{"title":"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","authors":"Z Najminejad, D Azarifar, S-M Khatami","doi":"10.1007/s12039-024-02341-y","DOIUrl":null,"url":null,"abstract":"<div><p>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.</p><h3>Graphical abstract</h3><p>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\n</p><div><figure><div><div><picture><source><img></source></picture></div></div></figure></div></div>","PeriodicalId":616,"journal":{"name":"Journal of Chemical Sciences","volume":"137 1","pages":""},"PeriodicalIF":1.7000,"publicationDate":"2025-02-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Monoacetylated bishydroperoxide-derived singlet molecular oxygen-mediated oxidative coupling of primary and secondary alcohols with phenylhydrazine: Synthesis of 1,3,5-trisubstituted pyrazoles\",\"authors\":\"Z Najminejad, D Azarifar, S-M Khatami\",\"doi\":\"10.1007/s12039-024-02341-y\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>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.</p><h3>Graphical abstract</h3><p>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\\n</p><div><figure><div><div><picture><source><img></source></picture></div></div></figure></div></div>\",\"PeriodicalId\":616,\"journal\":{\"name\":\"Journal of Chemical Sciences\",\"volume\":\"137 1\",\"pages\":\"\"},\"PeriodicalIF\":1.7000,\"publicationDate\":\"2025-02-27\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Journal of Chemical Sciences\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://link.springer.com/article/10.1007/s12039-024-02341-y\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Chemical Sciences","FirstCategoryId":"92","ListUrlMain":"https://link.springer.com/article/10.1007/s12039-024-02341-y","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
Monoacetylated bishydroperoxide-derived singlet molecular oxygen-mediated oxidative coupling of primary and secondary alcohols with phenylhydrazine: Synthesis of 1,3,5-trisubstituted pyrazoles
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
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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