Multi-gram scale mercury-free synthesis of optically pure 3,4,5-trisubstituted 1,2,4-triazoles using silver benzoate

Tetrahedron Letters

Volumn 51, Issue 19, 2010, Pages 2660-2663

  Bibian, Mathieu ^a   Blayo, Anne Laure ^a   Moulin, Aline ^a   Martinez, Jean ^a   Fehrentz, Jean Alain ^a  

^a UNIVERSITÉ DE MONTPELLIER   (France)

Author keywords

1,2,4 Triazole; Enantiopure; Heterocycles; Scale up; Silver

Indexed keywords

1,2,4 TRIAZOLE DERIVATIVE; BENZOIC ACID; MERCURY; SILVER; SILVER BENZOIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; CYCLIZATION; OPTICS; SCALE UP; SYNTHESIS;

EID: 77950363108     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.03.037     Document Type: Article

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23. General procedure for 1,2,4-triazole preparation: Thioamide (1 equiv) and hydrazide (1.2 equiv) were diluted in the minimum of dichloromethane. Silver benzoate (2 equiv) was then added immediately followed by acetic acid (3 equiv). The mixture was stirred overnight at room temperature. Distillation of the solvent under reduced pressure gave a black oil, which was diluted in a solution of dichloromethane. A flash chromatography on silica gel, eluted with AcOEt/hexane 5/5 to MeOH 5% in AcOEt, afforded the pure triazole in 40-90% yield.
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