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The photochemical mediated ring contraction of 4H-1,2,6-thiadiazines to afford 1,2,5-thiadiazol-3(2H)-one 1-oxides

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dc.contributor.authorBroumidis, Emmanouil
dc.contributor.authorThomson, Christopher G.
dc.contributor.authorGallagher, Brendan
dc.contributor.authorSotorríos, Lia
dc.contributor.authorMcKendrick, Kenneth G.
dc.contributor.authorMacgregor, Stuart A.
dc.contributor.authorPaterson, Martin J.
dc.contributor.authorLovett, Janet E.
dc.contributor.authorLloyd, Gareth O.
dc.contributor.authorRosair, Georgina M.
dc.contributor.authorKalogirou, Andreas S.
dc.contributor.authorKoutentis, Panayiotis A.
dc.contributor.authorVilela, Filipe
dc.date.accessioned2023-09-11T15:30:02Z
dc.date.available2023-09-11T15:30:02Z
dc.date.issued2023-09-22
dc.identifier293803447
dc.identifiere2d32228-83e8-4b7a-a90e-4759cc7a3f5a
dc.identifier85172033929
dc.identifier001065993400001
dc.identifier37695021
dc.identifier.citationBroumidis , E , Thomson , C G , Gallagher , B , Sotorríos , L , McKendrick , K G , Macgregor , S A , Paterson , M J , Lovett , J E , Lloyd , G O , Rosair , G M , Kalogirou , A S , Koutentis , P A & Vilela , F 2023 , ' The photochemical mediated ring contraction of 4H-1,2,6-thiadiazines to afford 1,2,5-thiadiazol-3(2H)-one 1-oxides ' , Organic Letters , vol. 25 , no. 37 , pp. 6907-6912 . https://doi.org/10.1021/acs.orglett.3c02673en
dc.identifier.issn1523-7060
dc.identifier.otherRIS: urn:3AD20D80477927C69422FEA5C0C5BD7E
dc.identifier.otherORCID: /0000-0002-3561-450X/work/142499463
dc.identifier.urihttps://hdl.handle.net/10023/28350
dc.descriptionFunding: E.B. and C.G.T. are grateful to Heriot-Watt University and the EPSRC CRITICAT Centre for Doctoral Training (E.B. Ph.D. Studentship: EP/L016419/1, C.G.T Ph.D. Studentship: EP/LO14419/1) for funding and training. C.G.T. is grateful to the Heriot-Watt Annual Fund for financial support. P.A.K. and A.S.K. thank the University of Cyprus for the Internal Grant “Thiadiazine-Based Organic Photovoltaics”, and the Cyprus Research Promotion Foundation (Grant Nos. ΣΤΡΑΤΗΙΙ/0308/06, NEKYP/0308/02 ΥΓΕΙΑ/0506/19, and ΕΝΙΣΧ/0308/83). M.J.P. thanks the EPSRC for funding (Grant Nos. EP/T021675 and EP/V006746), and the Leverhulme Trust (Grant No. PG-2020-208). S.A.M. thanks the EPSRC for funding (Grant No. EP/T019867/1).en
dc.description.abstract1,2,6-Thiadiazines treated with visible light and 3O2 under ambient conditions are converted into difficult-to-access 1,2,5-thiadiazole 1-oxides (35 examples, yields of 39–100%). Experimental and theoretical studies reveal that 1,2,6-thiadiazines act as triplet photosensitizers that produce 1O2 and then undergo a chemoselective [3 + 2] cycloaddition to give an endoperoxide that ring contracts with selective carbon atom excision and complete atom economy. The reaction was optimized under both batch and continuous-flow conditions and is also efficient in green solvents.
dc.format.extent6
dc.format.extent1946760
dc.language.isoeng
dc.relation.ispartofOrganic Lettersen
dc.subjectQD Chemistryen
dc.subjectDASen
dc.subjectACen
dc.subjectMCCen
dc.subject.lccQDen
dc.titleThe photochemical mediated ring contraction of 4H-1,2,6-thiadiazines to afford 1,2,5-thiadiazol-3(2H)-one 1-oxidesen
dc.typeJournal articleen
dc.contributor.sponsorEPSRCen
dc.contributor.institutionUniversity of St Andrews. School of Physics and Astronomyen
dc.contributor.institutionUniversity of St Andrews. Biomedical Sciences Research Complexen
dc.identifier.doihttps://doi.org/10.1021/acs.orglett.3c02673
dc.description.statusPeer revieweden
dc.identifier.grantnumberEP/L016419/1en


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