{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,28]],"date-time":"2026-03-28T09:36:52Z","timestamp":1774690612884,"version":"3.50.1"},"reference-count":25,"publisher":"MDPI AG","issue":"5","license":[{"start":{"date-parts":[[2019,3,10]],"date-time":"2019-03-10T00:00:00Z","timestamp":1552176000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001871","name":"Funda\u00e7\u00e3o para a Ci\u00eancia e a Tecnologia","doi-asserted-by":"publisher","award":["QOPNA research project (FCT UID\/QUI\/00062\/2019)"],"award-info":[{"award-number":["QOPNA research project (FCT UID\/QUI\/00062\/2019)"]}],"id":[{"id":"10.13039\/501100001871","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001871","name":"Funda\u00e7\u00e3o para a Ci\u00eancia e a Tecnologia","doi-asserted-by":"publisher","award":["CICECO-Aveiro Institute of Materials, POCI-01-0145-FEDER-007679 (FCT Ref. UID \/CTM \/50011\/2019)"],"award-info":[{"award-number":["CICECO-Aveiro Institute of Materials, POCI-01-0145-FEDER-007679 (FCT Ref. UID \/CTM \/50011\/2019)"]}],"id":[{"id":"10.13039\/501100001871","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001871","name":"Funda\u00e7\u00e3o para a Ci\u00eancia e a Tecnologia","doi-asserted-by":"publisher","award":["PT-DZ\/0005 and to the Portuguese NMR Network"],"award-info":[{"award-number":["PT-DZ\/0005 and to the Portuguese NMR Network"]}],"id":[{"id":"10.13039\/501100001871","id-type":"DOI","asserted-by":"publisher"}]},{"name":"General Directorate for Scientific Research and Technological Development \u2013 DGRSDT of Algeria and Agence Th\u00e9matique de Recherche en Sciences et Technologie ATRST","award":["bilateral project PT-DZ\/0005"],"award-info":[{"award-number":["bilateral project PT-DZ\/0005"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>The hemi-synthesis of chiral imine, benzimidazole and benzodiazepine structures is reported by the condensation of (S)-(\u2212)-perillaldehyde, the major phytochemical of Ammodaucus leucotrichus subsp. leucotrichus essential oil, with different amine derivatives of 2,3-diaminomaleonitrile, o-phenylenediamine and 3-[(2-aminoaryl)amino]dimedone. The reaction proceeds in situ at ambient temperature without prior isolation of the natural (S)-(\u2212)-perillaldehyde. Final products precipitate in the ethanolic reaction medium. 2D NMR and single-crystal X-ray diffraction studies were used to unequivocally characterize the structures in solution and in the solid state, respectively. Chiral HPLC analysis confirms the formation of unique enantiomers and diastereomeric mixtures.<\/jats:p>","DOI":"10.3390\/molecules24050975","type":"journal-article","created":{"date-parts":[[2019,3,12]],"date-time":"2019-03-12T03:49:31Z","timestamp":1552362571000},"page":"975","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":13,"title":["Hemi-Synthesis of Chiral Imine, Benzimidazole and Benzodiazepines from Essential Oil of Ammodaucus leucotrichus subsp. leucotrichus"],"prefix":"10.3390","volume":"24","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-2257-9028","authenticated-orcid":false,"given":"Farid","family":"Chebrouk","sequence":"first","affiliation":[{"name":"Laboratory of Biomathematics, Biochemistry, Biophysics and Scientometrics (L3BS), Faculty of Nature and Life Sciences (FSNV), University of Bejaia, 06000 Bejaia, Algeria"},{"name":"Research Center Scientific and Technical in Analyzes Physico-Chimiques CRAPC, BP384, Bou-Ismail, 42004 Tipaza, Algeria"}]},{"given":"Khodir","family":"Madani","sequence":"additional","affiliation":[{"name":"Laboratory of Biomathematics, Biochemistry, Biophysics and Scientometrics (L3BS), Faculty of Nature and Life Sciences (FSNV), University of Bejaia, 06000 Bejaia, Algeria"}]},{"given":"Brahim","family":"Cherfaoui","sequence":"additional","affiliation":[{"name":"Research Center Scientific and Technical in Analyzes Physico-Chimiques CRAPC, BP384, Bou-Ismail, 42004 Tipaza, Algeria"},{"name":"Laboratory of Applied Organic Chemistry, Faculty of Chemistry, University of Science and Technology Houari Boumediene, BP 32, Alia Bab-Ezzouar, 16111 Algiers, Algeria"}]},{"given":"Leila","family":"Boukenna","sequence":"additional","affiliation":[{"name":"Research Center Scientific and Technical in Analyzes Physico-Chimiques CRAPC, BP384, Bou-Ismail, 42004 Tipaza, Algeria"},{"name":"Laboratory of Applied Organic Chemistry, Faculty of Chemistry, University of Science and Technology Houari Boumediene, BP 32, Alia Bab-Ezzouar, 16111 Algiers, Algeria"}]},{"given":"M\u00f3nica","family":"V\u00e1lega","sequence":"additional","affiliation":[{"name":"QOPNA and LAQV-REQUIMTE, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal"}]},{"given":"Ricardo","family":"Mendes","sequence":"additional","affiliation":[{"name":"CICECO\u2014Aveiro Institute of Materials, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2051-5645","authenticated-orcid":false,"given":"Filipe","family":"Paz","sequence":"additional","affiliation":[{"name":"CICECO\u2014Aveiro Institute of Materials, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal"}]},{"given":"Khaldoun","family":"Bachari","sequence":"additional","affiliation":[{"name":"Research Center Scientific and Technical in Analyzes Physico-Chimiques CRAPC, BP384, Bou-Ismail, 42004 Tipaza, Algeria"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4064-3310","authenticated-orcid":false,"given":"Oualid","family":"Talhi","sequence":"additional","affiliation":[{"name":"Research Center Scientific and Technical in Analyzes Physico-Chimiques CRAPC, BP384, Bou-Ismail, 42004 Tipaza, Algeria"},{"name":"QOPNA and LAQV-REQUIMTE, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2861-8286","authenticated-orcid":false,"given":"Artur","family":"Silva","sequence":"additional","affiliation":[{"name":"QOPNA and LAQV-REQUIMTE, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal"}]}],"member":"1968","published-online":{"date-parts":[[2019,3,10]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"880","DOI":"10.1039\/c4np00010b","article-title":"Recreational drug discovery: natural products as lead structures for the synthesis of smart drugs","volume":"31","author":"Appendino","year":"2014","journal-title":"Nat. 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