26069-99-8Relevant academic research and scientific papers
Sulfite-Induced N-Alkylation and Thioketonization of Azoles Enable Access to Diverse Azole Thiones
Deng, Jian-Chao,Chen, Jia-Hao,Zhang, Jun-Rong,Lu, Ting-Ting,Tang, Ri-Yuan
, p. 4795 - 4806 (2018)
The direct modification of azole skeletons enables access to drug-like molecules. The development of a highly compatible reaction platform for this pursuit still remains challenging. Herein, we report the use of sulfite as the single electron transfer (SET) reducing agent for the activation of functionalized bromoalkanes, elemental sulfur, and imidazoliniums for the transition metal-free and base-free N-alkylation and thioketonization of azoles. Excellent functional group tolerance and high synthetic efficiency proved particularly advantageous for the rapid assembly of a large array of pharmaceutically-oriented azole thiones, many of which contain synthetically and biologically useful functional groups. The direct transformation of drug molecules (such as Ketoconazole, Econazole, and Fluconazole) into their corresponding azole thiones has also been successfully achieved. Reactions with selenium also proceeded smoothly under the optimized conditions. Successful gram-scale reactions demonstrate the good applicability of this methodology. (Figure presented.).
Azole thioketone(selenium ketone) derivative and preparation method and application thereof
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Paragraph 0051-0055, (2019/01/08)
The invention belongs to the technical field of preparation of an azole thioketone(selenium ketone) derivative, and concretely relates to an azole thioketone(selenium ketone) derivative and a preparation method and an application thereof. The preparation method comprises the following concrete steps: weighing one of an azole compound, elemental sulfur or selenium as well as a catalyst sulfite, andadding an organic solvent to a reaction vessel, injecting halogenated alkane and reacting the material under heating condition to obtain a corresponding thioketone or selenium ketone derivative whichis the azole thioketone(selenium ketone) derivative. The method for preparing an azole thioketone(selenium ketone) derivative has the advantages of simple process, mild conditions, low cost and economy, and high efficiency; the azole thioketone(selenium ketone) derivative has excellent bactericidal and bacteriostatic activity, and has inhibitory activity against penicillium italicum, gibberella saubinetii, gloeosporium musarum, and colletotrichum gloeosporioides.
