Chemoselective synthesis of 4-[(Alkylsulfinyl)methyl]-3,5-dimethyl-1H-pyrazoles using hydrogen peroxide or 1,1-Di(hydroperoxy)cyclohexane

IF 1.7 3区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY

Journal of Sulfur Chemistry Pub Date : 2026-05-04 Epub Date: 2026-03-22 DOI:10.1080/17415993.2026.2642031

Larisa A. Baeva (Conceptualization Data curation Resources Writing – original draft) , Stanislav A. Grabovskii (Conceptualization Funding acquisition Visualization) , Rustam L. Safiullin (Data curation Funding acquisition Validation)

引用次数: 0

Abstract

A chemoselective method for synthesizing 4-[(alkylsulfinyl)methyl]-3,5-dimethyl-1H-pyrazoles via oxidation of the corresponding 4-[(alkylsulfanyl)methyl]-3,5-dimethyl-1H-pyrazoles is reported. The oxidation is performed under mild conditions using either hydrogen peroxide in acetone or 1,1-di(hydroperoxy)cyclohexane in benzene, achieving yields up to 98%. The methods are highly selective, halting at the sulfoxide stage even with excess oxidant. The influence of reaction conditions (oxidant concentration, solvent, and temperature) on the yield of sulfoxide is discussed, highlighting the efficiency and practicality of the proposed approach. The products were characterized by IR, ¹H NMR, ¹³C NMR, and mass spectrometry.

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过氧化氢或1,1-二（羟基过氧）环己烷化学选择性合成4-[（烷基亚砜基）甲基]-3,5-二甲基- 1h -吡唑

报道了一种通过氧化相应的4-[（烷基磺酰）甲基]-3,5-二甲基- 1h -吡唑合成4-[（烷基磺酰）甲基]-3,5-二甲基- 1h -吡唑的化学选择性方法。在温和的条件下，用丙酮中的过氧化氢或苯中的1,1-二（羟基）环己烷进行氧化，收率可达98%。该方法具有高度选择性，即使有过量的氧化剂，也能在亚砜阶段停止。讨论了反应条件（氧化剂浓度、溶剂和温度）对亚砜收率的影响，强调了该方法的效率和实用性。产物经IR、¹H NMR、¹³C NMR和质谱表征。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Journal of Sulfur Chemistry CHEMISTRY, MULTIDISCIPLINARY-

CiteScore

4.10

自引率

9.10%

发文量

审稿时长

6-12 weeks

期刊介绍： The Journal of Sulfur Chemistry is an international journal for the dissemination of scientific results in the rapidly expanding realm of sulfur chemistry. The journal publishes high quality reviews, full papers and communications in the following areas: organic and inorganic chemistry, industrial chemistry, materials and polymer chemistry, biological chemistry and interdisciplinary studies directly related to sulfur science. Papers outlining theoretical, physical, mechanistic or synthetic studies pertaining to sulfur chemistry are welcome. Hence the target audience is made up of academic and industrial chemists with peripheral or focused interests in sulfur chemistry. Manuscripts that truly define the aims of the journal include, but are not limited to, those that offer: a) innovative use of sulfur reagents; b) new synthetic approaches to sulfur-containing biomolecules, materials or organic and organometallic compounds; c) theoretical and physical studies that facilitate the understanding of sulfur structure, bonding or reactivity; d) catalytic, selective, synthetically useful or noteworthy transformations of sulfur containing molecules; e) industrial applications of sulfur chemistry; f) unique sulfur atom or molecule involvement in interfacial phenomena; g) descriptions of solid phase or combinatorial methods involving sulfur containing substrates. Submissions pertaining to related atoms such as selenium and tellurium are also welcome. Articles offering routine heterocycle formation through established reactions of sulfur containing substrates are outside the scope of the journal.