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Synlett 2021; 32(01): 86-90
DOI: 10.1055/s-0040-1707321
letter

Potassium tert-Butoxide Promoted Synthesis of 4,5-Diaryl-2H-1,2,3-triazoles from Tosylhydrazones and Nitriles

Shanguang Qiu
,
Yuxue Chen
,
Xinming Song
,
Li Liu
,
Xi Liu
,
Luyong Wu∗
Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, Hainan Normal University, No. 99, Longkun South Road, Haikou 571158, P. R. of China   Email: wuluyong@hainnu.edu.cn
› Author AffiliationsThis work was supported by the Natural Science Foundation of Hainan Province (219MS044) and the National Natural Science Foundation of China (NSFC-21562019).
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Abstract

Intermolecular cycloaddition of tosylhydrazones with nitriles was investigated. t-BuOK was shown to be an excellent base for increasing the effectiveness of the reaction in this protocol, and homocoupling of the tosylhydrazones was significantly inhibited by using xylene as a solvent. Through this transformation, a variety of 4,5-diaryl-2H-1,2,3-triazoles were prepared in good to excellent yields and with high purities. The process is azide-free and transition-metal-free.

Key words

triazoles - tosylhydrazones - cycloaddition - potassium butoxide

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1707321.
  • Supporting Information


Publication History

Received: 24 July 2020

Accepted after revision: 14 September 2020

Article published online:
12 October 2020

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  • 20 4,5-Diaryl-2H-1,2,3-triazoles 3a–t, 4a–ag; General Procedure A mixture of the appropriate tosylhydrazone 1 (1.0 mmol), nitrile 2 (1.2 mmol), and t-BuOK (3.0 mmol) in xylene (6 mL) was stirred at 90 °C for 4 h under Ar. The mixture was then cooled to r.t. and diluted with EtOAc (40 mL). The organic layer was washed with water (3 × 40 mL) and brine (30 mL), then dried (Na2SO4) and filtered. The filtrate was concentrated in vacuum, and the crude product was purified by column chromatography (silica gel, PE–EtOAc). 4,5-Bis(4-methoxyphenyl)-2H-1,2,3-triazole (4x) White solid; yield: 261.3 mg (93%); mp 121.9–124.9 °C. 1H NMR (400 MHz, CDCl3): δ = 7.41 (d, J = 8.8 Hz, 4 H), 6.79 (d, J = 8.9 Hz, 4 H), 3.74 (s, 6 H). 13C NMR (100 MHz, CDCl3): δ = 159.5, 140.6, 129.3, 122.2, 113.9, 55.0.