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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
[Image: see text] 1,2,6-Thiadiazines treated with visible light and (3)O(2) 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...
| Autores principales: | , , , , , , , , , , , , |
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| Formato: | Online Artículo Texto |
| Lenguaje: | English |
| Publicado: |
American Chemical Society
2023
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| Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10521009/ https://www.ncbi.nlm.nih.gov/pubmed/37695021 http://dx.doi.org/10.1021/acs.orglett.3c02673 |
| _version_ | 1785110048176865280 |
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| author | Broumidis, Emmanouil Thomson, Christopher G. Gallagher, Brendan Sotorríos, Lia McKendrick, Kenneth G. Macgregor, Stuart A. Paterson, Martin J. Lovett, Janet E. Lloyd, Gareth O. Rosair, Georgina M. Kalogirou, Andreas S. Koutentis, Panayiotis A. Vilela, Filipe |
| author_facet | Broumidis, Emmanouil Thomson, Christopher G. Gallagher, Brendan Sotorríos, Lia McKendrick, Kenneth G. Macgregor, Stuart A. Paterson, Martin J. Lovett, Janet E. Lloyd, Gareth O. Rosair, Georgina M. Kalogirou, Andreas S. Koutentis, Panayiotis A. Vilela, Filipe |
| author_sort | Broumidis, Emmanouil |
| collection | PubMed |
| description | [Image: see text] 1,2,6-Thiadiazines treated with visible light and (3)O(2) 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 (1)O(2) 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. |
| format | Online Article Text |
| id | pubmed-10521009 |
| institution | National Center for Biotechnology Information |
| language | English |
| publishDate | 2023 |
| publisher | American Chemical Society |
| record_format | MEDLINE/PubMed |
| spelling | pubmed-105210092023-09-27 The Photochemical Mediated Ring Contraction of 4H-1,2,6-Thiadiazines To Afford 1,2,5-Thiadiazol-3(2H)-one 1-Oxides Broumidis, Emmanouil Thomson, Christopher G. Gallagher, Brendan Sotorríos, Lia McKendrick, Kenneth G. Macgregor, Stuart A. Paterson, Martin J. Lovett, Janet E. Lloyd, Gareth O. Rosair, Georgina M. Kalogirou, Andreas S. Koutentis, Panayiotis A. Vilela, Filipe Org Lett [Image: see text] 1,2,6-Thiadiazines treated with visible light and (3)O(2) 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 (1)O(2) 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. American Chemical Society 2023-09-11 /pmc/articles/PMC10521009/ /pubmed/37695021 http://dx.doi.org/10.1021/acs.orglett.3c02673 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/). |
| spellingShingle | Broumidis, Emmanouil Thomson, Christopher G. Gallagher, Brendan Sotorríos, Lia McKendrick, Kenneth G. Macgregor, Stuart A. Paterson, Martin J. Lovett, Janet E. Lloyd, Gareth O. Rosair, Georgina M. Kalogirou, Andreas S. Koutentis, Panayiotis A. Vilela, Filipe The Photochemical Mediated Ring Contraction of 4H-1,2,6-Thiadiazines To Afford 1,2,5-Thiadiazol-3(2H)-one 1-Oxides |
| title | The Photochemical
Mediated Ring Contraction of 4H-1,2,6-Thiadiazines
To Afford 1,2,5-Thiadiazol-3(2H)-one 1-Oxides |
| title_full | The Photochemical
Mediated Ring Contraction of 4H-1,2,6-Thiadiazines
To Afford 1,2,5-Thiadiazol-3(2H)-one 1-Oxides |
| title_fullStr | The Photochemical
Mediated Ring Contraction of 4H-1,2,6-Thiadiazines
To Afford 1,2,5-Thiadiazol-3(2H)-one 1-Oxides |
| title_full_unstemmed | The Photochemical
Mediated Ring Contraction of 4H-1,2,6-Thiadiazines
To Afford 1,2,5-Thiadiazol-3(2H)-one 1-Oxides |
| title_short | The Photochemical
Mediated Ring Contraction of 4H-1,2,6-Thiadiazines
To Afford 1,2,5-Thiadiazol-3(2H)-one 1-Oxides |
| title_sort | photochemical
mediated ring contraction of 4h-1,2,6-thiadiazines
to afford 1,2,5-thiadiazol-3(2h)-one 1-oxides |
| url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10521009/ https://www.ncbi.nlm.nih.gov/pubmed/37695021 http://dx.doi.org/10.1021/acs.orglett.3c02673 |
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