{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,18]],"date-time":"2026-08-18T04:57:55Z","timestamp":1787029075686,"version":"build-2736575974"},"reference-count":27,"publisher":"MDPI AG","issue":"16","license":[{"start":{"date-parts":[[2022,8,18]],"date-time":"2022-08-18T00:00:00Z","timestamp":1660780800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"the College of Engineering (Startup Grant), Nanyang Technological University, Singapore","award":["G00003291"],"award-info":[{"award-number":["G00003291"]}]},{"name":"the College of Engineering (Startup Grant), Nanyang Technological University, Singapore","award":["31S401\/12S040\/Project #852"],"award-info":[{"award-number":["31S401\/12S040\/Project #852"]}]},{"name":"United Arab Emirates University (UAEU), Al-Ain","award":["G00003291"],"award-info":[{"award-number":["G00003291"]}]},{"name":"United Arab Emirates University (UAEU), Al-Ain","award":["31S401\/12S040\/Project #852"],"award-info":[{"award-number":["31S401\/12S040\/Project #852"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>A one-step, three-component reaction between \u03b1-hydroxyketones, oxoacetonitriles, and primary amines gives N-substituted 2,3,5-functionalized 3-cyanopyrroles with complete selectivity in up to 90% isolated yields. The reaction worked on a wide substrate scope under mild reaction conditions (AcOH as a catalyst, EtOH, 70 \u00b0C, 3 h). The reaction proceeded with very high atom efficiency as water is the only molecule lost during the reaction. The practicality of the reaction was demonstrated on a large gram scale. The structures of the 3-cyanopyrroles were confirmed by single-crystal X-ray diffraction and NMR; this work provides a general and practical entry to pyrrole scaffolds suitably decorated for the synthesis of various bioactive pyrroles in a concise manner.<\/jats:p>","DOI":"10.3390\/molecules27165285","type":"journal-article","created":{"date-parts":[[2022,8,18]],"date-time":"2022-08-18T23:28:41Z","timestamp":1660865321000},"page":"5285","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":6,"title":["Selective One-Pot Multicomponent Synthesis of N-Substituted 2,3,5-Functionalized 3-Cyanopyrroles via the Reaction between \u03b1-Hydroxyketones, Oxoacetonitriles, and Primary Amines"],"prefix":"10.3390","volume":"27","author":[{"given":"Mengxin","family":"Xia","sequence":"first","affiliation":[{"name":"School of Chemical and Biomedical Engineering, Nanyang Technological University, 62 Nanyang Drive, N1.2\u2013B1-14, Singapore 637459, Singapore"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3365-0451","authenticated-orcid":false,"given":"Ziad","family":"Moussa","sequence":"additional","affiliation":[{"name":"Department of Chemistry, College of Science, United Arab Emirates University, Al Ain P.O. Box 15551, United Arab Emirates"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zaher M. A.","family":"Judeh","sequence":"additional","affiliation":[{"name":"School of Chemical and Biomedical Engineering, Nanyang Technological University, 62 Nanyang Drive, N1.2\u2013B1-14, Singapore 637459, Singapore"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2022,8,18]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"13","DOI":"10.1016\/j.ejmech.2015.12.017","article-title":"Pyrrole: An emerging scaffold for construction of valuable therapeutic agents","volume":"110","author":"Gholap","year":"2016","journal-title":"Eur. J. Med. Chem."},{"key":"ref_2","doi-asserted-by":"crossref","unstructured":"Trofimov, B.A., Al\u2019bina, I.M., Schmidt, E.Y., and Sobenina, L.N. (2014). 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