{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,29]],"date-time":"2026-04-29T11:51:15Z","timestamp":1777463475811,"version":"3.51.4"},"reference-count":63,"publisher":"Wiley","issue":"12","license":[{"start":{"date-parts":[[2009,1,29]],"date-time":"2009-01-29T00:00:00Z","timestamp":1233187200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2009,3,9]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p><jats:bold>Careful metal selection<\/jats:bold>: Control of the reaction conditions of Cu<jats:sup>II<\/jats:sup> and Sn<jats:sup>IV<\/jats:sup> with Me<jats:sub>2<\/jats:sub>NNHCSNHPh permits the selective synthesis of metal complexes or a range of heterocyclic compounds generated by the oxidative coupling of two thiosemicarbazides (see figure).<jats:boxed-text content-type=\"graphic\" position=\"anchor\"><jats:graphic xmlns:xlink=\"http:\/\/www.w3.org\/1999\/xlink\" mimetype=\"image\/gif\" position=\"anchor\" specific-use=\"enlarged-web-image\" xlink:href=\"graphic\/mcontent.gif\"><jats:alt-text>magnified image<\/jats:alt-text><\/jats:graphic><\/jats:boxed-text><\/jats:p><jats:p>The reactions of 1,1\u2010dimethyl\u20104\u2010phenylthiosemicarbazide (LH) with Cu<jats:sup>II<\/jats:sup> and Sn<jats:sup>IV<\/jats:sup> have been investigated. If THF or methanol is used as solvent with Cu<jats:sup>II<\/jats:sup>, oxidative cyclisation and coupling are observed, yielding a 1,2,4\u2010thiadiazole or a 1,3,4\u2010thiadiazolium salt. SnI<jats:sub>4<\/jats:sub> is also able to induce oxidative coupling of two thiosemicarbazide ligands, yielding 1,2,4\u2010thiadiazolium or 1,2,4\u2010triazolium salts, with I<jats:sub>3<\/jats:sub><jats:sup>\u2212<\/jats:sup> as the counterion, depending on the reaction conditions. By contrast, reaction of LH with SnI<jats:sub>4<\/jats:sub> in acetone yields a 1,3\u2010thiazolium salt, with I<jats:sup>\u2212<\/jats:sup> as counterion. Reaction with Cu<jats:sup>II<\/jats:sup> salts or SnI<jats:sub>4<\/jats:sub> in basic media leads to the formation of metal complexes containing two deprotonated thiosemicarbazide ligands. In the reaction of CuCl<jats:sub>2<\/jats:sub> in water in the presence of acid a complex containing two neutral ligands is obtained. Reactions with SnCl<jats:sub>4<\/jats:sub> are not able to induce ligand cyclisation, although a coordination compound with two neutral ligands was isolated from methanol.<\/jats:p>","DOI":"10.1002\/chem.200801446","type":"journal-article","created":{"date-parts":[[2009,1,29]],"date-time":"2009-01-29T17:59:59Z","timestamp":1233251999000},"page":"3012-3023","source":"Crossref","is-referenced-by-count":12,"title":["Reactivity of Thiosemicarbazides with Redox Active Metal Ions: Controlled Formation of Coordination Complexes versus Heterocyclic Compounds"],"prefix":"10.1002","volume":"15","author":[{"given":"Elena","family":"L\u00f3pez\u2010Torres","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Jonathan\u2005R.","family":"Dilworth","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2009,2,26]]},"reference":[{"key":"e_1_2_7_1_2","doi-asserted-by":"publisher","DOI":"10.1002\/cbdv.200890073"},{"key":"e_1_2_7_2_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2006.01.034"},{"key":"e_1_2_7_3_2","doi-asserted-by":"publisher","DOI":"10.1016\/0010-8545(93)85052-6"},{"key":"e_1_2_7_4_2","doi-asserted-by":"publisher","DOI":"10.1007\/BF01062223"},{"key":"e_1_2_7_5_2","doi-asserted-by":"publisher","DOI":"10.1007\/3-540-53499-7_1"},{"key":"e_1_2_7_6_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.cct.2003.11.004"},{"key":"e_1_2_7_7_2","doi-asserted-by":"publisher","DOI":"10.1039\/B416296J"},{"key":"e_1_2_7_8_2","doi-asserted-by":"publisher","DOI":"10.1097\/00001813-199304000-00016"},{"key":"e_1_2_7_9_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm049529n"},{"key":"e_1_2_7_10_2","doi-asserted-by":"publisher","DOI":"10.2174\/1389557043487484"},{"key":"e_1_2_7_11_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jinorgbio.2006.01.037"},{"key":"e_1_2_7_12_2","doi-asserted-by":"publisher","DOI":"10.2174\/138161207779313768"},{"key":"e_1_2_7_13_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.nucmedbio.2007.01.002"},{"key":"e_1_2_7_14_2","first-page":"2034","volume":"47","author":"Wei L.","year":"2006","journal-title":"J. Nucl. Med."},{"key":"e_1_2_7_15_2","doi-asserted-by":"publisher","DOI":"10.1039\/b705989b"},{"key":"e_1_2_7_16_2","doi-asserted-by":"publisher","DOI":"10.1021\/ic0615628"},{"key":"e_1_2_7_17_2","doi-asserted-by":"publisher","DOI":"10.1039\/cc9960000097"},{"key":"e_1_2_7_18_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jinorgbio.2007.12.010"},{"key":"e_1_2_7_19_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jinorgbio.2005.10.002"},{"key":"e_1_2_7_20_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jorganchem.2005.12.025"},{"key":"e_1_2_7_21_2","doi-asserted-by":"publisher","DOI":"10.1002\/jat.1290"},{"key":"e_1_2_7_22_2","first-page":"1767","volume":"691","author":"Kovala\u2010Demertzi D.","year":"2006","journal-title":"J. Inorg. Biochem."