{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,5,6]],"date-time":"2026-05-06T00:52:03Z","timestamp":1778028723297,"version":"3.51.4"},"reference-count":32,"publisher":"Wiley","issue":"7","license":[{"start":{"date-parts":[[2025,2,28]],"date-time":"2025-02-28T00:00:00Z","timestamp":1740700800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"},{"start":{"date-parts":[[2025,2,28]],"date-time":"2025-02-28T00:00:00Z","timestamp":1740700800000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["ChemistryOpen"],"published-print":{"date-parts":[[2025,7]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>The present study focuses on the iodination of pyrazoles mediated by cadmium (II) acetate. The objects of research were compounds with pyrazole rings substituted by N\u2010propargyl, C, N\u2010alkyl groups. Depending on the molar ratios of the reagents effective ways of obtaining mono\u2010 and triiodo\u2010substituted products with the participation of the propargylic fragment in DMSO were elucidated. Induced by the cadmium (II) acetate principles of electrophilic iodination of the C\u20104 position of the pyrazole ring containing electron\u2010donating groups were revealed. The iodination of the pyrazole derivative with only propargylic substituent was found to target the CH\u2010acidic center of the triple bond and to lead to the corresponding iodoalkyne. An iodo\u2010substituted product with triple bond is more reactive and prone to further electrophilic iodination forming a triiodo\u2010substituted derivative. The introduction of methyl groups in the pyrazole ring of derivatives with propargylic substituent contributed to the promotion of competitive iodination reactions due to the increase in nucleophilicity of the pyrazole ring. Dimerized pyrazole rings with carbon atoms in the 4\u2010th position did not succeed in being iodinated by the mentioned way. Possible pathways for both triple bond and pyrazole ring iodination involving acetyl hypoiodite were proposed.<\/jats:p>","DOI":"10.1002\/open.202400443","type":"journal-article","created":{"date-parts":[[2025,3,12]],"date-time":"2025-03-12T01:24:53Z","timestamp":1741742693000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Efficient Regioselective Iodination of Pyrazole Derivatives Mediated by Cadmium(II) Acetate"],"prefix":"10.1002","volume":"14","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-6137-4530","authenticated-orcid":false,"given":"Nina G.","family":"Hobosyan","sequence":"first","affiliation":[{"name":"Department of Organic Chemistry Scientific Technological Center of Organic and Pharmaceutical Chemistry National Academy of Sciences of the Republic of Armenia  26 Azatutyan Ave. Yerevan Republic of Armenia"},{"name":"Department of Pharmaceutical Chemistry Yerevan Haybusak University  6 Abelyan Str. Yerevan Republic of Armenia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9003-747X","authenticated-orcid":false,"given":"Kristine V.","family":"Balyan","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry Scientific Technological Center of Organic and Pharmaceutical Chemistry National Academy of Sciences of the Republic of Armenia  26 Azatutyan Ave. Yerevan Republic of Armenia"},{"name":"Department of Pharmaceutical Chemistry International Scientific Educational Center of NAS RA  24\u2005M. Baghramyan Ave. Yerevan Republic of Armenia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2479-264X","authenticated-orcid":false,"given":"Lusine A.","family":"Movsisyan","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry Scientific Technological Center of Organic and Pharmaceutical Chemistry National Academy of Sciences of the Republic of Armenia  26 Azatutyan Ave. Yerevan Republic of Armenia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6026-4513","authenticated-orcid":false,"given":"Varduhi S.","family":"Hovsepyan","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry Scientific Technological Center of Organic and Pharmaceutical Chemistry National Academy of Sciences of the Republic of Armenia  26 Azatutyan Ave. Yerevan Republic of Armenia"},{"name":"Department of Biology and Chemistry and their Teaching Methodology Armenian State Pedagogical University after Khachatur Abovyan  17 Tigran Mets Ave. Yerevan Republic of Armenia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3224-0549","authenticated-orcid":false,"given":"Armen G.","family":"Ayvazyan","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry Scientific Technological Center of Organic and Pharmaceutical Chemistry National Academy of Sciences of the Republic of Armenia  26 Azatutyan Ave. Yerevan Republic of Armenia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8311-6276","authenticated-orcid":false,"given":"Henrik A.","family":"Panosyan","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry Scientific Technological Center of Organic and Pharmaceutical Chemistry National Academy of Sciences of the Republic of Armenia  26 Azatutyan Ave. Yerevan Republic of Armenia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9790-2577","authenticated-orcid":false,"given":"Hovhannes S.","family":"Attaryan","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry Scientific Technological Center of Organic and Pharmaceutical Chemistry National Academy of Sciences of the Republic of Armenia  26 Azatutyan Ave. Yerevan Republic of Armenia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2721-0273","authenticated-orcid":false,"given":"Hmayak B.","family":"Sargsyan","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry Scientific Technological Center of Organic and Pharmaceutical Chemistry National Academy of Sciences of the Republic of Armenia  26 Azatutyan Ave. Yerevan Republic of Armenia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7981-0388","authenticated-orcid":false,"given":"Haykanush R.","family":"Pogosyan","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry Scientific Technological Center of Organic and Pharmaceutical Chemistry National Academy of Sciences of the Republic of Armenia  26 Azatutyan Ave. Yerevan Republic of Armenia"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2025,2,28]]},"reference":[{"key":"e_1_2_9_1_1","doi-asserted-by":"crossref","first-page":"8451","DOI":"10.1016\/j.tet.2011.09.029","volume":"67","author":"Guillou S.","year":"2011","journal-title":"Tetrahedron"},{"key":"e_1_2_9_1_2","doi-asserted-by":"crossref","first-page":"4665","DOI":"10.1016\/j.tetlet.2006.04.125","volume":"47","author":"G\u00e9rard A.-L.","year":"2006","journal-title":"Tetrahedron Lett."},{"key":"e_1_2_9_1_3","doi-asserted-by":"crossref","first-page":"4309","DOI":"10.1021\/jo800321p","volume":"73","author":"McLaughlin M.","year":"2008","journal-title":"J. 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