{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T02:09:50Z","timestamp":1760234990084,"version":"build-2065373602"},"reference-count":15,"publisher":"MDPI AG","issue":"7","license":[{"start":{"date-parts":[[2021,7,6]],"date-time":"2021-07-06T00:00:00Z","timestamp":1625529600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Symmetry"],"abstract":"<jats:p>As a continuation of research on 1-vinylazulenes synthesis, on their physico\u2013chemical properties as well as on their use as colorimetric and electrochemical materials for the detection of heavy metals ions, new compounds, 4-(azulen-1-ylmethylene)-2-phenyloxazol-5(4H)-ones, are reported. The exceptional structure of azulene moiety with symmetrical electron distribution only with respect to the x-axis gives some special chemical and physical properties to compounds in which it is inserted. Various azulene-1-carbaldehydes and hippuric acids are condensed with good yields in Erlenmeyer\u2014Pl\u00f6chl reaction conditions. The obtained 1-vinylzulenes were characterized and their UV-Vis and NMR spectra were briefly discussed.<\/jats:p>","DOI":"10.3390\/sym13071209","type":"journal-article","created":{"date-parts":[[2021,7,6]],"date-time":"2021-07-06T02:59:47Z","timestamp":1625540387000},"page":"1209","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":8,"title":["1-Vinylazulenes with Oxazolonic Ring-Potential Ligands for Metal Ion Detectors; Synthesis and Products Properties"],"prefix":"10.3390","volume":"13","author":[{"given":"Mihaela","family":"Cristea","sequence":"first","affiliation":[{"name":"\u201cC.D. Nenitzescu\u201d Institute of Organic Chemistry, Romanian Academy, 202 B Spl. Independentei, P.O. Box 35-108, 060023 Bucharest, Romania"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Liviu","family":"B\u00eerzan","sequence":"additional","affiliation":[{"name":"\u201cC.D. Nenitzescu\u201d Institute of Organic Chemistry, Romanian Academy, 202 B Spl. Independentei, P.O. Box 35-108, 060023 Bucharest, Romania"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Florea","family":"Dumitrascu","sequence":"additional","affiliation":[{"name":"\u201cC.D. Nenitzescu\u201d Institute of Organic Chemistry, Romanian Academy, 202 B Spl. Independentei, P.O. Box 35-108, 060023 Bucharest, Romania"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Cristian","family":"Enache","sequence":"additional","affiliation":[{"name":"National Phytosanitary Laboratory, 077190 Voluntari, Romania"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Victorita","family":"Tecuceanu","sequence":"additional","affiliation":[{"name":"\u201cC.D. Nenitzescu\u201d Institute of Organic Chemistry, Romanian Academy, 202 B Spl. Independentei, P.O. Box 35-108, 060023 Bucharest, Romania"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0433-752X","authenticated-orcid":false,"given":"Anamaria","family":"Hanganu","sequence":"additional","affiliation":[{"name":"\u201cC.D. Nenitzescu\u201d Institute of Organic Chemistry, Romanian Academy, 202 B Spl. Independentei, P.O. Box 35-108, 060023 Bucharest, Romania"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Constantin","family":"Dr\u0103ghici","sequence":"additional","affiliation":[{"name":"\u201cC.D. Nenitzescu\u201d Institute of Organic Chemistry, Romanian Academy, 202 B Spl. Independentei, P.O. Box 35-108, 060023 Bucharest, Romania"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8206-5227","authenticated-orcid":false,"given":"C\u0103lin","family":"Deleanu","sequence":"additional","affiliation":[{"name":"\u201cC.D. Nenitzescu\u201d Institute of Organic Chemistry, Romanian Academy, 202 B Spl. Independentei, P.O. Box 35-108, 060023 Bucharest, Romania"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7022-8893","authenticated-orcid":false,"given":"Alina","family":"Nicolescu","sequence":"additional","affiliation":[{"name":"\u201cC.D. Nenitzescu\u201d Institute of Organic Chemistry, Romanian Academy, 202 B Spl. Independentei, P.O. Box 35-108, 060023 Bucharest, Romania"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Maria","family":"Maganu","sequence":"additional","affiliation":[{"name":"\u201cC.D. Nenitzescu\u201d Institute of Organic Chemistry, Romanian Academy, 202 B Spl. Independentei, P.O. Box 35-108, 060023 Bucharest, Romania"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Alexandru C.","family":"Razus","sequence":"additional","affiliation":[{"name":"\u201cC.D. Nenitzescu\u201d Institute of Organic Chemistry, Romanian Academy, 202 B Spl. Independentei, P.O. Box 35-108, 060023 Bucharest, Romania"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2021,7,6]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","unstructured":"Razus, A. (2021). Azulene Moiety as Electron Reservoir in Positively Charged Systems; A Short Survey. Symmetry, 13.","DOI":"10.3390\/sym13040526"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"471","DOI":"10.1021\/acs.accounts.5b00523","article-title":"Out of the Blue! Azuliporphyrins and Related Carbaporphyrinoid Systems","volume":"49","author":"Lash","year":"2016","journal-title":"Acc. Chem. Res."