Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2019; 51(23): 4487-4497
DOI: 10.1055/s-0037-1610726
DOI: 10.1055/s-0037-1610726
paper
Recyclable Heterogeneous Copper(II)-Catalyzed Oxidative Cyclization of 2-Pyridine Ketone Hydrazones Towards [1,2,3]Triazolo[1,5-a]pyridines
We thank the National Natural Science Foundation of China (No. 21462021), the Natural Science Foundation of Jiangxi Province of China (No. 20161BAB203086), and the Key Laboratory of Functional Small Organic Molecules, Ministry of Education (No. KLFS-KF-201704) for financial support.Further Information
Publication History
Received: 15 June 2019
Accepted after revision: 06 August 2019
Publication Date:
03 September 2019 (online)
Abstract
The heterogeneous copper(II)-catalyzed oxidative cyclization of 2-pyridine ketone hydrazones was achieved in ethyl acetate at room temperature in the presence of an MCM-41-anchored bidentate 2-aminoethylamino copper(II) catalyst [MCM-41-2N-Cu(OAc)2], in the presence of air as the oxidant, yielding a wide variety of [1,2,3]triazolo[1,5-a]pyridines in mostly good to high yields. The present method was also applied to the direct one-pot synthesis of [1,2,3]triazolo[1,5-a]pyridines from 2-acylpyridine derivatives and hydrazine monohydrate. Importantly, this supported copper(II) catalyst could be conveniently obtained via a simple procedure from easily available and inexpensive reagents, recovered by filtration of the reaction mixture, and reused at least seven times without a significant loss of catalytic activity.
Key words
copper catalysis - [1,2,3]triazolo[1,5-a]pyridines - oxidative cyclization - heterogeneous catalysis - N–N couplingSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610726.
- Supporting Information
-
References
- 1a Jones G. Adv. Heterocycl. Chem. 2002; 83: 1
- 1b Jones G, Abarca B. Adv. Heterocycl. Chem. 2010; 100: 195
- 2a Abarca B, Ballesteros R, Ballesteros-Garrido R, Colobert F, Leroux FR. Tetrahedron 2008; 64: 3794
- 2b Abarca B, Ballesteros R, Blanco F, Bouillon A, Collot V, Dominguez J.-R, Lancelot J.-C, Rault S. Tetrahedron 2004; 60: 4887
- 2c Abarca B, Ballesteros R, Chadlaoui M. Tetrahedron 2004; 60: 5785
- 2d Abarca B, Ballesteros R, Chadlaoui M, Miralles J, Murillo JV, Colonna D. Tetrahedron 2001; 57: 10111
- 2e Bentabed-Ababsa G, Blanco F, Derdour A, Mongin F, Trecourt F, Queguiner G, Ballesteros R, Abarca B. J. Org. Chem. 2009; 74: 163
- 2f Abarca B, Aucejo R, Ballesteros R, Blanco F, Garcia-Espana E. Tetrahedron Lett. 2006; 47: 8101
- 3 Abarca B, Adam R, Ballesteros R. ARKIVOC 2010; (iii): 319
- 4a Abarca B, Ballesteros R, Chadlaoui M, de Arellano CR, Real JA. Eur. J. Inorg. Chem. 2007; 4574
- 4b Ballesteros-Garrido R, Abarca B, Ballesteros R, de Arellano CR, Leroux FR, Colobert F, Garcia-Espana E. New J. Chem. 2009; 33: 2102
- 4c Chadlaoui M, Abarca B, Ballesteros R, de Arellano CR, Aguilar J, Aucejo R, Garcia-Espana E. J. Org. Chem. 2006; 71: 9030
- 4d Ballesteros-Garrido R, Delgado-Pinar E, Abarca B, Ballesteros R, Leroux FR, Colobert F, Zaragoza RJ, Garcia-Espana E. Tetrahedron 2012; 68: 3701
- 4e Niel V, Gaspar AB, Munoz MC, Abarca B, Ballesteros R, Real JA. Inorg. Chem. 2003; 42: 4782
