Microwave irradiation as an effective means of synthesizing uninfstituted N-linked 1,2,3-triazoles from vinyl acetate and azides

Synlett

Volumn , Issue 20, 2009, Pages 3275-3278

  Hansen, Signe Grann ^a   Jensen, Henrik Helligsø ^a  

^a AARHUS UNIVERSITY   (Denmark)

Author keywords

1,2,3 triazole; 1,3 dipolar cycloaddition; Microwave irradiation; One pot reaction; Vinyl acetate

Indexed keywords

1,2,3 TRIAZOLE DERIVATIVE; AZIDE; ETHER; HALIDE; TETRABUTYLAMMONIUM; VINYL ACETATE;

ARTICLE; CYCLOADDITION; MICROWAVE IRRADIATION; ONE POT SYNTHESIS; REACTION TIME; SUBSTITUTION REACTION; SYNTHESIS;

EID: 72249102810     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1218366     Document Type: Article

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30. Microwave-Assisted One-Pot Formation of 1,2,3- Triazole from Alkyl Halides; General Procedure WARNING: Excess azide can potentially react with acetic acid to form explosive hydrazoic acid. Thus, vinyl acetate should not be added before the azidation reaction has run to completion, and proper safety precautions should be taken when handling these compounds. Alkyl halide (1 equiv) and tetrabutylammonium azide (1.05 equiv) were dissolved in diethyl ether (1 mL) in a sealed Biotage vial and irradiated at 100 °C until TLC analysis indicated full consumption of the starting material. Vinyl acetate (10 equiv) was then added and the reaction mixture was irradiated at 120 °C until TLC analysis showed disappearance of the intermediate azide. The reaction mixture was then diluted with diethyl ether and the organic phase was washed with H2O and brine then dried over MgSO4, concentrated under reduced pressure and purified by column chromatography on silica gel. 1-Benzyl-1H-1,2,3-triazole: BnCl (50 mL, 0.35 mmol) and TBAN (104 mg, 0.36 mmol) in Et2O (1.0 mL) was irradiated at 100 °C for 15 min. Vinyl acetate (0.32 mL, 3.5 mmol) was added and the reaction mixture was irradiated at 120 °C for 9 h. Flash column chromatography (EtOAc-CH2Cl2, 1:9; Rf = 0.41) afforded the triazole as colorless crystals (36 mg, 64%).