},{"key":"ref_3","unstructured":"Churchill, M.R. (2007). Transition Metal Complexes of Azulene and Related Ligands, Wiley."},{"key":"ref_4","first-page":"489","article-title":"Synthesis of ligands based on azulene derivatives used as metal sensors","volume":"62","author":"Birzan","year":"2017","journal-title":"Rev. Roum. Chim."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"76","DOI":"10.1139\/v86-015","article-title":"Electrically conducting polymers: A review of the electropolymerization reaction, of the effects of chemical structure on polymer film properties, and of applications towards technology","volume":"64","author":"Waltman","year":"1986","journal-title":"Can. J. Chem."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"3222","DOI":"10.1021\/ma035335q","article-title":"Stimuli-Responsive Conjugated Copolymers Having Electro-Active Azulene and Bithiophene Units in the Polymer Skeleton: Effect of Protonation and p-Doping on Conducting Properties","volume":"37","author":"Wang","year":"2004","journal-title":"Macromolecules"},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"5028","DOI":"10.1016\/j.electacta.2011.03.096","article-title":"Films of poly(4-azulen-1-yl-2,6-bis(2-thienyl)pyridine) for heavy metal ions complexation","volume":"56","author":"Buica","year":"2011","journal-title":"Electrochim. Acta"},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"93","DOI":"10.1002\/elan.201600503","article-title":"Modified Electrodes Based on Poly[(2E)-2-(Azulen-1-ylmethylidene)hydrazinecarbothioamide] for Heavy Metal Ions Complexation","volume":"29","author":"Buica","year":"2017","journal-title":"Electroanalysis"},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"2316","DOI":"10.1016\/j.tet.2016.03.049","article-title":"1-vinylazulenes\u2013potential host molecules in ligands for metal ion detectors","volume":"72","author":"Birzan","year":"2016","journal-title":"Tetrahedron"},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"31","DOI":"10.3998\/ark.5550190.0010.b04","article-title":"Synthesis and properties of azulene-containing 1,3-dioxanes","volume":"2009","author":"Razus","year":"2009","journal-title":"Arkivoc"},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"246","DOI":"10.1016\/j.dyepig.2016.02.033","article-title":"Vinylazulenes chromophores: Synthesis and characterization","volume":"131","author":"Birzan","year":"2016","journal-title":"Dye. Pigment"},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"73","DOI":"10.5599\/jese.475","article-title":"DFT calculations and electrochemical studies on azulene ligands for heavy metal ions detection using chemically modified electrodes","volume":"8","author":"Stefaniu","year":"2018","journal-title":"J. Electrochem. Sci. Eng."},{"key":"ref_13","doi-asserted-by":"crossref","unstructured":"Ungureanu, E.-M., Apostoiu, M.P., Arnold, G.-L.T., Birzan, L., Isopescu, R., Stanciu, G., and Buica, G.-O. (2021). Electrochemical Comparison on New (Z)-5-(Azulen-1-Ylmethylene)-2-Thioxo-Thiazolidin-4-Ones. Symmetry, 13.","DOI":"10.3390\/sym13040588"},{"key":"ref_14","doi-asserted-by":"crossref","unstructured":"Wang, Z. (2010). Erlenmeyer-Pl\u00f6chl Azlactone Synthesis. Comprehensive Organic Name Reactions and Reagents, John Wiley & Sons, Inc.","DOI":"10.1002\/9780470638859"},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"1131","DOI":"10.1021\/om00095a019","article-title":"Tellurapyrylium dyes. The electron-donating properties of the chalcogen atoms to the chalcogenapyrylium nuclei and their radical dications, neutral radicals, and anions","volume":"7","author":"Detty","year":"1988","journal-title":"Organometallics"}],"container-title":["Symmetry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/2073-8994\/13\/7\/1209\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T06:26:27Z","timestamp":1760163987000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/2073-8994\/13\/7\/1209"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,7,6]]},"references-count":15,"journal-issue":{"issue":"7","published-online":{"date-parts":[[2021,7]]}},"alternative-id":["sym13071209"],"URL":"https:\/\/doi.org\/10.3390\/sym13071209","relation":{},"ISSN":["2073-8994"],"issn-type":[{"type":"electronic","value":"2073-8994"}],"subject":[],"published":{"date-parts":[[2021,7,6]]}}}