- 4f 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
- 4g Mamula O, von Zelewsky A. Coord. Chem. Rev. 2003; 242: 87
- 4h Piguet C, Berbardinelli G, Hopfgartner G. Chem. Rev. 1997; 97: 2005
- 5a Chuprakov S, Hwang FW, Gevorgyan V. Angew. Chem. Int. Ed. 2007; 46: 4757
- 5b Liu S, Sawicki J, Driver TG. Org. Lett. 2012; 14: 3744
- 5c Shi Y, Gulevich AV, Gevorgyan V. Angew. Chem. Int. Ed. 2014; 53: 14191
- 5d Joshi A, Mohan DC, Adimurthy S. Org. Lett. 2016; 18: 464
- 5e Joshi A, Mohan DC, Adimurthy S. J. Org. Chem. 2016; 81: 9461
- 5f Kim H, Kim S, Kim J, Son J.-Y, Baek Y, Um K, Lee PH. Org. Lett. 2017; 19: 5677
- 6 Boyer JH, Borgers R, Wolford LT. J. Am. Chem. Soc. 1957; 79: 678
- 7a Ogura H, Mineo S, Nakagawa K, Shiba S. Yakugaku Zasshi 1981; 101: 329
- 7b Mineo S, Kawamura S, Nakagawa K. Synth. Commun. 1976; 6: 69
- 8 Maury G, Meziane D, Srairi D, Paugan J.-P, Paugam R. Bull. Soc. Chim. Belg. 1982; 91: 153
- 9a Zimmerman HE, Ignatchenko A. J. Org. Chem. 1999; 64: 6635
- 9b Escriva E, Server-Carrio J, Lezama L, Folgado JV, Pizarro JL, Ballesteros R, Abarca B. J. Chem. Soc. Dalton Trans. 1997; 2033
- 9c Abarca B, Alkorta I, Ballesteros R, Blanco F, Chadlaoui M, Elguero J, Mojarrad F. Org. Biomol. Chem. 2005; 3: 3905
- 10 Battaglia LP, Carcelli M, Ferraro F, Mavilla L, Pelizzi C, Pelizzi G. J. Chem. Soc., Dalton Trans. 1994; 2651
- 11a Prakash O, Gujral HK, Rani N, Singh SP. Synth. Commun. 2000; 30: 417
- 11b Wang K, Fu X, Liu J, Liang Y, Dong D. Org. Lett. 2009; 11: 1015
- 12a Borduas N, Powell DA. J. Org. Chem. 2008; 73: 7822
- 12b Boldron C, Gamez P, Tooke DM, Spek AL, Reedijk J. Angew. Chem. Int. Ed. 2005; 44: 3585
- 12c Li Z.-P, Li C.-J. J. Am. Chem. Soc. 2005; 127: 3672
- 12d Li Z.-P, Li C.-J. J. Am. Chem. Soc. 2005; 127: 6968
- 12e Basle O, Li C.-J. Green Chem. 2007; 9: 1047
- 12f Li C.-J. Acc. Chem. Res. 2009; 42: 335
- 12g Wendlandt AE, Suess AM, Stahl SS. Angew. Chem. Int. Ed. 2011; 50: 11062
- 13a Beletskaya IP, Chepakov AV. Coord. Chem. Rev. 2004; 248: 2337
- 13b Ley SV, Thomas AW. Angew. Chem. Int. Ed. 2003; 42: 5400
- 13c Chemler SR, Fuller PH. Chem. Soc. Rev. 2007; 36: 1153
- 13d Martin R, Rodriguez-Rivero M, Buchwald SL. Angew. Chem. Int. Ed. 2006; 45: 7079
- 13e Jones CP, Anderson KW, Buchwald SL. J. Org. Chem. 2007; 72: 7968
- 13f Rodriguez-Rivero M, Buchwald SL. Org. Lett. 2007; 9: 973
- 14a Allen SE, Walvoord RR, Padilla-Salinas R, Kozlowski MC. Chem. Rev. 2013; 113: 6234
- 14b Lin W, Hu M.-H, Feng X, Cao C.-P, Huang Z.-B, Shi D.-Q. Tetrahedron 2013; 69: 6721
- 14c Zhao M.-N, Liang H, Ren Z.-H, Guan Z.-H. Synthesis 2012; 44: 1501
- 14d Li J, Zhang Q, Zhou L. J. Org. Chem. 2012; 77: 2566
- 14e Bera S, Samanta K, Panda G. Tetrahedron Lett. 2011; 52: 3234
- 14f Thiel OR, Achmatowicz MM, Reichelt A, Larsen RD. Angew. Chem. Int. Ed. 2010; 49: 8395
- 14g Neumann JJ, Surt M, Glorius F. Angew. Chem. Int. Ed. 2010; 49: 7790
- 14h Monguchi Y, Hattori K, Maegawa T, Hirota K, Sajiki H. Heterocycles 2009; 79: 669
- 14i Correa A, Tellitu I, Dominguez E, SanMartin R. J. Org. Chem. 2006; 71: 3501
- 15a Suri M, Jousseaume T, Neumann JJ, Glorius F. Green Chem. 2012; 14: 2193
- 15b Zhang C, Jiao N. Angew. Chem. Int. Ed. 2010; 49: 6174
