{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,15]],"date-time":"2026-09-15T15:53:14Z","timestamp":1789487594212,"version":"build-2803163510"},"reference-count":35,"publisher":"American Chemical Society (ACS)","issue":"36","license":[{"start":{"date-parts":[[2026,9,1]],"date-time":"2026-09-01T00:00:00Z","timestamp":1788220800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by-nc-nd\/4.0\/"}],"funder":[{"DOI":"10.13039\/100008629","name":"South Dakota Board of Regents","doi-asserted-by":"publisher","id":[{"id":"10.13039\/100008629","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100017839","name":"South Dakota Governor's Office of Economic Development","doi-asserted-by":"publisher","id":[{"id":"10.13039\/100017839","id-type":"DOI","asserted-by":"publisher"}]},{"name":"SDSU Haarberg 3D Research Center"},{"name":"SDSU Research and Scholarly and Creative Activity"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,9,15]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>A single-step synthesis of the biologically active dihydropyrroloquinazolinone alkaloid natural products, S-(\u2212)- and R-(+)-vasicinone (5 and 6) has been developed for the first time. This reaction employs a POCl3-mediated coupling of methyl 2-aminobenzoate with either (S)- or (R)-3-hydroxypyrrolidin-2-one resulting in the synthesis of the two enantiomers in excellent yields. The enantiomeric excess (ee) was found to be &amp;gt;99% for both enantiomers and the specific rotations are consistent with the literature values. The reaction can be successfully extended to obtain diverse quinazolinone scaffolds such as substituted benzenoids, naphthalenes, indoles, thiophenes, phenylthiophenes, piperidines, oxazepines, and isoindolinones. We applied this reaction to the synthesis of our orally active antileishmanial lead peganine, and reduction of S-(\u2212)-vasicinone led to a conformationally more flexible analogue, 3a,4-dihydropeganine (28).<\/jats:p>","DOI":"10.1021\/acsomega.6c06741","type":"journal-article","created":{"date-parts":[[2026,9,3]],"date-time":"2026-09-03T07:55:29Z","timestamp":1788422129000},"page":"54521-54531","source":"Crossref","is-referenced-by-count":0,"title":["One-Step Synthesis\nof Dihydropyrroloquinazolinone\nAlkaloid Natural Products:\n                    <i>S<\/i>\n                    -(\u2212)- and\n                    <i>R<\/i>\n                    -(+)-Vasicinone and Their Novel Analogues"],"prefix":"10.1021","volume":"11","author":[{"ORCID":"https:\/\/orcid.org\/0009-0002-1719-6866","authenticated-orcid":true,"given":"Tanvir","family":"Khaliq","sequence":"first","affiliation":[{"name":"South Dakota State University , , , ,","place":["Brookings, South Dakota, United States, 57007"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Veerpal","family":"Kaur","sequence":"additional","affiliation":[{"name":"South Dakota State University , , , ,","place":["Brookings, South Dakota, United States, 57007"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,9,1]]},"reference":[{"key":"2026091510075777600_cit1","doi-asserted-by":"publisher","first-page":"25","DOI":"10.1016\/0957-4166(95)00412-2","article-title":"Reversal\nof absolute stereochemistry of the pyrrolo[2,1-b]quinazoline alkaloids\nvasicine, vasicinone, vasicinol and vasicinolone","volume":"7","author":"Joshi","year":"1996","journal-title":"Tetrahedron: Asymmetry"},{"key":"2026091510075777600_cit2","doi-asserted-by":"publisher","first-page":"118018","DOI":"10.1016\/j.bmc.2024.118018","article-title":"Alkaloids from Mackinlaya species\nand synthetic mackinazolinone derivatives: an overview","volume":"117","author":"Jaouen","year":"2025","journal-title":"Bioorg. 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Chemother."},{"key":"2026091510075777600_cit29","doi-asserted-by":"publisher","first-page":"5141","DOI":"10.1021\/jm5000408","article-title":"Antileishmanial activity of a series\nof N2, N4-disubstituted\nquinazoline-2,4-diamines","volume":"57","author":"Van Horn","year":"2014","journal-title":"J. Med. Chem."},{"key":"2026091510075777600_cit30","doi-asserted-by":"publisher","first-page":"5182","DOI":"10.1016\/j.bmc.2015.02.020","article-title":"SAR refinement\nof antileishmanial N2, N4-disubstituted\nquinazoline-2,4-diamines","volume":"23","author":"Zhu","year":"2015","journal-title":"Bioorg. Med. 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