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Synthesis and Crystallographic Characterization of 1-((2-(2,4-Difluorophenyl)oxiran-2-yl)methyl)-1H-1,2,4-triazole: A Crucial Intermediate for the Synthesis of Azole Antifungal Drugs

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Abstract

Preparation of oxirane 3 was accomplished in two steps. 1H-1,2,4-triazole was reacted with 2,4-difluoro-α-chloroacetophenone 1 in presence of K2CO3 in refluxing toluene to provide compound 2. Compound 2 was treated with trimethylsulfoxonium iodide (TMSI) in aq. NaOH and toluene to provide oxirane 3. Oxirane 3, previously isolated as an oil, was crystallized from (DCM/MeOH) and characterized by X-ray crystallography: triclinic, space group P − 1, a = 7.3225 (15), b = 7.5833 (15), c = 9.856 (2) Å, α = 91.908 (12), β = 100.824 (11), γ = 103.800 (11)°, V = 520.28 (18) Å3, Z = 2. The molecule has a stepped conformation with nearly parallel triazole and phenyl rings. Lack of classical hydrogen-bond donors leads to packing dominated by weaker interactions, including C–H···N, C–H···F and F···F contacts.

Graphical Abstract

This important intermediate, normally an oil, has been crystallized, and its crystal structure includes a stepped conformation with nearly parallel triazole and phenyl rings. Lack of classical hydrogen-bond donors leads to packing dominated by weaker interactions, including C–H···N, C–H···F and F···F contacts.

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Acknowledgments

Support to TT in the form of start-up funds and resources from the College of Pharmacy and Allied Health Professions of St. John’s University are gratefully acknowledged. The purchase of the diffractometer was made possible by grant No. LEQSF (1999–2000)-ENH-TR-13, administered by the Louisiana Board of Regents.

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Authors and Affiliations

  1. Department of Pharmaceutical Sciences, College of Pharmacy and Allied Health Professions, St. John’s University, Jamaica, NY, 11439, USA

    Pallav D. Patel & Tanaji T. Talele

  2. Department of Chemistry, Louisiana State University, Baton Rouge, LA, 70803, USA

    Frank R. Fronczek

Authors
  1. Pallav D. Patel
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  2. Tanaji T. Talele
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  3. Frank R. Fronczek
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Correspondence to Tanaji T. Talele or Frank R. Fronczek.

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Patel, P.D., Talele, T.T. & Fronczek, F.R. Synthesis and Crystallographic Characterization of 1-((2-(2,4-Difluorophenyl)oxiran-2-yl)methyl)-1H-1,2,4-triazole: A Crucial Intermediate for the Synthesis of Azole Antifungal Drugs. J Chem Crystallogr 39, 923–926 (2009). https://doi.org/10.1007/s10870-009-9593-1

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