Ana Da Lama, José Pérez Sestelo, Luis A. Sarandeses, M. Montserrat Martínez
{"title":"铟(III)催化的同丙炔基叠氮化物分子内环化合成吡咯和苯并[g]吲哚的过程","authors":"Ana Da Lama, José Pérez Sestelo, Luis A. Sarandeses, M. Montserrat Martínez","doi":"10.1021/acs.joc.4c01768","DOIUrl":null,"url":null,"abstract":"Pyrroles, privileged structural motifs in drug and material science, have been synthesized by indium(III)-catalyzed intramolecular cyclization of homopropargyl azides. This methodology exhibits a broad substrate scope, providing substituted pyrroles and bispyrroles in good yields. Furthermore, an atom-economical sequential method for the synthesis of benzo[<i>g</i>]indoles has been discovered from azido-diynes using InCl<sub>3</sub> as catalyst. The method involves two successive intramolecular indium-catalyzed 5<i>-endo-dig</i> alkyne hydroamination and a hydroarylation reactions with 6<i>-endo-dig</i> regioselectivity.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3000,"publicationDate":"2024-10-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Indium(III)-Catalyzed Synthesis of Pyrroles and Benzo[g]indoles by Intramolecular Cyclization of Homopropargyl Azides\",\"authors\":\"Ana Da Lama, José Pérez Sestelo, Luis A. Sarandeses, M. Montserrat Martínez\",\"doi\":\"10.1021/acs.joc.4c01768\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"Pyrroles, privileged structural motifs in drug and material science, have been synthesized by indium(III)-catalyzed intramolecular cyclization of homopropargyl azides. This methodology exhibits a broad substrate scope, providing substituted pyrroles and bispyrroles in good yields. Furthermore, an atom-economical sequential method for the synthesis of benzo[<i>g</i>]indoles has been discovered from azido-diynes using InCl<sub>3</sub> as catalyst. The method involves two successive intramolecular indium-catalyzed 5<i>-endo-dig</i> alkyne hydroamination and a hydroarylation reactions with 6<i>-endo-dig</i> regioselectivity.\",\"PeriodicalId\":57,\"journal\":{\"name\":\"The Journal of Organic Chemistry\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":3.3000,\"publicationDate\":\"2024-10-15\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"The Journal of Organic Chemistry\",\"FirstCategoryId\":\"1\",\"ListUrlMain\":\"https://doi.org/10.1021/acs.joc.4c01768\",\"RegionNum\":2,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"The Journal of Organic Chemistry","FirstCategoryId":"1","ListUrlMain":"https://doi.org/10.1021/acs.joc.4c01768","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Indium(III)-Catalyzed Synthesis of Pyrroles and Benzo[g]indoles by Intramolecular Cyclization of Homopropargyl Azides
Pyrroles, privileged structural motifs in drug and material science, have been synthesized by indium(III)-catalyzed intramolecular cyclization of homopropargyl azides. This methodology exhibits a broad substrate scope, providing substituted pyrroles and bispyrroles in good yields. Furthermore, an atom-economical sequential method for the synthesis of benzo[g]indoles has been discovered from azido-diynes using InCl3 as catalyst. The method involves two successive intramolecular indium-catalyzed 5-endo-dig alkyne hydroamination and a hydroarylation reactions with 6-endo-dig regioselectivity.
期刊介绍:
The Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.