Monoacetylated bishydroperoxide-derived singlet molecular oxygen-mediated oxidative coupling of primary and secondary alcohols with phenylhydrazine: Synthesis of 1,3,5-trisubstituted pyrazoles

IF 2 4区 化学 Q3 CHEMISTRY, MULTIDISCIPLINARY Journal of Chemical Sciences Pub Date : 2025-02-27 DOI:10.1007/s12039-024-02341-y
Z Najminejad, D Azarifar, S-M Khatami
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Abstract

Oxidative synthesis of pyrazoles from aromatic alcohols and phenyl hydrazine has been achieved by using trans-5-hydroperoxy-3,5-dimethyl-1,2-dioxolan-3-yl ethaneperoxate and KOH. The reaction proceeds via oxidative coupling of primary and secondary alcohols with phenylhydrazines by singlet molecular oxygen produced from trans-5-hydroperoxy-3,5-dimethyl-1,2-dioxolane-3-yl ethaneperoxate at room temperature, and broad range of derivatives were obtained in good to excellent yields. Advantageous features of the present methodology include mild reaction conditions, transition metal-free, good functional-group tolerance, use of readily available primary and secondary alcohols and so on.

Graphical abstract

Oxidative synthesis of pyrazoles from aromatic alcohols and phenyl hydrazine has been achieved by using trans-5-hydroperoxy-3,5-dimethyl-1,2-dioxolan-3-yl ethaneperoxate/KOH. The reaction proceeds via oxidative coupling of primary and secondary alcohols with phenylhydrazines by singlet oxygen produced from trans-5-hydroperoxy-3,5-dimethyl-1,2-dioxolane-3-yl ethaneperoxate and a range of derivatives were obtained in good to excellent yields

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单乙酰化双过氧化氢衍生单线态分子氧介导的伯、仲醇与苯肼的氧化偶联:1,3,5-三取代吡唑的合成
以反式5-羟基过氧基3,5-二甲基-1,2-二恶唑-3-酰基乙过氧酸盐和KOH为原料,实现了芳香醇和苯基肼氧化合成吡唑的工艺。在室温下,由反式5-羟基-3,5-二甲基-1,2-二恶唑烷-3-酰基过氧乙酯生成单线态分子氧,使伯、仲醇与苯肼发生氧化偶联反应,得到了多种收率较高的衍生物。本方法的优点包括反应条件温和,无过渡金属,官能团耐受性好,使用易得的伯醇和仲醇等。以反式5-羟基过氧基3,5-二甲基-1,2-二恶唑-3-烷基乙过氧盐/KOH为原料,实现了芳香醇和苯基肼的氧化合成吡唑。由反式5-羟基过氧-3,5-二甲基-1,2-二恶烷-3-酰基过氧酯生成的单线态氧将伯、仲醇与苯基肼氧化偶联,得到了一系列收率较高的衍生物
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来源期刊
Journal of Chemical Sciences
Journal of Chemical Sciences CHEMISTRY, MULTIDISCIPLINARY-
CiteScore
3.10
自引率
5.90%
发文量
107
审稿时长
1 months
期刊介绍: Journal of Chemical Sciences is a monthly journal published by the Indian Academy of Sciences. It formed part of the original Proceedings of the Indian Academy of Sciences – Part A, started by the Nobel Laureate Prof C V Raman in 1934, that was split in 1978 into three separate journals. It was renamed as Journal of Chemical Sciences in 2004. The journal publishes original research articles and rapid communications, covering all areas of chemical sciences. A significant feature of the journal is its special issues, brought out from time to time, devoted to conference symposia/proceedings in frontier areas of the subject, held not only in India but also in other countries.
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