{"title":"利用苄基插入的结果实现π-扩展吡啶-吖啶和喹唑啉-菲啶。","authors":"","doi":"10.1039/d4ob00533c","DOIUrl":null,"url":null,"abstract":"<div><p>Distinct protocols have been devised for the preparation of hybrid heterocyclic scaffolds like π-extended pyrido-acridines and quinazolino-phenanthridines duly materialized through Rh(<span>iii</span>)- and Pd(<span>ii</span>)-mediated catalytic courses commencing from acridine and quinazolimine scaffolds. Interestingly, the parent compounds (acridines and quinazolimines) are actualized from 2-aminobenzonitrile and anthranilic acid, where 2-aminobenzonitrile acts as the 1,4-dipolarophilic species and anthranilic acid as the benzyne precursor. The molecular assembly of acridine suggests the participation of two benzyne units. In addition, the structural motif of the quinazolimine ring features one benzyne unit. Further, indolizine ring containing the enaminonitrile skeleton upon exposure to benzyne forms an indolizine fused quinoline ring, decorated with three benzyne units.</p></div>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9000,"publicationDate":"2024-07-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Harnessing the benzyne insertion consequence to enable π-extended pyrido-acridine and quinazolino-phenanthridine†‡\",\"authors\":\"\",\"doi\":\"10.1039/d4ob00533c\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>Distinct protocols have been devised for the preparation of hybrid heterocyclic scaffolds like π-extended pyrido-acridines and quinazolino-phenanthridines duly materialized through Rh(<span>iii</span>)- and Pd(<span>ii</span>)-mediated catalytic courses commencing from acridine and quinazolimine scaffolds. Interestingly, the parent compounds (acridines and quinazolimines) are actualized from 2-aminobenzonitrile and anthranilic acid, where 2-aminobenzonitrile acts as the 1,4-dipolarophilic species and anthranilic acid as the benzyne precursor. The molecular assembly of acridine suggests the participation of two benzyne units. In addition, the structural motif of the quinazolimine ring features one benzyne unit. Further, indolizine ring containing the enaminonitrile skeleton upon exposure to benzyne forms an indolizine fused quinoline ring, decorated with three benzyne units.</p></div>\",\"PeriodicalId\":96,\"journal\":{\"name\":\"Organic & Biomolecular Chemistry\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":2.9000,\"publicationDate\":\"2024-07-10\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic & Biomolecular Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/org/science/article/pii/S1477052024005676\",\"RegionNum\":3,\"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":"Organic & Biomolecular Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S1477052024005676","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Harnessing the benzyne insertion consequence to enable π-extended pyrido-acridine and quinazolino-phenanthridine†‡
Distinct protocols have been devised for the preparation of hybrid heterocyclic scaffolds like π-extended pyrido-acridines and quinazolino-phenanthridines duly materialized through Rh(iii)- and Pd(ii)-mediated catalytic courses commencing from acridine and quinazolimine scaffolds. Interestingly, the parent compounds (acridines and quinazolimines) are actualized from 2-aminobenzonitrile and anthranilic acid, where 2-aminobenzonitrile acts as the 1,4-dipolarophilic species and anthranilic acid as the benzyne precursor. The molecular assembly of acridine suggests the participation of two benzyne units. In addition, the structural motif of the quinazolimine ring features one benzyne unit. Further, indolizine ring containing the enaminonitrile skeleton upon exposure to benzyne forms an indolizine fused quinoline ring, decorated with three benzyne units.