{"title":"通过硝基烯的非催化异狄尔斯-阿尔德反应合成 1,2-恶嗪 N-氧化物(微型综述)","authors":"Radomir Jasiński","doi":"10.1007/s10593-024-03304-4","DOIUrl":null,"url":null,"abstract":"\n<figure></figure><p>In this microreview, the application of noncatalyzed hetero-Diels–Alder reaction (formally [4+2] cycloaddition) with participation of conjugated nitroalkenes and their analogs for easy and selective preparation of 1,2-oxazine <i>N</i>-oxides was reviewed on the basis of recent publications. It was found that the best described processes are realized with full regioselectivity as well as at mild temperatures. It is interesting, that in some cases of the title reactions, the stepwise mechanism of the formation of the six-membered heterocyclic ring is more possible than classic one-step mechanism.</p><figure><picture><source srcset=\"//media.springernature.com/lw685/springer-static/image/art%3A10.1007%2Fs10593-024-03304-4/MediaObjects/10593_2024_3304_Figd_HTML.png?as=webp\" type=\"image/webp\"/><img alt=\"\" height=\"2\" loading=\"lazy\" src=\"//media.springernature.com/lw685/springer-static/image/art%3A10.1007%2Fs10593-024-03304-4/MediaObjects/10593_2024_3304_Figd_HTML.png\" width=\"685\"/></picture></figure>","PeriodicalId":9770,"journal":{"name":"Chemistry of Heterocyclic Compounds","volume":null,"pages":null},"PeriodicalIF":1.4000,"publicationDate":"2024-06-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Synthesis of 1,2-oxazine N-oxides via noncatalyzed hetero-Diels–Alder reactions of nitroalkenes (microreview)\",\"authors\":\"Radomir Jasiński\",\"doi\":\"10.1007/s10593-024-03304-4\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"\\n<figure></figure><p>In this microreview, the application of noncatalyzed hetero-Diels–Alder reaction (formally [4+2] cycloaddition) with participation of conjugated nitroalkenes and their analogs for easy and selective preparation of 1,2-oxazine <i>N</i>-oxides was reviewed on the basis of recent publications. It was found that the best described processes are realized with full regioselectivity as well as at mild temperatures. It is interesting, that in some cases of the title reactions, the stepwise mechanism of the formation of the six-membered heterocyclic ring is more possible than classic one-step mechanism.</p><figure><picture><source srcset=\\\"//media.springernature.com/lw685/springer-static/image/art%3A10.1007%2Fs10593-024-03304-4/MediaObjects/10593_2024_3304_Figd_HTML.png?as=webp\\\" type=\\\"image/webp\\\"/><img alt=\\\"\\\" height=\\\"2\\\" loading=\\\"lazy\\\" src=\\\"//media.springernature.com/lw685/springer-static/image/art%3A10.1007%2Fs10593-024-03304-4/MediaObjects/10593_2024_3304_Figd_HTML.png\\\" width=\\\"685\\\"/></picture></figure>\",\"PeriodicalId\":9770,\"journal\":{\"name\":\"Chemistry of Heterocyclic Compounds\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":1.4000,\"publicationDate\":\"2024-06-03\",\"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/s10593-024-03304-4\",\"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/s10593-024-03304-4","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Synthesis of 1,2-oxazine N-oxides via noncatalyzed hetero-Diels–Alder reactions of nitroalkenes (microreview)
In this microreview, the application of noncatalyzed hetero-Diels–Alder reaction (formally [4+2] cycloaddition) with participation of conjugated nitroalkenes and their analogs for easy and selective preparation of 1,2-oxazine N-oxides was reviewed on the basis of recent publications. It was found that the best described processes are realized with full regioselectivity as well as at mild temperatures. It is interesting, that in some cases of the title reactions, the stepwise mechanism of the formation of the six-membered heterocyclic ring is more possible than classic one-step mechanism.
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.