan-1,2-diamine, allows the preparation of several remote-pyridine-containing ligands.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1611901.
- Supporting Information
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References
- 1a Wang B, Anslyn EV. Chemosensors: Principles, Strategies, and Applications . John Wiley & Sons; Hoboken: 2011
- 1b Bowman-James K, Bianchi A, Garcia-España E. Anion Coordination Chemistry . Wiley-VCH; Weinheim: 2012
- 2 Lehn JM. Supramolecular Chemistry, Concepts and Perspectives. Wiley-VCH; Weinheim: 1995
- 3a de Meijere A, Diederich F. Metal-Catalyzed Cross-Coupling Reactions . Wiley-VCH; Weinheim: 2008
- 3b Nishihara Y. Applied Cross-Coupling Reactions . Springer; Heidelberg: 2013
- 4 Joule JA, Mills K. Heterocyclic Chemistry, 4th ed. Blackwell Publishing; Oxford: 2000: 21
- 5 Abarca B, Ballesteros-Garrido R. 1,2,3-Triazoles Fused to Aromatic Rings. In Chemistry of 1,2,3-Triazoles - Topics in Heterocyclic Chemistry 40. Dehaen W, Bakulev VA. Springer; Heidelberg: 2015. 325
- 6a Bataglia LP, Carcelli M, Ferraro F, Mavilla L, Pelizzi C, Pelizzi G. J. Chem. Soc., Dalton Trans. 1994; 2615
- 6b Abarca B, Ballesteros R, Elmasnaouy M. Tetrahedron 1998; 54: 15287
- 7a Reddington E, Sapienza A, Gurau B, Viswanathan R, Sarangapani S, Smotk ES, Mallouk TE. Science 1998; 280: 1735
- 7b Abarca B, Aucejo R, Ballesteros R, Blanco F, García-España E. Tetrahedron Lett. 2006; 47: 8101
- 7c Ballesteros-Garrido R, Abarca B, Ballesteros R, Ramírez de Arellano C, Leroux FR, Colobert F, García-España E. New J. Chem. 2009; 33: 2102
- 7d Ballesteros-Garrido R, Delgado-Pinar E, Abarca B, Ballesteros R, Leroux FR, Colobert F, Zaragozá RJ, García-España E. Tetrahedron 2012; 68: 3701
- 7e Ballesteros-Garrido R, Abarca B, Ballesteros R, Colobert F, Leroux FR, García-España E. RSC Adv. 2015; 5: 29809
- 7f Cabrero-Antonino M, Ballesteros-Garrido R, Chiassai L, Escrivá E, Ramírez de Arellano C, Ballesteros R, Abarca B. New J. Chem. 2017; 41: 4918
- 7g Chiassai L, Ballesteros-Garrido R, Ballesteros R, Abarca B. New J. Chem. 2018; 42: 14597
- 8a Niel V, Gaspar AB, Muñoz MC, Abarca B, Ballesteros R, Real JA. Inorg. Chem. 2003; 42: 4782
- 8b Sheu C.-F, Chen K, Chen S.-M, Wen Y.-S, Lee G.-H, Chen J.-M, Lee J.-F, Cheng B.-M, Sheu H.-S, Yasuda N, Ozawa Y, Toriumi K, Wang Y. Chem. Eur. J. 2009; 15: 2384
- 8c Ramirez de Arellano C, Escriva E, Gomez-Garcia CJ, Minguez-Espallargas G, Ballesteros R, Abarca B. CrystEngComm 2013; 15: 1836
- 8d Arcis-Castillo Z, Pineiro-Lopez L, Munoz MC, Ballesteros R, Abarca B, Real JA. CrystEngComm 2013; 15: 3455
- 9a Chuprakov S, Hwang FW, Gevorgyan V. Angew. Chem. Int. Ed. 2007; 46: 4757
- 9b Chuprakov S, Gevorgyan V. Org. Lett. 2007; 9: 4463
- 9c Helan V, Gulevich AV, Gevorgyan V. Chem. Sci. 2015; 6: 1928
- 9d Shi Y, Gevorgyan V. Chem. Commun. 2015; 51: 17166
- 9e Chattopadhyay B, Gevorgyan V. Angew. Chem. Int. Ed. 2012; 51: 862
- 10 Shen R, Dong C, Yang J, Han L.-B. Adv. Synth. Catal. 2018; 360: 1
- 11 Abarca B, Ballesteros R, Jones G, Mojarrad F. Tetrahedron Lett. 1986; 27: 3543
- 12a Ullmann F, Bielecki J. Ber. Dtsch. Chem. Ges. 1901; 34: 2174
- 12b Ullmann F. Ber. Dtsch. Chem. Ges. 1904; 37: 853
- 12c Goldberg I. Ber. Dtsch. Chem. Ges. 1906; 39: 1691
- 12d Guram AS, Buchwald SL. J. Am. Chem. Soc. 1994; 116: 7901
- 12e Paul F, Patt J, Hartwig JF. J. Am. Chem. Soc. 1994; 116: 5969
- 12f Li JJ, Gribble G. Palladium in Heterocyclic Chemistry: A Guide for the Synthetic Chemist, Tetrahedron Organic Chemistry Series, Vol. 20. Pergamon, Amsterdam; 2000:
- 13 Abarca B, Alkorta I, Ballesteros R, Blanco F, Chadlaoui M, Elguero J, Mojarrad F. Org. Biomol. Chem. 2005; 3: 3905
- 14 Komori T, Satoh N, Yokoshima S, Fukuyama T. Synlett 2011; 1859
- 15a Zhang H, Cai Q, Ma D. J. Org. Chem. 2005; 70: 5164
- 15b Jiao J, Zhang XR, Chang NH, Wang J, Wei JF, Shi XY, Chen ZG. J. Org. Chem. 2011; 76: 1180
- 16 Jullian S, Fernández-Sandoval M, Rojas-Aranguiz H, Gómez-Machuca P, Salgado-Figueroa C, Celis-Barros G, Zapata-Torres G, Adam R, Abarca B. Carbohydr. Polym. 2014; 107: 124
- 17 Horner O, Girerd J.-J, Philouze C, Tchertanov L. Inorg. Chim. Acta 1999; 290: 139C
For the Ullmann–Goldberg reaction, see:
For the Buchwald–Hartwig cross-coupling reaction, see:
More specifically, the aryl halide amination reactions have been described by: