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Synthesis of asymmetric 3,5-diaryl-4H-1,2,6-thiadiazin-4-ones via Suzuki-Miyaura and Stille coupling reactions

dc.contributor.authorIoannidou, Heraklidia A.en
dc.contributor.authorKoutentis, Panayiotis Andreasen
dc.creatorIoannidou, Heraklidia A.en
dc.creatorKoutentis, Panayiotis Andreasen
dc.date.accessioned2019-11-21T06:19:24Z
dc.date.available2019-11-21T06:19:24Z
dc.date.issued2012
dc.identifier.urihttp://gnosis.library.ucy.ac.cy/handle/7/55560
dc.description.abstractAsymmetric 3,5-diaryl substituted 4H-1,2,6-thiadiazin-4-ones can be prepared from 3,5-dichloro-4H-1,2,6-thiadiazin-4-one (1) via a multi-step protocol: selective nucleophilic mono-chloro substitution gives either the mono-methoxy or benzyloxy substituted mono-chlorothiadiazinones that can be phenylated via Suzuki-Miyaura coupling. Subsequent BBr 3 mediated dealkylation gives 3-hydroxy-5-phenyl-4H-1,2,6-thiadiazin-4-one (9) that can be activated by a modified Finkelstein halodehydroxylation via the triflate, enabling further arylation reactions using Suzuki-Miyaura or Stille coupling chemistry. © 2012 Elsevier Ltd. All rights reserved.en
dc.sourceTetrahedronen
dc.source.urihttps://www.scopus.com/inward/record.uri?eid=2-s2.0-84864289770&doi=10.1016%2fj.tet.2012.06.079&partnerID=40&md5=4007e59b615bad7d629258e22fe9cece
dc.subjectarticleen
dc.subjectpriority journalen
dc.subjectunclassified drugen
dc.subjectroom temperatureen
dc.subjectarylationen
dc.subjectnucleophilicityen
dc.subjectasymmetric synthesisen
dc.subjecthydrolysisen
dc.subjectreaction timeen
dc.subject2 benzyl 5 phenyl 2h 1,2,6 thiadiazine 3,4 dioneen
dc.subject3 (1 methyl 1h pyrrol 2 yl) 5 phenyl 4h 1,2,6 thiadiazin 4 oneen
dc.subject3 (2 methoxyphenyl) 5 phenyl 4h 1,2,6 thiadiazin 4 oneen
dc.subject3 (3 nitrophenyl) 5 phenyl 4h 1,2,6 thiadiazin 4 oneen
dc.subject3 (4 chlorophenyl) 5 phenyl 4h 1,2,6 thiadiazin 4 oneen
dc.subject3 (4 methoxyphenyl) 5 phenyl 4h 1,2,6 thiadiazin 4 oneen
dc.subject3 (benzyloxy) 5 chloro 4h 1,2,6 thiadiazin 4 oneen
dc.subject3 (benzyloxy) 5 phenyl 4h 1,2,6 thiadiazin 4 oneen
dc.subject3 (fur 2 yl) 5 phenyl 4h 1,2,6 thiadiazin 4 oneen
dc.subject3 bromo 5 phenyl 4h 1,2,6 thiadiazin 4 oneen
dc.subject3 chloro 5 methoxy 4h 1,2,6 thiadiazin 4 oneen
dc.subject3 chloro 5 phenyl 4h 1,2,6 thiadiazin 4 oneen
dc.subject3 hydroxy 5 phenyl 4h 1,2,6 thiadiazin 4 oneen
dc.subject3 iodo 5 phenyl 4h 1,2,6 thiadiazin 4 oneen
dc.subject3 methoxy 5 phenyl 4h 1,2,6 thiadiazin 4 oneen
dc.subject3 phenyl 5 (thien 2 yl) 4h 1,2,6 thiadiazin 4 oneen
dc.subject3 phenyl 5 trifluoromethanesulfonoxy 4h 1,2,6 thiadiazin 4 oneen
dc.subject3,5 diaryl 4h 1,2,6 thiadiazin 4 oneen
dc.subjectdealkylationen
dc.subjecthalogenationen
dc.subjecthydroxylationen
dc.subjectStille reactionen
dc.subjectSuzuki reactionen
dc.subjectSuzukie Miyaura reactionen
dc.subjecttetracyanoethyleneen
dc.subjectthiadiazine derivativeen
dc.subjecttrifluoroacetic aciden
dc.subjecttrifluoromethanesulfonic aciden
dc.titleSynthesis of asymmetric 3,5-diaryl-4H-1,2,6-thiadiazin-4-ones via Suzuki-Miyaura and Stille coupling reactionsen
dc.typeinfo:eu-repo/semantics/article
dc.identifier.doi10.1016/j.tet.2012.06.079
dc.description.volume68
dc.description.issue36
dc.description.startingpage7380
dc.description.endingpage7385
dc.author.faculty002 Σχολή Θετικών και Εφαρμοσμένων Επιστημών / Faculty of Pure and Applied Sciences
dc.author.departmentΤμήμα Χημείας / Department of Chemistry
dc.type.uhtypeArticleen
dc.description.notes<p>Cited By :5</p>en
dc.source.abbreviationTetrahedronen
dc.contributor.orcidKoutentis, Panayiotis Andreas [0000-0002-4652-7567]
dc.gnosis.orcid0000-0002-4652-7567


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