I2/TBPB Mediated Oxidative Reaction of N-Tosylhydrazones with Anilines: Practical Construction of 1,4-Disubstituted 1,2,3-Triazoles under Metal-Free and Azide-Free Conditions

cFan, W.Q.; Katritzky, A. R.InComprehensive Heterocyclic Chemistry II;Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V., Eds.Elsevier Science:Oxford, 1996; Vol.4, pp1–126.

[4]

Alvarez R. J. Med. Chem. (1994) 10.1021/jm00050a015

[5]

Baures P. W. Org. Lett. (1999) 10.1021/ol990586y

[6]

fPalmer, L. M.; Janson, C. A.; Smith, W. W.PCT Int. Appl. 2005; p347. CODEN: PIXXD2 WO 2005016237 A2 20050224, CAN: 142:256748 (patent written in English).

[7]

Huisgen R. Angew. Chem., Int. Ed. Engl. (1963) 10.1002/anie.196305651

[8]

Huisgen R. Angew. Chem., Int. Ed. Engl. (1963) 10.1002/anie.196306331

[9]

Huisgen R. Chem. Ber. (1965) 10.1002/cber.19650981228

[10]

Rostovtsev V. V. Angew. Chem., Int. Ed. (2002) 10.1002/1521-3773(20020715)41:14<2596::aid-anie2596>3.0.co;2-4

[11]

Peptidotriazoles on Solid Phase: [1,2,3]-Triazoles by Regiospecific Copper(I)-Catalyzed 1,3-Dipolar Cycloadditions of Terminal Alkynes to Azides

Christian W. Tornøe, Caspar Christensen, Morten Meldal

The Journal of Organic Chemistry 2002 10.1021/jo011148j

[12]

Click Chemistry: Diverse Chemical Function from a Few Good Reactions

Hartmuth C. Kolb, M. G. Finn, K. Barry Sharpless

Angewandte Chemie International Edition 2001 10.1002/1521-3773(20010601)40:11<2004::aid-anie2004>3.0.co;2-5

[13]

Moses J. E. Chem. Soc. Rev. (2007) 10.1039/b613014n

[14]

Meldal M. Chem. Rev. (2008)

[15]

Thirumurugan P. Chem. Rev. (2013) 10.1021/cr200409f

[16]

Paterson M. J. J. Am. Chem. Soc. (2004) 10.1021/ja0386593

[17]

Lober S. Org. Lett. (2004) 10.1021/ol049598w

[18]

Efficiency and Fidelity in a Click‐Chemistry Route to Triazole Dendrimers by the Copper(I)‐Catalyzed Ligation of Azides and Alkynes

Peng Wu, Alina K. Feldman, Anne K. Nugent et al.

Angewandte Chemie International Edition 2004 10.1002/anie.200454078

[19]

Brik A. ChemBioChem (2003) 10.1002/cbic.200300724

[20]

Lee L. V. J. Am. Chem. Soc. (2003) 10.1021/ja0302836

[21]

Wu Y. M. Synthesis (2005) 10.1055/s-2005-861860

[22]

Nolte C. Angew. Chem., Int. Ed. (2007) 10.1002/anie.200604444

[23]

Kuijpers B. H. M. Synlett (2005)

[24]

Gerard B. Tetrahedron (2006) 10.1016/j.tet.2006.04.025

[25]

Zhang X. Chem. Commun. (2007) 10.1039/b701040k

[26]

Hein J. E. Angew. Chem., Int. Ed. (2009) 10.1002/anie.200903558

[27]

Zhang L. J. Am. Chem. Soc. (2005) 10.1021/ja054114s

[28]

Ding S. Angew. Chem., Int. Ed. (2014) 10.1002/anie.201309855

[29]

Barluenga J. Angew. Chem., Int. Ed. (2006) 10.1002/anie.200601045

[30]

Ramachary D. B. Chem.—Eur. J. (2008) 10.1002/chem.200801325

[31]

Danence L. J. T. Chem.—Eur. J. (2011) 10.1002/chem.201002775

[32]

Belkheira M. Chem.—Eur. J. (2011) 10.1002/chem.201102046

[33]

Thomas J. Angew. Chem., Int. Ed. (2014) 10.1002/anie.201403453

[34]

Sakai K. Bull. Chem. Soc. Jpn. (1986) 10.1246/bcsj.59.179

[35]

van Berkel S. S. Angew. Chem., Int. Ed. (2012) 10.1002/anie.201108850

[36]

Chen Z. Angew. Chem., Int. Ed. (2013) 10.1002/anie.201306416

[37]

Cai Z.-J. Org. Lett. (2013) 10.1021/ol4023936

[38]

Hao W.-J. J. Org. Chem. (2013) 10.1021/jo401773j

[39]

Compounds3gand3vwere determined by X-ray crystallography. See theSupporting Informationfor full details. CCDC 1001829 (3g) and 1001828 (3v) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre viawww.ccdc.cam.ac.uk/data_request/cif.

[40]

Attanasi O. A. Eur. J. Org. Chem. (2009) 10.1002/ejoc.200900243

[41]

Rossi E. Angew. Chem., Int. Ed. (2002) 10.1002/1521-3773(20020415)41:8<1400::aid-anie1400>3.0.co;2-3

[42]

Attanasi O. A. Org. Lett. (2008) 10.1021/ol800557h

[43]

Attanasi O. A. Org. Lett. (2010) 10.1021/ol902642z

[44]

Attanasi O. A. Adv. Synth. Catal. (2011) 10.1002/adsc.201100094

[45]

Chen J.-R. J. Am. Chem. Soc. (2012) 10.1021/ja301196x

[46]

Hatcher J. M. J. Am. Chem. Soc. (2010) 10.1021/ja100932q

[47]

Tong M.-C. Angew. Chem., Int. Ed. (2014) 10.1002/anie.201400109

[48]

Grirrane A. Science (2008) 10.1126/science.1166401

[49]

Grirrane A. Nat. Protoc. (2010) 10.1038/nprot.2009.242

[50]

Takeda Y. Angew. Chem., Int. Ed. (2012) 10.1002/anie.201202786

Showing 50 of 53 references

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Details

Published: Sep 24, 2014
Vol/Issue: 16(19)
Pages: 5108-5111

Authors

Z

Zhong-Jian Cai