Synthesis 2019; 51(21): 3998-4005
DOI: 10.1055/s-0039-1690159
paper
© Georg Thieme Verlag Stuttgart · New York

[3+2]-Cycloaddition of α-Diazocarbonyl Compounds with Arenediazonium Salts Catalyzed by Silver Nitrate Delivers 2,5-Disubstituted Tetrazoles

Sergey Chuprun
,
Dmitry Dar’in
,
Grigory Kantin
,
This research was supported by the Russian Science Foundation (project grant 19-75-30008).
Further Information

Publication History

Received: 25 June 2019

Accepted after revision: 22 July 2019

Publication Date:
12 August 2019 (eFirst)

Abstract

[3+2]-Cycloaddition of arenediazonium salts with diazo compounds (earlier exemplified only for trimethylsilyldiazomethane and 2,2,2-trifluorodiazoethane) has been developed to include a wide range of readily available α-diazocarbonyl compounds. The resulting 2-aryl-5-acyl-2H-tetrazoles are of high value in medicinal chemistry.

Supporting Information

 
  • References

  • 1 Address correspondence to this author at the Laboratory of Chemical Pharmacology, Institute of Chemistry, Saint Petersburg State University, 26 Universitetskyi prospekt, Peterhof 198504, Russian Federation.
  • 2 Current address: Department of Chemistry and Biochemistry, Florida International University, 11200 SW 8th St., Miami, FL 33199, USA.
  • 3 Ostrovskii VA, Trifonov RE, Popova EA. Russ. Chem. Bull. 2012; 61: 768
  • 4 Herr RJ. Bioorg. Med. Chem. 2002; 10: 3379
  • 5 Scaffold Hopping in Medicinal Chemistry . Brown N. Wiley-VCH; Weinheim: 2014
    • 6a Yates P, Farnum DG. Tetrahedron Lett. 1960; 48 (38) : 22
    • 6b Wittenberger SJ. Org. Prep. Proced. Int. 1994; 26: 499
    • 6c Roh J, Vavrova K, Hrabalek A. Eur. J. Org. Chem. 2012; 6101
    • 6d Ito S, Tanaka Y, Kakehi A. Bull. Chem. Soc. Jpn. 1976; 49: 762
    • 6e Bernstein PR, Vacek EP. Synthesis 1987; 1133
    • 6f Alterman M, Hallberg A. J. Org. Chem. 2000; 65: 7984
    • 6g Demko ZP, Sharpless KB. J. Org. Chem. 2001; 66: 7945
    • 6h Jin T, Kamijo S, Yamamoto Y. Tetrahedron Lett. 2004; 45: 9435
    • 6i Gutmann B, Roduit J.-P, Roberge D, Kappe CO. Angew. Chem. Int. Ed. 2010; 49: 7101
    • 6j Li Y, Gao L.-X, Han FS. Chem. Commun. 2012; 48: 2719
    • 6k Onaka T, Umemoto H, Miki Y, Nakamura A, Maegawa T. J. Org. Chem. 2014; 79: 6703
  • 7 Chen Z, Fan S.-Q, Zheng Y, Ma J.-A. Chem. Commun. 2015; 51: 16545
  • 8 Patouret R, Kamenecka TM. Tetrahedron Lett. 2016; 57: 1597
    • 9a Isaac M, Slassi A, Edwards L, Dove P, Xin T, Stefanac T. PCT Int. Appl WO 2008041075, 2008 ; Chem. Abstr. 2008, 148, 449638
    • 9b Arzel E, Edwards L, Isaac M, Mcleod DA, Slassi A, Xin T. PCT Int. Appl WO 2009051556, 2009 ; Chem. Abstr. 2009, 150, 447953.
  • 10 Garfunkle J, Ezzili C, Rayl TJ, Hochstatter DG, Hwang I, Boger DL. J. Med. Chem. 2008; 51: 4392
  • 11 Hsieh H.-P, Hsu T.-A, Yeh J.-Y, Chao Y.-S. US Pat. Appl 20110263620, 2011 ; Chem. Abstr. 2011, 155, 606928
  • 12 Yamanoi S, Namiki H, Ochiai Y, Hoshino M, Matsumoto K. PCT Int. Appl WO 2013108800, 2013 ; Chem. Abstr. 2013, 159, 260144
  • 13 Filimonov VD, Trusova M, Postnikov P, Krasnokutskaya EA, Lee YM, Hwang HY, Kim H, Chi K.-W. Org. Lett. 2008; 10: 3961
  • 14 Kutonova KV, Trusova ME, Stankevich AV, Postnikov PS, Filimonov VD. Beilstein J. Org. Chem. 2015; 11: 358
  • 15 Wang S, Yang L.-J, Zeng J.-L, Zheng Y, Ma J.-A. Org. Chem. Front. 2015; 2: 1468
  • 16 Wilds AL, Meader AL. J. Org. Chem. 1948; 13: 763
  • 17 Zhang J, Chen W, Huang D, Zeng X, Wang X, Hu Y. J. Org. Chem. 2017; 82: 9171
  • 18 Shu W.-M, Ma J.-R, Zheng K.-L, Sun H.-Y, Wang M, Yang Y, Wu A.-X. Tetrahedron 2014; 70: 9321
  • 19 Kim KS, Kimball SD, Misra RN, Rawlins DB, Hunt JT, Xiao H.-Y, Lu S, Qian L, Han W.-C, Shan W, Mitt T, Cai Z.-W, Poss MA, Zhu H, Sack JS, Tokarski JS, Chang CY, Pavletich N, Kamath A, Humphreys WG, Marathe P, Bursuker I, Kellar KA, Roongta U, Batorsky R, Mulheron JG, Bol D, Fairchild CR, Lee FY, Webster KR. J. Med. Chem. 2002; 45: 3905
  • 20 Musio B, Mariani F, Sliwinski EP, Kabeshov MA, Odajima H, Ley SV. Synthesis 2016; 48: 3515
  • 21 Sezer O, Dabak K, Anac O, Akar A. Helv. Chim. Acta 1997; 80: 960
  • 22 Zhang L, Sun B, Liu Q, Mo F. J. Org. Chem. 2018; 83: 4275
  • 23 Doeben N, Yan H, Kischkewitz M, Mao J, Studer A. Org. Lett. 2018; 20: 7933