Regioselective synthesis of 1,4-disubstituted 1,2,3-triazoles via three-component coupling of secondary alcohols, TMSN3 and alkynes

Tetrahedron Letters

Volumn 48, Issue 33, 2007, Pages 5831-5834

  Sreedhar, B ^a   Reddy, P Surendra ^a   Krishna, V Rama ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

1,3 Dipolar cycloaddition; 1,4 Disubstituted 1,2,3 triazoles; Azide; Cu(OTf)2; Secondary alcohols

Indexed keywords

1,2,3 TRIAZOLE DERIVATIVE; ALCOHOL; ALKYNE; AZIDE; COPPER; SOLVENT; TRIMETHYLSILYL AZIDE; UNCLASSIFIED DRUG;

ALLERGY; ANTIBACTERIAL ACTIVITY; ANTICONVULSANT ACTIVITY; ANTIVIRAL ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; CYCLOADDITION; DRUG STRUCTURE; MASS SPECTROMETRY; ONE POT SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 34447521579     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.06.069     Document Type: Article

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22. 2 (3 mol %) in nitromethane (3 mL) was stirred at 60 °C for 3 h and the extent of reaction was monitored by TLC. Phenylacetylene (1.1 mmol) and Cu-powder (3 mol %) were added and the reaction was stirred at 60 °C for 3 h. After completion of the reaction (as monitored by TLC), the catalyst was filtered through Celite and the product was extracted with ethyl acetate (3 × 10 mL). After drying and removal of the solvent under vacuum, the crude product was purified by column chromatography on silica gel (hexane-ethyl acetate (12:88)) to afford pure product. All products gave satisfactory spectroscopic and analytical data.
23. 3: C, 78.96; H, 7.89; N, 13.15. Found: C, 78.92; H, 7.92; N, 13.15. See Supplementary data for spectral data of all other compounds.