{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,6]],"date-time":"2026-10-06T18:43:15Z","timestamp":1791312195560,"version":"4.3.1"},"reference-count":19,"publisher":"Frontiers Media SA","license":[{"start":{"date-parts":[[2023,9,29]],"date-time":"2023-09-29T00:00:00Z","timestamp":1695945600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":["frontiersin.org"],"crossmark-restriction":true},"short-container-title":["Front. Chem."],"abstract":"<jats:p>Herein we report a copper-catalyzed synthesis of imidazolidine by employing the reaction of aziridine with imine. The reaction smoothly provided a diverse range of 2-substituted imidazolidines with high compatibility with various functional groups. Moreover, during our investigation, we discovered that isocyanate also reacted with aziridine to yield substituted imidazolidinones efficiently. The versatility of these reactions was further demonstrated by their application in the synthesis of hybrid molecules derived from two pharmaceutical compounds. This approach opens new possibilities for the discovery of novel classes of bioactive molecules.<\/jats:p>","DOI":"10.3389\/fchem.2023.1272034","type":"journal-article","created":{"date-parts":[[2023,9,29]],"date-time":"2023-09-29T12:04:07Z","timestamp":1695989047000},"update-policy":"https:\/\/doi.org\/10.3389\/crossmark-policy","source":"Crossref","is-referenced-by-count":10,"title":["Copper-catalyzed reaction of aziridine for the synthesis of substituted imidazolidine and imidazolidinone"],"prefix":"10.3389","volume":"11","author":[{"given":"Kota","family":"Hashimoto","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Daiki","family":"Higuchi","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Satoshi","family":"Matsubara","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kei","family":"Murakami","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1965","published-online":{"date-parts":[[2023,9,29]]},"reference":[{"key":"B1","doi-asserted-by":"publisher","first-page":"230","DOI":"10.1177\/0003319707304580","article-title":"Comparison of monotherapy versus combination antihypertensive therapy in elderly patients with essential hypertension","volume":"59","author":"Antonopoulos","year":"2008","journal-title":"Angiology"},{"key":"B2","doi-asserted-by":"publisher","first-page":"3511","DOI":"10.1016\/j.bmc.2019.07.005","article-title":"1,2,3-Triazole-containing hybrids as leads in medicinal chemistry: A recent overview","volume":"27","author":"Bozorov","year":"2019","journal-title":"Bioorg. Med. Chem."},{"key":"B3","doi-asserted-by":"publisher","first-page":"e202301071","DOI":"10.1002\/chem.202301071","article-title":"Copper-catalyzed heterocyclic recombination of aziridine and diazetidine for the synthesis of imidazolidine","volume":"29","author":"Higuchi","year":"2023","journal-title":"Chem. Eur. J."},{"key":"B4","doi-asserted-by":"publisher","first-page":"92","DOI":"10.1021\/acs.orglett.7b03448","article-title":"Oxidative dehydrogenative [2 + 3]-cyclization of Glycine esters with aziridines leading to imidazolidines","volume":"20","author":"Li","year":"2018","journal-title":"Org. Lett."},{"key":"B5","doi-asserted-by":"publisher","first-page":"3587","DOI":"10.1021\/acs.orglett.8b01378","article-title":"Chirality transfer in rhodium(I)-Catalyzed [3 + 2]-cycloaddition of vinyl aziridines and oxime ethers: Atom-economical synthesis of chiral imidazolidines","volume":"20","author":"Lin","year":"2018","journal-title":"Org. Lett."},{"key":"B6","doi-asserted-by":"publisher","first-page":"1858","DOI":"10.1021\/acs.orglett.7b00600","article-title":"Metal-free [2 + 1 + 2]-cycloaddition of tosylhydrazones with hexahydro-1,3,5-triazines to form imidazolidines","volume":"19","author":"Liu","year":"2017","journal-title":"Org. Lett."},{"key":"B7","doi-asserted-by":"publisher","first-page":"4112","DOI":"10.1021\/jacs.1c00228","article-title":"Diastereodivergent intermolecular 1,2-diamination of unactivated alkenes enabled by iodine catalysis","volume":"143","author":"Minakata","year":"2021","journal-title":"J. Am. Chem. Soc."},{"key":"B8","doi-asserted-by":"publisher","first-page":"15387","DOI":"10.1002\/chem.202102748","article-title":"Primary sulfonamide functionalization via sulfonyl pyrroles: Seeing the N-ts bond in a different light","volume":"27","author":"Ozaki","year":"2021","journal-title":"Chem. Eur. J."