{"title":"Substrate- and reagent-dependent selective annulation of amidines and 2-tert-amino benzaldehydes†","authors":"Yi Zhang , Renchao Ma , Yongmin Ma , Weiwei Fang","doi":"10.1039/d5ob00424a","DOIUrl":null,"url":null,"abstract":"<div><div>Herein, we present an efficient and substrate/reagent-dependent annulation of amidines with 2-<em>tert</em>-amino benzaldehydes. When <em>N</em>-alkyl benzimidamides are employed, amidines undergo self-annulation to generate a hydrotriazine skeleton. In contrast, <em>N</em>-aryl benzimidamides yield quinazolines/hydroquinazolines under similar conditions. Additionally, the coupling of 2-<em>tert</em>-amino benzaldehydes with amidines under basic conditions yields 1,3,5-triazine derivatives.</div></div>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":"23 21","pages":"Pages 5111-5115"},"PeriodicalIF":2.9000,"publicationDate":"2025-04-26","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/S1477052025003532","RegionNum":3,"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
Herein, we present an efficient and substrate/reagent-dependent annulation of amidines with 2-tert-amino benzaldehydes. When N-alkyl benzimidamides are employed, amidines undergo self-annulation to generate a hydrotriazine skeleton. In contrast, N-aryl benzimidamides yield quinazolines/hydroquinazolines under similar conditions. Additionally, the coupling of 2-tert-amino benzaldehydes with amidines under basic conditions yields 1,3,5-triazine derivatives.
期刊介绍:
Organic & Biomolecular Chemistry is an international journal using integrated research in chemistry-organic chemistry. Founded in 2003 by the Royal Society of Chemistry, the journal is published in Semimonthly issues and has been indexed by SCIE, a leading international database. The journal focuses on the key research and cutting-edge progress in the field of chemistry-organic chemistry, publishes and reports the research results in this field in a timely manner, and is committed to becoming a window and platform for rapid academic exchanges among peers in this field. The journal's impact factor in 2023 is 2.9, and its CiteScore is 5.5.