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DOI: 10.1055/s-0029-1217175
One-Pot, Three-Component Copper-Catalysed ‘Click’ Triazole Synthesis Utilising the Inexpensive, Shelf-Stable Diazotransfer Reagent Imidazole-1-sulfonyl Azide Hydrochloride
Publikationsverlauf
Publikationsdatum:
13. Mai 2009 (online)
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Abstract
A practical and efficient one-pot procedure for the regioselective synthesis of functionalised 1,4-disubstituted 1,2,3-triazoles from primary amines and terminal acetylenes has been established utilising the inexpensive, shelf-stable diazotransfer reagent imidazole-1-sulfonyl azide hydrochloride.
Key words
cycloaddition - triazole - combinatorial chemistry - diazotransfer reagent - one-pot reaction
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References and Notes
Typical Reaction
Procedure
To a solution of 1H-imidazole-1-sulfonyl
azide˙HCl (210 mg, 1 mmol) in MeOH (6 mL) was added benzylamine (0.109
mL, 1.00 mmol), phenylacetylene (0.110 mL, 1.00 mmol), copper(II)
sulfate pentahydrate (25 mg, 0.1 mmol), sodium ascorbate (40 mg,
0.2 mmol), and Et3N (0.139 mL, 1.00 mmol) under nitrogen.
The resulting suspension was stirred or shaken at r.t. for 20 h.
The mixture was concen-trated onto SiO2 and purified
by flash chromatography (SiO2), elution gradient 10-90% Et2O
in isohexane. Pure fractions were evaporated to give 1-benzyl-4-phenyl-1H-1,2,3-triazole (211 mg, 90%)
as a white solid. HRMS: m/z calcd:
236.1188 [M + H]+;
found: 236.1178 [M + H]+. ¹H NMR
(500.3 MHz, CDCl3): δ = 7.81 (m, 2
H), 7.66 (s, 1 H), 7.35 (m, 8 H), 5.58 (s, 2 H). ¹³C
NMR (125.8 MHz, CDCl3): δ = 148.26,
134.69, 130.53, 129.19, 128.89, 128.20, 128.09, 125.72, 119.51,
54.27. Mp 120.8-122 ˚C;¹4 120-122 ˚C.