Febee R. Louka , Lily G. Ortte , Madison R. Maier , Nahed M.H. Salem , Ana Torvisco , Roland C. Fischer , Franz A. Mautner , Salah S. Massoud
{"title":"以哌嗪为基础合成 1,3-噁嗪类化合物","authors":"Febee R. Louka , Lily G. Ortte , Madison R. Maier , Nahed M.H. Salem , Ana Torvisco , Roland C. Fischer , Franz A. Mautner , Salah S. Massoud","doi":"10.1016/j.molstruc.2024.140693","DOIUrl":null,"url":null,"abstract":"<div><div>The oxazines bearing piperazinyl moieties namely 2-(<em>tert-</em>butyl)-6-((4-(2-(8-(<em>tert</em>-butyl)-6-methyl-<em>2H</em>-benzo[<em>e</em>][1,3]oxazin-3(<em>4H</em>)-yl)ethyl)piperazin-1-yl)methyl)-4-methylphenol (1) and its corresponding 2,4-di-<em>tert</em>-butyl-6-((4-(2-(6,8-di-<em>tert</em>-butyl-<em>2H</em>-benzo[<em>e</em>]-[1,3]oxazin-3(<em>4H</em>)-yl)ethyl)piperazin-1-yl)methyl)phenol (2), which was previously isolated were described. The transformation of the piperazinyl tri-<em>tert</em>-butyl-phenol derivatives 6,6′-(((2-(4-(3-(<em>tert</em>-butyl)-2-hydroxy-5-methylbenzyl)piperazin-1-yl)ethyl)-azanediyl)bis-(methylene))bis-(2-(<em>tert-</em>butyl)-4-methylphenol) 3 and 6,6′-(((2-(4-(3,5-di-<em>tert</em>-butyl-2-hydroxybenzyl)piperazin-1-yl)ethyl)-azanediyl)-bis(methylene))bis(2,4-di-<em>tert</em>-butyl-phenol) 4 into 1 and 2, respectively was achieved in high yield by heating and stirring a methanolic solution containing Et<sub>3</sub>N and Ga(NO<sub>3</sub>)<sub>3</sub>·6H<sub>2</sub>O in the stochiometric ratio 1:3:1 for 30 min. The novel oxazine-piperazine 1 together with its triphenol-piperazine 3 (H<sub>3</sub>L<sup>4</sup>) were structurally characterized by spectroscopic and single crystal X-ray crystallography.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1323 ","pages":"Article 140693"},"PeriodicalIF":4.0000,"publicationDate":"2024-11-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Synthesis of 1,3-oxazines based on piperazine\",\"authors\":\"Febee R. Louka , Lily G. Ortte , Madison R. Maier , Nahed M.H. Salem , Ana Torvisco , Roland C. Fischer , Franz A. Mautner , Salah S. Massoud\",\"doi\":\"10.1016/j.molstruc.2024.140693\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>The oxazines bearing piperazinyl moieties namely 2-(<em>tert-</em>butyl)-6-((4-(2-(8-(<em>tert</em>-butyl)-6-methyl-<em>2H</em>-benzo[<em>e</em>][1,3]oxazin-3(<em>4H</em>)-yl)ethyl)piperazin-1-yl)methyl)-4-methylphenol (1) and its corresponding 2,4-di-<em>tert</em>-butyl-6-((4-(2-(6,8-di-<em>tert</em>-butyl-<em>2H</em>-benzo[<em>e</em>]-[1,3]oxazin-3(<em>4H</em>)-yl)ethyl)piperazin-1-yl)methyl)phenol (2), which was previously isolated were described. The transformation of the piperazinyl tri-<em>tert</em>-butyl-phenol derivatives 6,6′-(((2-(4-(3-(<em>tert</em>-butyl)-2-hydroxy-5-methylbenzyl)piperazin-1-yl)ethyl)-azanediyl)bis-(methylene))bis-(2-(<em>tert-</em>butyl)-4-methylphenol) 3 and 6,6′-(((2-(4-(3,5-di-<em>tert</em>-butyl-2-hydroxybenzyl)piperazin-1-yl)ethyl)-azanediyl)-bis(methylene))bis(2,4-di-<em>tert</em>-butyl-phenol) 4 into 1 and 2, respectively was achieved in high yield by heating and stirring a methanolic solution containing Et<sub>3</sub>N and Ga(NO<sub>3</sub>)<sub>3</sub>·6H<sub>2</sub>O in the stochiometric ratio 1:3:1 for 30 min. The novel oxazine-piperazine 1 together with its triphenol-piperazine 3 (H<sub>3</sub>L<sup>4</sup>) were structurally characterized by spectroscopic and single crystal X-ray crystallography.</div></div>\",\"PeriodicalId\":16414,\"journal\":{\"name\":\"Journal of Molecular Structure\",\"volume\":\"1323 \",\"pages\":\"Article 140693\"},\"PeriodicalIF\":4.0000,\"publicationDate\":\"2024-11-12\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Journal of Molecular Structure\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0022286024032010\",\"RegionNum\":2,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, PHYSICAL\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Molecular Structure","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0022286024032010","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, PHYSICAL","Score":null,"Total":0}
The oxazines bearing piperazinyl moieties namely 2-(tert-butyl)-6-((4-(2-(8-(tert-butyl)-6-methyl-2H-benzo[e][1,3]oxazin-3(4H)-yl)ethyl)piperazin-1-yl)methyl)-4-methylphenol (1) and its corresponding 2,4-di-tert-butyl-6-((4-(2-(6,8-di-tert-butyl-2H-benzo[e]-[1,3]oxazin-3(4H)-yl)ethyl)piperazin-1-yl)methyl)phenol (2), which was previously isolated were described. The transformation of the piperazinyl tri-tert-butyl-phenol derivatives 6,6′-(((2-(4-(3-(tert-butyl)-2-hydroxy-5-methylbenzyl)piperazin-1-yl)ethyl)-azanediyl)bis-(methylene))bis-(2-(tert-butyl)-4-methylphenol) 3 and 6,6′-(((2-(4-(3,5-di-tert-butyl-2-hydroxybenzyl)piperazin-1-yl)ethyl)-azanediyl)-bis(methylene))bis(2,4-di-tert-butyl-phenol) 4 into 1 and 2, respectively was achieved in high yield by heating and stirring a methanolic solution containing Et3N and Ga(NO3)3·6H2O in the stochiometric ratio 1:3:1 for 30 min. The novel oxazine-piperazine 1 together with its triphenol-piperazine 3 (H3L4) were structurally characterized by spectroscopic and single crystal X-ray crystallography.
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