{"title":"Mn(III)-Based Oxidation of (Methylene)Bis(Cyclodiamide)s. Facile Synthesis of Tetraazadispiro-(Undecanone)s and -(Tridecanone)s","authors":"Haruki Kamachi, Takumi Toki, Ayaka Nakamura, Hiroshi Nishino","doi":"10.1002/jhet.4891","DOIUrl":null,"url":null,"abstract":"<div>\n \n <p>The oxidation of 5,5′-(methylene)bis(6-hydroxy-1,3-dimethylpyrimidine-2,4(1<i>H</i>,3<i>H</i>)-dione) monopiperidinium salts with Mn(OAc)<sub>3</sub>•2H<sub>2</sub>O was carried out in boiling MeCN, producing 2,4,9,11-tetramethyl-2,4,9,11-tetraazadispiro[5.0.5<sup>7</sup>.1<sup>6</sup>]tridecane-1,3,5,8,10,12-hexaones in high yields. A similar reaction using 4,4′-(methylene)bis(1,2-diphenylpyrazolidine-3,5-dione)s gave 2,3,8,9-tetraphenyl-2,3,8,9-tetraazadispiro[4.0.4<sup>6</sup>.1<sup>5</sup>]undecane-1,4,7,10-tetraones in good yields. The structure determination and the reaction mechanism for the formation of the unique tetraazadispiro(cyclopropane)s are discussed.</p>\n </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 11","pages":"1729-1739"},"PeriodicalIF":2.0000,"publicationDate":"2024-09-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Heterocyclic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://onlinelibrary.wiley.com/doi/10.1002/jhet.4891","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
The oxidation of 5,5′-(methylene)bis(6-hydroxy-1,3-dimethylpyrimidine-2,4(1H,3H)-dione) monopiperidinium salts with Mn(OAc)3•2H2O was carried out in boiling MeCN, producing 2,4,9,11-tetramethyl-2,4,9,11-tetraazadispiro[5.0.57.16]tridecane-1,3,5,8,10,12-hexaones in high yields. A similar reaction using 4,4′-(methylene)bis(1,2-diphenylpyrazolidine-3,5-dione)s gave 2,3,8,9-tetraphenyl-2,3,8,9-tetraazadispiro[4.0.46.15]undecane-1,4,7,10-tetraones in good yields. The structure determination and the reaction mechanism for the formation of the unique tetraazadispiro(cyclopropane)s are discussed.
期刊介绍：
The Journal of Heterocyclic Chemistry is interested in publishing research on all aspects of heterocyclic chemistry, especially development and application of efficient synthetic methodologies and strategies for the synthesis of various heterocyclic compounds. In addition, Journal of Heterocyclic Chemistry promotes research in other areas that contribute to heterocyclic synthesis/application, such as synthesis design, reaction techniques, flow chemistry and continuous processing, multiphase catalysis, green chemistry, catalyst immobilization and recycling.
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