},{"key":"B9","doi-asserted-by":"publisher","first-page":"6859","DOI":"10.1002\/ejoc.202000688","article-title":"Copper in efficient synthesis of aromatic heterocycles with single heteroatom","volume":"2020","author":"Pal","year":"2020","journal-title":"Eur. J. Org. Chem."},{"key":"B10","doi-asserted-by":"publisher","first-page":"2643","DOI":"10.1002\/ejoc.201901853","article-title":"The binomial copper-catalysis and asymmetric ring opening of strained heterocycles: Past and future challenges","volume":"2020","author":"Pineschi","year":"2020","journal-title":"Eur. J. Org. Chem."},{"key":"B11","doi-asserted-by":"publisher","first-page":"7903","DOI":"10.1021\/acs.orglett.0c02801","article-title":"Stereoselective synthesis of hexahydroimidazo[1,2-a]quinolines via SN2-type ring-opening hydroarylation\u2013hydroamination cascade cyclization of activated aziridines with N-propargylanilines","volume":"22","author":"Pradhan","year":"2020","journal-title":"Org. Lett."},{"key":"B12","doi-asserted-by":"publisher","first-page":"158","DOI":"10.1021\/acs.orglett.6b03458","article-title":"Stereospecific copper-catalyzed domino ring opening and sp3 C\u2212H functionalization of activated aziridines with N-alkylanilines","volume":"19","author":"Sengoden","year":"2017","journal-title":"Org. Lett."},{"key":"B13","doi-asserted-by":"publisher","first-page":"2619","DOI":"10.1002\/adsc.202001569","article-title":"Synthesis of diversely substituted imidazolidines via [3+2] cycloaddition of 1,3,5\u2010triazinanes with donor\u2010acceptor aziridines and their anti\u2010tumor activity","volume":"363","author":"Shi","year":"2021","journal-title":"Adv. Synth. Catal."},{"key":"B14","doi-asserted-by":"publisher","first-page":"413","DOI":"10.1016\/s0022-3476(99)70197-6","article-title":"Comparison of a \u03b2-lactam alone versus \u03b2-lactam and an aminoglycoside for pulmonary exacerbation in cystic fibrosis","volume":"134","author":"Smith","year":"1999","journal-title":"J. Pediatr."},{"key":"B15","doi-asserted-by":"publisher","first-page":"1444","DOI":"10.1021\/acs.orglett.8b00228","article-title":"Diastereoselective palladium-catalyzed (3 + 2)-cycloadditions from cyclic imines and vinyl aziridines","volume":"20","author":"Spielmann","year":"2018","journal-title":"Org. Lett."},{"key":"B16","doi-asserted-by":"publisher","first-page":"11161","DOI":"10.1021\/acs.joc.9b01959","article-title":"Access to imidazolidines via 1,3-dipolar cycloadditions of 1,3,5-triazinanes with aziridines","volume":"84","author":"Tu","year":"2019","journal-title":"J. Org. Chem."},{"key":"B17","doi-asserted-by":"publisher","first-page":"2147","DOI":"10.1055\/s-0031-1290816","article-title":"Y(OTf)3-Catalyzed diastereoselective [3+2] cycloaddition of N-tosylaziridines and imines; efficient synthesis of multisubstituted imidazolidines","volume":"44","author":"Wu","year":"2012","journal-title":"Synthesis"},{"key":"B18","doi-asserted-by":"publisher","first-page":"1640","DOI":"10.1039\/d1cs00727k","article-title":"Copper-catalyzed radical relay in C(sp3)\u2013H functionalization","volume":"51","author":"Zhang","year":"2022","journal-title":"Chem. Soc. Rev."},{"key":"B19","doi-asserted-by":"publisher","first-page":"4504","DOI":"10.1039\/c5cs00882d","article-title":"Copper-catalyzed oxidative carbon\u2013heteroatom bond formation: A recent update","volume":"45","author":"Zhu","year":"2016","journal-title":"Chem. Soc. Rev."}],"container-title":["Frontiers in Chemistry"],"original-title":[],"link":[{"URL":"https:\/\/www.frontiersin.org\/articles\/10.3389\/fchem.2023.1272034\/full","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,9,29]],"date-time":"2023-09-29T12:04:17Z","timestamp":1695989057000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.frontiersin.org\/articles\/10.3389\/fchem.2023.1272034\/full"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,9,29]]},"references-count":19,"alternative-id":["10.3389\/fchem.2023.1272034"],"URL":"https:\/\/doi.org\/10.3389\/fchem.2023.1272034","relation":{},"ISSN":["2296-2646"],"issn-type":[{"value":"2296-2646","type":"electronic"}],"subject":[],"published":{"date-parts":[[2023,9,29]]},"article-number":"1272034"}}