{"title":"Recent Advances in Denitrogenative Organic Transformations of 1,2,3‐Benzotriazin‐4(3H)‐ones","authors":"","doi":"10.1002/ajoc.202400127","DOIUrl":null,"url":null,"abstract":"<div><p>Denitrogenative organic transformations and related reactions are a class of significant approaches for carrying out unusual C−C/C‐heteroatom (C−O, C−N, C−S) bond‐forming reactions that are usually promoted by Ru, Ir, Pd, Ni, and Cu metal catalysts. In this trait, numerous methods were adopted to synthesize several pharmaceutically valuable <em>N</em>‐ and <em>O</em>‐containing heteroaromatics using 1,2,3‐benzotriazin‐4(3<em>H</em>)‐one as an electrophilic coupling partner. This review involves the recent achievements related to the metal/organo‐catalyzed thermal and visible‐light mediated denitrogenative approaches with 1,2,3‐benzotriazin‐4(3<em>H</em>)‐ones towards the synthesis of imperative <em>N</em>‐heteroaromatic compounds. In addition, metal and oxidant‐free <em>ortho</em>‐functionalization of benzotriazinones by using suitable nucleophilic partners have been discussed. In particular, the most novel methods employing Ni and Pd metal catalysts that have emerged are exhibited. Specific attention has been paid to offering the detailed mechanistic pathway to explain the role of metal catalysts and the mechanism in the absence of metal catalysts in the denitrogenative reactions under a thermal/visible light medium.</p></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 7","pages":"Article e202400127"},"PeriodicalIF":2.8000,"publicationDate":"2024-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Asian Journal of Organic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S2193580724001120","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
Denitrogenative organic transformations and related reactions are a class of significant approaches for carrying out unusual C−C/C‐heteroatom (C−O, C−N, C−S) bond‐forming reactions that are usually promoted by Ru, Ir, Pd, Ni, and Cu metal catalysts. In this trait, numerous methods were adopted to synthesize several pharmaceutically valuable N‐ and O‐containing heteroaromatics using 1,2,3‐benzotriazin‐4(3H)‐one as an electrophilic coupling partner. This review involves the recent achievements related to the metal/organo‐catalyzed thermal and visible‐light mediated denitrogenative approaches with 1,2,3‐benzotriazin‐4(3H)‐ones towards the synthesis of imperative N‐heteroaromatic compounds. In addition, metal and oxidant‐free ortho‐functionalization of benzotriazinones by using suitable nucleophilic partners have been discussed. In particular, the most novel methods employing Ni and Pd metal catalysts that have emerged are exhibited. Specific attention has been paid to offering the detailed mechanistic pathway to explain the role of metal catalysts and the mechanism in the absence of metal catalysts in the denitrogenative reactions under a thermal/visible light medium.
变氮有机转化及相关反应是进行不寻常的 C-C/C-杂原子(C-O、C-N、C-S)成键反应的一类重要方法,通常由 Ru、Ir、Pd、Ni 和 Cu 金属催化剂促进。在这一特性中,采用了多种方法,以 1,2,3-苯并三嗪-4(3H)-酮为亲电偶联剂,合成了多种具有药用价值的含 N 和 O 的杂芳香族化合物。本综述介绍了最近在 1,2,3-苯并三嗪-4(3H)-酮的金属/有机物催化热和可见光介导的脱氮方法方面取得的成就,这些方法用于合成必需的 N-杂芳香族化合物。此外,还讨论了利用合适的亲核伙伴对苯并三嗪酮进行无金属和无氧化剂的正官能化。特别是展示了采用镍和钯金属催化剂的最新颖方法。还特别注意提供详细的机理途径,以解释金属催化剂的作用,以及在热/可见光介质下没有金属催化剂的脱氮反应机理。
期刊介绍:
Organic chemistry is the fundamental science that stands at the heart of chemistry, biology, and materials science. Research in these areas is vigorous and truly international, with three major regions making almost equal contributions: America, Europe and Asia. Asia now has its own top international organic chemistry journal—the Asian Journal of Organic Chemistry (AsianJOC)
The AsianJOC is designed to be a top-ranked international research journal and publishes primary research as well as critical secondary information from authors across the world. The journal covers organic chemistry in its entirety. Authors and readers come from academia, the chemical industry, and government laboratories.