Synthesis of 1,4-Disubstituted 1H-1,2,3-Triazoles from 4-(1-Adamantyl)benzyl Azide through a 1,3-Dipolar Cycloaddition Reaction

Abstract

A series of new 1,4-disubstituted 1H-1,2,3-triazole derivatives were synthesized by an efficient copper-catalyzed 1,3-dipolar cyclo­addition reaction of 4-(1-adamantyl)benzyl azide with several terminal alkynes. The copper catalyst was used to provide 1,4-disubstituted 1,2,3-triazoles regioselectively in good yields.

Key words

triazoles - 1,3-dipolar cycloaddition - copper catalysis - one-pot process - adamantylbenzyl azide - click chemistry

• References and Notes

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• 33 {1-[4-(1-Adamantyl)benzyl]-1H-1,2,3-triazol-4-yl}methanol (5b) White solid; yield: 314 mg (81%); mp 168 °C. IR (run as NaCl discs): 3200, 1025, 2900, 2847 cm⁻¹. ¹H NMR: δ = 7.46 (s, 1 H, triazole-H), 7.39 (d, J = 8.4 Hz, 2 H, Ar-H), 7.26 (d, J = 8.3 Hz, 2 H, Ar-H), 5.48 (s, 2 H, CH₂–N), 4.75 (s, 2 H, CH₂–O), 2.80 (s, 1 H, OH), 2.09–2.17 (m, 3 H, ad-H), 1.92 (br d, 6 H, ad-H), 1.81–1.80 (m, 6 H, ad-H). ¹³C NMR: δ = 152.3 (Ar-Cq), 143.9 (triazole-Cq), 131.5 (1 C, Ar-Cq), 128.1, 125.8 (4 C, Ar-C), 121.7 (1 C, Ar-C), 120.2 (triazole-CH), 56.6 (CH₂–O), 54.1 (s, CH₂–N), 43.2 (3 C, CH₂, ad-C), 36.8 (3 C, CH₂, ad-C), 36.3 (ad-Cq), 28.9 (3 C, CH, ad-C). HRMS (ESI⁺): m/z [M + H]⁺ calcd for C₂₀H₂₆N₃O: 324.2077; found: 324.2068.
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