},{"key":"e_1_2_7_23_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0141-3910(98)00176-1"},{"key":"e_1_2_7_24_2","doi-asserted-by":"publisher","DOI":"10.1002\/aoc.711"},{"key":"e_1_2_7_25_2","doi-asserted-by":"publisher","DOI":"10.1002\/mrc.975"},{"key":"e_1_2_7_26_2","doi-asserted-by":"publisher","DOI":"10.1039\/B512656H"},{"key":"e_1_2_7_27_2","doi-asserted-by":"publisher","DOI":"10.1021\/ic0514492"},{"key":"e_1_2_7_28_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm800031x"},{"key":"e_1_2_7_29_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200800539"},{"key":"e_1_2_7_30_2","doi-asserted-by":"publisher","DOI":"10.1007\/s11243-005-6354-7"},{"key":"e_1_2_7_31_2","doi-asserted-by":"publisher","DOI":"10.1039\/b401674b"},{"key":"e_1_2_7_32_2","doi-asserted-by":"publisher","DOI":"10.1002\/jhet.5570330353"},{"key":"e_1_2_7_33_2","doi-asserted-by":"publisher","DOI":"10.1002\/jhet.5570360315"},{"key":"e_1_2_7_34_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2004.07.060"},{"key":"e_1_2_7_35_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0223-5234(00)01176-4"},{"key":"e_1_2_7_36_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2004.02.008"},{"key":"e_1_2_7_37_2","doi-asserted-by":"publisher","DOI":"10.2174\/0929867043455738"},{"key":"e_1_2_7_38_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm049337s"},{"key":"e_1_2_7_39_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm980570y"},{"key":"e_1_2_7_40_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm960547h"},{"key":"e_1_2_7_41_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2004.05.021"},{"key":"e_1_2_7_42_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2007.01.006"},{"key":"e_1_2_7_43_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0161-813X(01)00064-X"},{"key":"e_1_2_7_44_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2007.03.033"},{"key":"e_1_2_7_45_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0022-2860(99)00374-9"},{"key":"e_1_2_7_46_2","doi-asserted-by":"publisher","DOI":"10.1039\/a807601d"},{"key":"e_1_2_7_47_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejic.200390106"},{"key":"e_1_2_7_48_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0020-1693(02)01257-4"},{"key":"e_1_2_7_49_2","doi-asserted-by":"publisher","DOI":"10.1039\/b617186a"},{"key":"e_1_2_7_50_2","doi-asserted-by":"publisher","DOI":"10.1039\/DT9840001349"},{"key":"e_1_2_7_51_2","doi-asserted-by":"publisher","DOI":"10.1039\/b405875e"},{"key":"e_1_2_7_52_2","doi-asserted-by":"publisher","DOI":"10.1021\/ic0496774"},{"key":"e_1_2_7_53_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejic.200400500"},{"key":"e_1_2_7_54_2","doi-asserted-by":"publisher","DOI":"10.1039\/B617136B"},{"key":"e_1_2_7_55_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.inoche.2005.07.005"},{"key":"e_1_2_7_56_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0020-1693(01)00654-5"},{"key":"e_1_2_7_57_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0022-328X(97)00680-3"},{"key":"e_1_2_7_58_2","volume-title":"Processing of X\u2010ray Diffraction Data Collected in Oscillating Mode, Methods Enzymol, Vol.\u2005276","author":"Otwinowski Z.","year":"1997"},{"key":"e_1_2_7_59_2","doi-asserted-by":"publisher","DOI":"10.1107\/S0021889894000221"},{"key":"e_1_2_7_60_2","doi-asserted-by":"publisher","DOI":"10.1107\/S0021889803021800"},{"key":"e_1_2_7_61_2","unstructured":"G.\u2005M. Sheldrick SAINT\u2010NT (version\u20056.04) SAX Area\u2010Detector Integration Program Bruker AXS Madison WI 1997\u20132001."},{"key":"e_1_2_7_62_2","unstructured":"Bruker AXS SHELXTL (version\u20056.10) Structure Determination Package Bruker AXS Madison WI 2000."},{"key":"e_1_2_7_63_2","doi-asserted-by":"publisher","DOI":"10.1107\/S0108767390000277"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fchem.200801446","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.200801446","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T19:01:35Z","timestamp":1760295695000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.200801446"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2009,2,26]]},"references-count":63,"journal-issue":{"issue":"12","published-print":{"date-parts":[[2009,3,9]]}},"alternative-id":["10.1002\/chem.200801446"],"URL":"https:\/\/doi.org\/10.1002\/chem.200801446","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2009,2,26]]}}}