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Volumn , Issue 2, 2007, Pages 278-282

A convenient synthesis of 1,4,5-trisubstituted 1,2,3-triazoles via 1,3-dipolar cycloaddition/coupling of alkynes, phenylboronic acids, and sodium azide catalyzed by Cu(I)/Cu(II)

Author keywords

Alkyne; Copper catalyst; Cycloaddition coupling; Phenylboronic acid; Triazole

Indexed keywords

1,2,3 TRIAZOLE DERIVATIVE; ALKYNE DERIVATIVE; BENZENEBORONIC ACID; CUPRIC ION; CUPROUS ION; DIOXANE DERIVATIVE; SODIUM AZIDE; TRIAZOLE DERIVATIVE; WATER;

EID: 33847366341     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-968007     Document Type: Article
Times cited : (53)

References (31)
  • 8
    • 84943402961 scopus 로고
    • Katritzky, A. R, Rees, C. W, Eds, Pergamon: Oxford
    • Wamhoff, H. In Comprehensive Heterocyclic Chemistry, Vol. 5; Katritzky, A. R.; Rees, C. W., Eds.; Pergamon: Oxford, 1984, 669.
    • (1984) Comprehensive Heterocyclic Chemistry , vol.5 , pp. 669
    • Wamhoff, H.1
  • 28
    • 33847396672 scopus 로고    scopus 로고
    • Synthesis of 4-(4-Methoxyphenyl)-5-[2-(4-methoxyphenyl)ethynyl]-1- phenyl-1H-1,2,3-triazole (4a, Typical Procedure: A mixture of 1a (50.0 mg, 0.41 mmol, 2a (118.9 mg, 0.90 mmol, sodium azide (3; 40.3 mg, 0.62 mmol, CuI (7.8 mg, 0.041 mmol) and CuSO 4·5H2O (20.5 mg, 0.082 mmol) in 1,4-dioxane (10 mL) and H2O (5 mL) was stirred overnight. Then, the reaction mixture was diluted with H2O (20 mL) and was extracted with CH 2Cl2 (3 x 20 mL, The combined organic extracts were dried over MgSO4, filtered and concentrated. The residue was purified by column chromatography (PE-EtOAc, 10:1) to afford 4a (98.5 mg, 63, as a white solid; mp 86-88°C. IR (KBr, 2216 cm-1. 1H NMR (300 MHz, CDCl3, δ, 3.83 (s, 3 H, 3.87 (s, 3 H, 6.89 (d, J, 9.3 Hz, 2 H, 7.03 (d, J, 8.7 Hz, 2 H, 7.40 d, J, 8.7 Hz
    • 3): δ = 2.67 (s, 3 H), 3.84 (s, 3 H), 3.87 (s, 3 H), 6.91
  • 31
    • 33847422428 scopus 로고    scopus 로고
    • -1, F(000) = 672.0. Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication CCDC-626008.
    • -1, F(000) = 672.0. Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication CCDC-626008.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.