Synthesis 2016; 48(22): 3924-3930
DOI: 10.1055/s-0035-1562490
paper
© Georg Thieme Verlag Stuttgart · New York

Direct Access to 1,3,5-Trisubstituted 1H-1,2,4-Triazoles from N-Phenylbenzamidines via Copper-Catalyzed Diamination of Aryl Nitriles

Lutao Zhang
a   State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. of China
,
Dong Tang
a   State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. of China
,
Jing Gao
a   State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. of China
,
Jing Wang
a   State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. of China
,
Ping Wu
a   State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. of China
,
Xu Meng
b   State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, P. R. of China   eMail: chbh@lzu.edu.cn
,
Baohua Chen*
a   State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. of China
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Weitere Informationen

Publikationsverlauf

Received: 11. April 2016

Accepted after revision: 17. Mai 2016

Publikationsdatum:
28. Juni 2016 (online)


Abstract

A copper-catalyzed formation of C–N/N–N bonds using N-phenylbenzamidines with aryl nitriles has been developed and affords a route to 1,3,5-trisubstituted 1H-1,2,4-triazoles in moderate to excellent yields. The method is operationally simple and environmentally benign with a large substrate scope available and represents an economical path for numerous C–N/N–N bond formations.

Supporting Information

 
  • References

  • 1 Potts KT. Chem. Rev. 1961; 61: 87
    • 2a Xu H, Ma S, Xu Y, Bian L, Ding T, Fang X, Zhang W, Ren Y. J. Org. Chem. 2015; 80: 1789
    • 2b Liu X, Wang D, Chen B. Tetrahedron 2013; 69: 9417
    • 2c Lee J, Hong M, Jung Y, Cho EJ, Rhee H. Tetrahedron 2012; 68: 2045
    • 2d Al-Soud YA, Heydel M, Hartmann RW. Tetrahedron Lett. 2011; 52: 6372
    • 2e Su W, Yang D, Li J. Synth. Commun. 2005; 35: 1435
    • 3a Ito S, Tanaka Y, Kakehi A, Fukuyama T, Osawa N, Sayo N. Bull. Chem. Soc. Jpn. 1983; 56: 545
    • 3b Hoque AK. M. M, Kovelesky AC, Wang-Keun L, Shine HJ. Tetrahedron Lett. 1985; 26: 5655
    • 3c Staben ST, Blaquiere N. Angew. Chem. Int. Ed. 2010; 49: 325
    • 3d Guru MM, Punniyamurthy T. J. Org. Chem. 2012; 77: 5063
  • 4 Castanedo GM, Seng PS, Blaquiere N, Trapp S, Staben ST. J. Org. Chem. 2011; 76: 1177
  • 5 Huang H, Guo W, Wu W, Li CJ, Jiang H. Org. Lett. 2015; 17: 2894
  • 6 Ueda S, Nagasawa H. J. Am. Chem. Soc. 2009; 131: 15080
  • 7 Liao Q, Yang X, Xi C. J. Org. Chem. 2014; 79: 8507
  • 8 Li J, Neuville L. Org. Lett. 2013; 15: 1752
  • 9 Chen Z, Yan Q, Liu Z, Xu Y, Zhang Y. Angew. Chem. Int. Ed. 2013; 52: 13324
  • 10 Hirayama T, Ueda S, Okada T, Tsurue N, Okuda K, Nagasawa H. Chem. Eur. J. 2014; 20: 4156
    • 11a Zhang Y, Li X, Li J, Chen J, Meng X, Zhao M, Chen B. Org. Lett. 2012; 14: 26
    • 11b Wang D, Li N, Zhao M, Shi W, Ma C, Chen B. Green Chem. 2010; 12: 2120
  • 12 Liu X, Wang D, Chen Y, Tang D, Chen B. Adv. Synth. Catal. 2013; 355: 2798
  • 13 Qu J, Wu P, Tang D, Meng X, Chen Y, Guo S, Chen B. New J. Chem. 2015; 39: 4235
    • 14a Allen SE, Walvoord RR, Padilla-Salinas R, Kozlowski MC. Chem. Rev. 2013; 113: 6234
    • 14b Song L, Tian X, Lv Z, Li E, Wu J, Liu Y, Yu W, Chang J. J. Org. Chem. 2015; 80: 7219
    • 14c Zheng Z, Ma S, Tang L, Zhang-Negrerie D, Du Y, Zhao K. J. Org. Chem. 2014; 79: 4687
    • 14d Sun M, Chen C, Bao W. RSC Adv. 2014; 4: 47373
    • 14e Wang L.-Y, Tsai HJ, Lin H.-Y, Kaneko K, Cheng F.-Y, Shih H.-S, Wong FF, Huang J.-J. RSC Adv. 2014; 4: 14215
    • 14f Tam A, Armstrong IS, La Cruz TE. Org. Lett. 2013; 15: 3586
    • 14g Wang Y, Wang H, Peng J, Zhu Q. Org. Lett. 2011; 13: 4604
  • 15 Meng X, Yu C, Zhao P. RSC Adv. 2014; 4: 8612
    • 16a Mal K, Das S, Maiti NC, Natarajan R, Das I. J. Org. Chem. 2015; 80: 2972
    • 16b Mishra S, Monir K, Mitra S, Hajra A. Org. Lett. 2014; 16: 6084
    • 16c Aschwanden P, Frantz DE, Carreira EM. Org. Lett. 2000; 2: 2331
  • 17 Perez M, Dorado C, Soto J. Synthesis 1983; 6: 483
  • 18 Wang F, You Q, Wu C, Min D, Shi T, Kong Y, Zhang W. RSC Adv. 2015; 5: 78422