Larisa A. Baeva, Rail R. Gataullin, Radik M. Nugumanov
{"title":"通过 3-[(烷基硫)甲基]戊烷-2,4-二酮与苯胺的反应合成三乙酰基取代的 1,2,3,4-四氢吡啶","authors":"Larisa A. Baeva, Rail R. Gataullin, Radik M. Nugumanov","doi":"10.1007/s10593-024-03301-7","DOIUrl":null,"url":null,"abstract":"<p>The condensation of 3-[(alkylsulfanyl)methyl]pentane-2,4-diones with aniline in the presence of catalytic amounts of acetic acid led to the formation of 1,1',1''-(6-methyl-1-phenyl-1,2,3,4-tetrahydropyridine-3,3,5-triyl)triethanone. The reaction is presumably a tandem process, incorporating the formation of β-enaminone, elimination of the alkanethiol molecule from the β-enaminone and the starting pentane-2,4-dione, and a subsequent [4+2] cycloaddition of the resulting intermediates. The mechanism of the conversion may also involve intramolecular cyclization of the Michael addition products of 3-[(alkylsulfanyl)methyl]pentane-2,4-dione to 3-(imidoyl)but-3-en-2-one, formed from β-enaminones during the elimination of alkanethiols.</p>","PeriodicalId":9770,"journal":{"name":"Chemistry of Heterocyclic Compounds","volume":null,"pages":null},"PeriodicalIF":1.4000,"publicationDate":"2024-04-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"A synthesis of triacetyl-substituted 1,2,3,4-tetrahydropyridine by the reaction of 3-[(alkylsulfanyl)methyl]pentane-2,4-diones with aniline\",\"authors\":\"Larisa A. Baeva, Rail R. Gataullin, Radik M. Nugumanov\",\"doi\":\"10.1007/s10593-024-03301-7\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p>The condensation of 3-[(alkylsulfanyl)methyl]pentane-2,4-diones with aniline in the presence of catalytic amounts of acetic acid led to the formation of 1,1',1''-(6-methyl-1-phenyl-1,2,3,4-tetrahydropyridine-3,3,5-triyl)triethanone. The reaction is presumably a tandem process, incorporating the formation of β-enaminone, elimination of the alkanethiol molecule from the β-enaminone and the starting pentane-2,4-dione, and a subsequent [4+2] cycloaddition of the resulting intermediates. The mechanism of the conversion may also involve intramolecular cyclization of the Michael addition products of 3-[(alkylsulfanyl)methyl]pentane-2,4-dione to 3-(imidoyl)but-3-en-2-one, formed from β-enaminones during the elimination of alkanethiols.</p>\",\"PeriodicalId\":9770,\"journal\":{\"name\":\"Chemistry of Heterocyclic Compounds\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":1.4000,\"publicationDate\":\"2024-04-08\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Chemistry of Heterocyclic Compounds\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1007/s10593-024-03301-7\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Chemistry of Heterocyclic Compounds","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1007/s10593-024-03301-7","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
A synthesis of triacetyl-substituted 1,2,3,4-tetrahydropyridine by the reaction of 3-[(alkylsulfanyl)methyl]pentane-2,4-diones with aniline
The condensation of 3-[(alkylsulfanyl)methyl]pentane-2,4-diones with aniline in the presence of catalytic amounts of acetic acid led to the formation of 1,1',1''-(6-methyl-1-phenyl-1,2,3,4-tetrahydropyridine-3,3,5-triyl)triethanone. The reaction is presumably a tandem process, incorporating the formation of β-enaminone, elimination of the alkanethiol molecule from the β-enaminone and the starting pentane-2,4-dione, and a subsequent [4+2] cycloaddition of the resulting intermediates. The mechanism of the conversion may also involve intramolecular cyclization of the Michael addition products of 3-[(alkylsulfanyl)methyl]pentane-2,4-dione to 3-(imidoyl)but-3-en-2-one, formed from β-enaminones during the elimination of alkanethiols.
期刊介绍：
The international journal Chemistry of Heterocyclic Compounds publishes original papers, short communications, reviews, and mini-reviews dealing with problems in the field of heterocyclic chemistry in Russian and English. The Journal also publishes reviews and annotations on new books and brief reports on conferences in the field of heterocyclic chemistry, as well as commemoratives dedicated to prominent heterocyclic chemists.
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