{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,30]],"date-time":"2025-10-30T06:25:37Z","timestamp":1761805537525,"version":"3.41.2"},"reference-count":29,"publisher":"Frontiers Media SA","license":[{"start":{"date-parts":[[2023,5,25]],"date-time":"2023-05-25T00:00:00Z","timestamp":1684972800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001691","name":"Japan Society for the Promotion of Science","doi-asserted-by":"publisher","award":["JP22H02124 JP22J14638"],"award-info":[{"award-number":["JP22H02124 JP22J14638"]}],"id":[{"id":"10.13039\/501100001691","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["frontiersin.org"],"crossmark-restriction":true},"short-container-title":["Front. Chem."],"abstract":"<jats:p>Despite the promising pharmacological activity and material properties of five-membered heterocyclic compounds containing phosphorus and nitrogen, synthetic examples of them have been rather limited due to the instability of phosphorus toward air and water. In this study, 1,3-benzoazaphosphol analogues were selected as target molecules, and various synthetic routes were examined to establish a fundamental technology for the introduction of phosphorus groups into aromatic rings and formation of five-membered rings containing phosphorus and nitrogen by cyclization. As a result, we found that 2-aminophenyl(phenyl)phosphine is an extremely promising synthetic intermediate with high stability and easy handling. Furthermore, 2-methyl-3-phenyl-2,3-dihydro-1<jats:italic>H<\/jats:italic>-benzo[<jats:italic>d<\/jats:italic>][1,3]azaphosphole and 3-phenyl-2,3-dihydro-1<jats:italic>H<\/jats:italic>-benzo[<jats:italic>d<\/jats:italic>][1,3]azaphosphole-2-thione as synthetically useful 1,3-benzoazaphosphol analogues were successfully synthesized by using 2-aminophenyl(phenyl)phosphine as a key intermediate.<\/jats:p>","DOI":"10.3389\/fchem.2023.1174895","type":"journal-article","created":{"date-parts":[[2023,5,25]],"date-time":"2023-05-25T04:14:52Z","timestamp":1684988092000},"update-policy":"https:\/\/doi.org\/10.3389\/crossmark-policy","source":"Crossref","is-referenced-by-count":4,"title":["Practical synthesis of 1,3-benzoazaphosphole analogues"],"prefix":"10.3389","volume":"11","author":[{"given":"Yuki","family":"Yamamoto","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Soichiro","family":"Mita","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yuki","family":"Sato","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Kentaro","family":"Yano","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Akiya","family":"Ogawa","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1965","published-online":{"date-parts":[[2023,5,25]]},"reference":[{"key":"B1","doi-asserted-by":"publisher","first-page":"264","DOI":"10.1055\/s-1999-3394","article-title":"1H-1,3-Benzazaphospholes the organometallic route and a new three-step synthesis with reductive ring closure","volume":"1999","author":"Bansal","year":"1999","journal-title":"Synthesis"},{"key":"B2","doi-asserted-by":"publisher","first-page":"442","DOI":"10.3762\/bjoc.7.57","article-title":"An overview of the key routes to the best selling 5-membered ring heterocyclic pharmaceuticals","volume":"7","author":"Baumann","year":"2011","journal-title":"Beilstein J. 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