dc.contributor.author | Christoforou, Irene C. | en |
dc.contributor.author | Kalogirou, Andreas S. | en |
dc.contributor.author | Koutentis, Panayiotis Andreas | en |
dc.creator | Christoforou, Irene C. | en |
dc.creator | Kalogirou, Andreas S. | en |
dc.creator | Koutentis, Panayiotis Andreas | en |
dc.date.accessioned | 2019-11-21T06:17:20Z | |
dc.date.available | 2019-11-21T06:17:20Z | |
dc.date.issued | 2009 | |
dc.identifier.uri | http://gnosis.library.ucy.ac.cy/handle/7/55324 | |
dc.description.abstract | Treatment of 1,2-bis(4-chloro-5H-1,2,3-dithiazol-5-ylidene)hydrazine 4 with benzyltriethylammonium iodide (1 equiv) affords dicyano-1,3,4-thiadiazole 3 and 5-cyano-1,3,4-thiadiazole-2-carboxamide 5 in 79 and 21% yields, respectively. By using polymer bound triphenylphosphine instead of benzyltriethylammonium iodide the dicyano-1,3,4-thiadiazole 3 can be isolated in 70% yield without chromatography. The reaction of DAMN with Appel salt 8 gave 2-(4-chloro-5H-1,2,3-dithiazol-5-ylideneamino)-2-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)acetonitrile 7 (14%), 2,3-bis-(4-chloro-5H-1,2,3-dithiazol-5-ylideneamino)fumaronitrile 10 (14%), and 2,3-bis(4-chloro-5H-1,2,3-dithiazol-5-ylideneamino)maleonitrile 11 (24%) together with other products. The maleonitrile 11 isomerizes into the fumaronitrile 10 on irradiation at 365 nm. Reaction of aminoacetonitrile with Appel salt 8 gives the (dithiazolylidene)acetonitrile 7 in 33% yield. Treatment of (dithiazolylidene)acetonitrile 7 with polymer bound triphenylphosphine gives tricyanothiazole 6 in 76% yield. A rational general mechanism for the transformation of bisdithiazoles to percyanoheteroles is proposed. © 2009 Elsevier Ltd. All rights reserved. | en |
dc.source | Tetrahedron | en |
dc.source.uri | https://www.scopus.com/inward/record.uri?eid=2-s2.0-70350454837&doi=10.1016%2fj.tet.2009.10.003&partnerID=40&md5=6b27d3404daadb5ff5634b4f21fdf5ba | |
dc.subject | article | en |
dc.subject | priority journal | en |
dc.subject | unclassified drug | en |
dc.subject | irradiation | en |
dc.subject | sodium chloride | en |
dc.subject | chemical structure | en |
dc.subject | polymer | en |
dc.subject | pyrrole derivative | en |
dc.subject | isomer | en |
dc.subject | iodide | en |
dc.subject | chromatography | en |
dc.subject | isomerization | en |
dc.subject | acetonitrile derivative | en |
dc.subject | (dithiazolylidene)acetonitrile | en |
dc.subject | 1,2 bis(4 chloro 5h 1,2,3 dithiazol 5 ylidene)hydrazine | en |
dc.subject | 1,2,3 dithiazole | en |
dc.subject | 2 (4 chloro 5h 1,2,3 dithiazol 5 ylideneamino) 2 (4 chloro 5h 1,2,3 dithiazol 5 ylidene)acetonitrile | en |
dc.subject | 2,3 bis (4 chloro 5h 1,2,3 dithiazol 5 ylideneamino)fumaronitrile | en |
dc.subject | 2,3 bis(4 chloro 5h 1,2,3 dithiazol 5 ylideneamino)maleonitrile | en |
dc.subject | 5 cyano 1,3,4 thiadiazole 2 carboxamide | en |
dc.subject | benzyltriethylammonium iodide | en |
dc.subject | dicyano 1,3,4 thiadiazole | en |
dc.subject | hydrazine derivative | en |
dc.subject | phosphine derivative | en |
dc.subject | thiadiazole derivative | en |
dc.subject | thiazole derivative | en |
dc.subject | tricyanothiazole | en |
dc.subject | triphenylphosphine | en |
dc.title | The preparation of dicyano-1,3,4-thiadiazole and tricyanothiazole via 1,2,3-dithiazole chemistry | en |
dc.type | info:eu-repo/semantics/article | |
dc.identifier.doi | 10.1016/j.tet.2009.10.003 | |
dc.description.volume | 65 | |
dc.description.issue | 48 | |
dc.description.startingpage | 9967 | |
dc.description.endingpage | 9972 | |
dc.author.faculty | 002 Σχολή Θετικών και Εφαρμοσμένων Επιστημών / Faculty of Pure and Applied Sciences | |
dc.author.department | Τμήμα Χημείας / Department of Chemistry | |
dc.type.uhtype | Article | en |
dc.description.notes | <p>Cited By :18</p> | en |
dc.source.abbreviation | Tetrahedron | en |
dc.contributor.orcid | Koutentis, Panayiotis Andreas [0000-0002-4652-7567] | |
dc.contributor.orcid | Christoforou, Irene C. [0000-0001-6624-3548] | |
dc.contributor.orcid | Kalogirou, Andreas S. [0000-0002-5476-5805] | |
dc.gnosis.orcid | 0000-0002-4652-7567 | |
dc.gnosis.orcid | 0000-0001-6624-3548 | |
dc.gnosis.orcid | 0000-0002-5476-5805 | |