将硝基环氧化物环化为吡啶鎓 1,4-齐聚硫酸酯以合成吲哚利嗪衍生物的[(5 + 1) - 1

IF 4.4 2区化学 Q2 CHEMISTRY, APPLIED

Advanced Synthesis & Catalysis Pub Date : 2024-10-17 DOI:10.1002/adsc.202400961

Al-Hajaj Hamood Al-Maani, Ahmad Takallou, Yazdanbakhsh Lotfi Nosood, Sulaiman Al-Shidhani, Mohammad Reza Hosseini, Muhammad Usman Anwar, Ahmed Al-Harrasi

{"title":"将硝基环氧化物环化为吡啶鎓 1,4-齐聚硫酸酯以合成吲哚利嗪衍生物的[(5 + 1) - 1","authors":"Al-Hajaj Hamood Al-Maani, Ahmad Takallou, Yazdanbakhsh Lotfi Nosood, Sulaiman Al-Shidhani, Mohammad Reza Hosseini, Muhammad Usman Anwar, Ahmed Al-Harrasi","doi":"10.1002/adsc.202400961","DOIUrl":null,"url":null,"abstract":"The synthesis of indolizine derivatives was achieved through the reaction of pyridinium 1,4-zwitterionic thiolates with a diverse array of 2-methyl-2-nitro-3-aryloxiranes. Subsequent investigations unveiled a synthetic route to indolizines via a stepwise [(5 + 1) - 1] pathway, with unstable pyridothiazines serving as transient intermediates. DFT calculations elucidated that this transformation entails sequential annulation, deacylation, desulfurization, and oxidation steps.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"11 1","pages":""},"PeriodicalIF":4.4000,"publicationDate":"2024-10-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"[(5 + 1) - 1] Cyclization of Nitroepoxides to Pyridinium 1,4-Zwitterionic Thiolates for the Synthesis of Indolizine Derivatives\",\"authors\":\"Al-Hajaj Hamood Al-Maani, Ahmad Takallou, Yazdanbakhsh Lotfi Nosood, Sulaiman Al-Shidhani, Mohammad Reza Hosseini, Muhammad Usman Anwar, Ahmed Al-Harrasi\",\"doi\":\"10.1002/adsc.202400961\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"The synthesis of indolizine derivatives was achieved through the reaction of pyridinium 1,4-zwitterionic thiolates with a diverse array of 2-methyl-2-nitro-3-aryloxiranes. Subsequent investigations unveiled a synthetic route to indolizines via a stepwise [(5 + 1) - 1] pathway, with unstable pyridothiazines serving as transient intermediates. DFT calculations elucidated that this transformation entails sequential annulation, deacylation, desulfurization, and oxidation steps.\",\"PeriodicalId\":118,\"journal\":{\"name\":\"Advanced Synthesis & Catalysis\",\"volume\":\"11 1\",\"pages\":\"\"},\"PeriodicalIF\":4.4000,\"publicationDate\":\"2024-10-17\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Advanced Synthesis & Catalysis\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1002/adsc.202400961\",\"RegionNum\":2,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, APPLIED\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Advanced Synthesis & Catalysis","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1002/adsc.202400961","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, APPLIED","Score":null,"Total":0}

引用次数: 0

摘要

吲哚利嗪衍生物的合成是通过吡啶鎓 1,4- 齐聚物硫醇与多种 2-甲基-2-硝基-3-芳环氧乙烷的反应实现的。随后的研究揭示了一条通过逐步[(5 + 1) - 1]途径合成吲嗪类化合物的路线，其中不稳定的吡啶噻嗪类化合物是瞬时中间体。DFT 计算阐明，这一转化过程包括连续的环化、脱酰基、脱硫和氧化步骤。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

查看原文本刊更多论文

[(5 + 1) - 1] Cyclization of Nitroepoxides to Pyridinium 1,4-Zwitterionic Thiolates for the Synthesis of Indolizine Derivatives

The synthesis of indolizine derivatives was achieved through the reaction of pyridinium 1,4-zwitterionic thiolates with a diverse array of 2-methyl-2-nitro-3-aryloxiranes. Subsequent investigations unveiled a synthetic route to indolizines via a stepwise [(5 + 1) - 1] pathway, with unstable pyridothiazines serving as transient intermediates. DFT calculations elucidated that this transformation entails sequential annulation, deacylation, desulfurization, and oxidation steps.

求助全文

通过发布文献求助，成功后即可免费获取论文全文。去求助

来源期刊

Advanced Synthesis & Catalysis 化学-应用化学

CiteScore

9.40

自引率

7.40%

发文量

447

审稿时长

1.8 months

期刊介绍： Advanced Synthesis & Catalysis (ASC) is the leading primary journal in organic, organometallic, and applied chemistry. The high impact of ASC can be attributed to the unique focus of the journal, which publishes exciting new results from academic and industrial labs on efficient, practical, and environmentally friendly organic synthesis. While homogeneous, heterogeneous, organic, and enzyme catalysis are key technologies to achieve green synthesis, significant contributions to the same goal by synthesis design, reaction techniques, flow chemistry, and continuous processing, multiphase catalysis, green solvents, catalyst immobilization, and recycling, separation science, and process development are also featured in ASC. The Aims and Scope can be found in the Notice to Authors or on the first page of the table of contents in every issue.