- 15c Mankad NP, Muller P, Peters JC. J. Am. Chem. Soc. 2010; 132: 4083
- 15d Guru MM, Tharmalingam P. J. Org. Chem. 2012; 77: 5063
- 16a Ueda S, Nagasawa H. J. Am. Chem. Soc. 2009; 131: 15080
- 16b Hirayama T, Ueda S, Okada T, Tsurue N, Okuda K, Nagasawa H. Chem. Eur. J. 2014; 20: 4156
- 17a Zhang J.-P, Lin Y.-Y, Huang X.-C, Chen X.-M. J. Am. Chem. Soc. 2005; 127: 5495
- 17b Klingele MH, Brooker S. Coord. Chem. Rev. 2003; 241: 119
- 17c Haasnoot JG. Coord. Chem. Rev. 2000; 200: 131
- 17d Klingele J, Kaase D, Hilgert J, Steinfeld G, Klingele MH, Lach J. Dalton Trans. 2010; 39: 4495
- 17e Wang D, Etienne L, Echeverria M, Moya S, Astruc D. Chem. Eur. J. 2014; 20: 4047
- 18a Girard C, Onen E, Aufort M, Beauviere S, Samson E, Herscovici J. Org. Lett. 2006; 8: 1689
- 18b Chassaing S, Sido AS. S, Alix A, Kumarraja M, Pale P, Sommer J. Chem. Eur. J. 2008; 14: 6713
- 18c Lipshutz BH, Taft BR. Angew. Chem. Int. Ed. 2006; 45: 8235
- 19a Chiang GC. H, Olsson T. Org. Lett. 2004; 6: 3079
- 19b Benyahya S, Monnier F, Taillefer M, Man MW. C, Bied C, Ouazzani F. Adv. Synth. Catal. 2008; 350: 2205
- 19c Benyahya S, Monnier F, Man MW. C, Bied C, Ouazzani F, Taillefer M. Green Chem. 2009; 11: 1121
- 19d Phan NT. S, Nguyen TT, Nguyen VT, Nguyen KD. ChemCatChem 2013; 5: 2374
- 19e Chouhan G. Wang D., Alper H. 2007; 4809
- 19f Zhao H, He W, Yao R, Cai M. Adv. Synth. Catal. 2014; 356: 3092
- 19g Zhao H, Jiang Y, Chen Q, Cai M. New J. Chem. 2015; 39: 2106
- 19h Zhao H, He W, Wei L, Cai M. Catal. Sci. Technol. 2016; 6: 1488
- 19i Xia J, Huang X, Cai M. Synthesis 2019; 51: 2014
- 19j Wei L, You S, Tuo Y, Cai M. Synthesis 2019; 51: 3091
- 19k Pan S, Yan S, Osako T, Uozumi Y. ACS Sustainable Chem. Eng. 2017; 5: 10722
- 20a Kresge CT, Leonowicz ME, Roth WJ, Vartuli JC, Beck JS. Nature 1992; 359: 710
- 20b Corma A. Top. Catal. 1997; 4: 249
- 20c Martin-Aranda RM, Cejka J. Top. Catal. 2010; 53: 141
- 21a Kantam ML, Bandyopadhyay T, Rahman A, Reddy NM, Choudary BM. J. Mol. Catal. A: Chem. 1998; 133: 293
- 21b Mehnert PC, Weaver DW, Ying JY. J. Am. Chem. Soc. 1998; 120: 12289
- 21c Mukhopadhyay K, Sarkar BR, Chaudhari RV. J. Am. Chem. Soc. 2002; 124: 9692
- 21d Tsai F.-Y, Lin B.-N, Chen M.-J, Mou C.-Y, Liu S.-T. Tetrahedron 2007; 63: 4304
- 21e Cai M, Zheng G, Ding G. Green Chem. 2009; 11: 1687
- 21f Cai M, Peng J, Hao W, Ding G. Green Chem. 2011; 13: 190
- 21g Hao W, Liu H, Yin L, Cai M. J. Org. Chem. 2016; 81: 4244
- 21h Havasi F, Ghorbani-Choghamarani A, Nikpour F. New J. Chem. 2015; 39: 6504
- 22 Shyu S.-G, Cheng S.-W, Tzou D.-L. Chem. Commun. 1999; 2337
- 23a Nunes CD, Valente AA, Pillinger M, Fernandes AC, Romao CC, Rocha J, Goncalves IS. J. Mater. Chem. 2002; 12: 1735
- 23b Jia M, Seifert A, Thiel WR. Chem. Mater. 2003; 15: 2174
- 24a Corma A, Gutierrez-Puebla E, Iglesias M, Monge A, Perez-Ferreras S, Sanchez F. Adv. Synth. Catal. 2006; 348: 1899
- 24b Corma A, Gonzalez-Arellano C, Iglesias M, Navarro MT, Sanchez F. Chem. Commun. 2008; 6218
- 24c Villaverde G, Corma A, Iglesias M, Sanchez F. ACS Catal. 2012; 2: 399
- 24d Yang W, Zhang R, Yi F, Cai M. J. Org. Chem. 2017; 82: 5204
- 25 Ibata T, Singh GS. Tetrahedron Lett. 1994; 35: 2581
- 26 Karthikeyan I, Alamsetti SK, Sekar G. Organometallics 2014; 33: 1665