Unprecedented visible light-initiated topochemical [2 + 2] cycloaddition in a functionalized bimane dye
Bimanes, a class of molecules based on the 1H,7H-pyrazolo[1,2-a]pyrazole-1,7-dione scaffold, were first introduced by E. M. Kosower in 1978. In this study, we report the topochemical cycloaddition of diethyl 2,6-dichloro-1,7-dioxo-1H,7H-pyrazolo[1,2-a]pyrazole-3,5-dicarboxylate (Cl2B), initiated by...
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| Language: | English |
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Beilstein-Institut
2025-03-01
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| Series: | Beilstein Journal of Organic Chemistry |
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| Online Access: | https://doi.org/10.3762/bjoc.21.37 |
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| author | Metodej Dvoracek Brendan Twamley Mathias O. Senge Mikhail A. Filatov |
| author_facet | Metodej Dvoracek Brendan Twamley Mathias O. Senge Mikhail A. Filatov |
| author_sort | Metodej Dvoracek |
| collection | DOAJ |
| description | Bimanes, a class of molecules based on the 1H,7H-pyrazolo[1,2-a]pyrazole-1,7-dione scaffold, were first introduced by E. M. Kosower in 1978. In this study, we report the topochemical cycloaddition of diethyl 2,6-dichloro-1,7-dioxo-1H,7H-pyrazolo[1,2-a]pyrazole-3,5-dicarboxylate (Cl2B), initiated by visible light. Crystal structure analysis confirmed that the reactive double bonds are parallel and coplanar, in line with the Schmidt criteria for topochemical cycloaddition. Additionally, two other bimane derivatives with different substitution patterns were synthesized and investigated. Our findings suggest that functionalizing bimanes to redshift their absorption maxima into the visible-light spectrum provides a promising strategy for synthesizing substituted cyclobutanes without the need for ultraviolet irradiation. |
| format | Article |
| id | doaj-art-ae67dbda34874427a6721ede5d23dd52 |
| institution | OA Journals |
| issn | 1860-5397 |
| language | English |
| publishDate | 2025-03-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj-art-ae67dbda34874427a6721ede5d23dd522025-08-20T02:08:15ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972025-03-0121150050910.3762/bjoc.21.371860-5397-21-37Unprecedented visible light-initiated topochemical [2 + 2] cycloaddition in a functionalized bimane dyeMetodej Dvoracek0Brendan Twamley1Mathias O. Senge2Mikhail A. Filatov3School of Chemical and Biopharmaceutical Sciences, Technological University Dublin, City Campus, Grangegorman, D07 ADY7 Dublin, Ireland School of Chemistry, Trinity College Dublin, The University of Dublin, Dublin 2, Ireland, School of Chemistry, Trinity College Dublin, The University of Dublin, Trinity Biomedical Sciences Institute, 152-160 Pearse Street, Dublin D02 R590, Ireland School of Chemical and Biopharmaceutical Sciences, Technological University Dublin, City Campus, Grangegorman, D07 ADY7 Dublin, Ireland Bimanes, a class of molecules based on the 1H,7H-pyrazolo[1,2-a]pyrazole-1,7-dione scaffold, were first introduced by E. M. Kosower in 1978. In this study, we report the topochemical cycloaddition of diethyl 2,6-dichloro-1,7-dioxo-1H,7H-pyrazolo[1,2-a]pyrazole-3,5-dicarboxylate (Cl2B), initiated by visible light. Crystal structure analysis confirmed that the reactive double bonds are parallel and coplanar, in line with the Schmidt criteria for topochemical cycloaddition. Additionally, two other bimane derivatives with different substitution patterns were synthesized and investigated. Our findings suggest that functionalizing bimanes to redshift their absorption maxima into the visible-light spectrum provides a promising strategy for synthesizing substituted cyclobutanes without the need for ultraviolet irradiation.https://doi.org/10.3762/bjoc.21.37bimane[2 + 2] cycloadditionfluorescencetopochemical polymerizationx-ray crystallography |
| spellingShingle | Metodej Dvoracek Brendan Twamley Mathias O. Senge Mikhail A. Filatov Unprecedented visible light-initiated topochemical [2 + 2] cycloaddition in a functionalized bimane dye Beilstein Journal of Organic Chemistry bimane [2 + 2] cycloaddition fluorescence topochemical polymerization x-ray crystallography |
| title | Unprecedented visible light-initiated topochemical [2 + 2] cycloaddition in a functionalized bimane dye |
| title_full | Unprecedented visible light-initiated topochemical [2 + 2] cycloaddition in a functionalized bimane dye |
| title_fullStr | Unprecedented visible light-initiated topochemical [2 + 2] cycloaddition in a functionalized bimane dye |
| title_full_unstemmed | Unprecedented visible light-initiated topochemical [2 + 2] cycloaddition in a functionalized bimane dye |
| title_short | Unprecedented visible light-initiated topochemical [2 + 2] cycloaddition in a functionalized bimane dye |
| title_sort | unprecedented visible light initiated topochemical 2 2 cycloaddition in a functionalized bimane dye |
| topic | bimane [2 + 2] cycloaddition fluorescence topochemical polymerization x-ray crystallography |
| url | https://doi.org/10.3762/bjoc.21.37 |
| work_keys_str_mv | AT metodejdvoracek unprecedentedvisiblelightinitiatedtopochemical22cycloadditioninafunctionalizedbimanedye AT brendantwamley unprecedentedvisiblelightinitiatedtopochemical22cycloadditioninafunctionalizedbimanedye AT mathiasosenge unprecedentedvisiblelightinitiatedtopochemical22cycloadditioninafunctionalizedbimanedye AT mikhailafilatov unprecedentedvisiblelightinitiatedtopochemical22cycloadditioninafunctionalizedbimanedye |