{"title":"PIFA 介导的苯酚系 1,2-二唑分子内脱芳作用：螺环己二烯酮吡唑并[3,4-b]哌啶酮的合成","authors":"Pradeep Natarajan, Pratibha Bachhley, Sweta Tripathy, Ashok Vasantharaj P, S. Peruncheralathan","doi":"10.1055/a-2382-9631","DOIUrl":null,"url":null,"abstract":"In recent years, the significance of spirocyclic motifs in drug discovery has increased, owing to their unique ability to engage biological targets. We present the first example of PIFA-mediated dearomative spirocyclization of phenol-tethered pyrazoles, highlighting intramolecular trapping by the pyrazole moiety. This method efficiently affords a variety of spirocyclohexadienone pyrazolo[3,4-b]piperidinones with yields of up to 82%. Mechanistic studies reveal that the dearomatization process involves a cationic intermediate.","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":null,"pages":null},"PeriodicalIF":0.0000,"publicationDate":"2024-08-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"PIFA-Mediated Intramolecular Dearomatization of Phenol-Tethered 1,2-Diazoles: Synthesis of Spirocyclohexadienone Pyrazolo[3,4-b]piperidinones\",\"authors\":\"Pradeep Natarajan, Pratibha Bachhley, Sweta Tripathy, Ashok Vasantharaj P, S. Peruncheralathan\",\"doi\":\"10.1055/a-2382-9631\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"In recent years, the significance of spirocyclic motifs in drug discovery has increased, owing to their unique ability to engage biological targets. We present the first example of PIFA-mediated dearomative spirocyclization of phenol-tethered pyrazoles, highlighting intramolecular trapping by the pyrazole moiety. This method efficiently affords a variety of spirocyclohexadienone pyrazolo[3,4-b]piperidinones with yields of up to 82%. Mechanistic studies reveal that the dearomatization process involves a cationic intermediate.\",\"PeriodicalId\":501298,\"journal\":{\"name\":\"Synthesis\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2024-08-08\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Synthesis\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://doi.org/10.1055/a-2382-9631\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"\",\"JCRName\":\"\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Synthesis","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.1055/a-2382-9631","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
PIFA-Mediated Intramolecular Dearomatization of Phenol-Tethered 1,2-Diazoles: Synthesis of Spirocyclohexadienone Pyrazolo[3,4-b]piperidinones
In recent years, the significance of spirocyclic motifs in drug discovery has increased, owing to their unique ability to engage biological targets. We present the first example of PIFA-mediated dearomative spirocyclization of phenol-tethered pyrazoles, highlighting intramolecular trapping by the pyrazole moiety. This method efficiently affords a variety of spirocyclohexadienone pyrazolo[3,4-b]piperidinones with yields of up to 82%. Mechanistic studies reveal that the dearomatization process involves a cationic intermediate.
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