دورية أكاديمية
Autocatalytic photoinduced oxidative dehydrogenation of pyrido[2,3-d]pyrimidin-7(8H)-ones: synthesis of C5-C6 unsaturated systems with concomitant formation of a long-lived radical
| العنوان: | Autocatalytic photoinduced oxidative dehydrogenation of pyrido[2,3-d]pyrimidin-7(8H)-ones: synthesis of C5-C6 unsaturated systems with concomitant formation of a long-lived radical |
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| المؤلفون: | Rocafiguera, Claudi de, Lloveras, Vega, Vidal Gancedo, José, Teixidó, Jordi, Estrada Tejedor, Roger, Borrell, José I., Puig de la Bellacasa, Raimon |
| المساهمون: | Ministerio de Ciencia, Innovación y Universidades (España), Agencia Estatal de Investigación (España), Rocafiguera, Claudi de, Lloveras, Vega, Vidal Gancedo, José, Teixidó, Jordi, Borrell, José I., Puig de la Bellacasa, Raimon |
| بيانات النشر: | Royal Society of Chemistry (UK) |
| سنة النشر: | 2023 |
| المجموعة: | Digital.CSIC (Consejo Superior de Investigaciones Científicas / Spanish National Research Council) |
| الوصف: | 5,6-Dihydropyrido[2,3-d]pyrimidin-7(8H)-ones are readily accessed by a variety of methods and are a good scaffold for the development of biologically active compounds. However, they are very reluctant to dehydrogenate to give C5-C6 unsaturated compounds, usually with higher activity. A serendipitous discovery has allowed us to develop an autocatalytic photochemical dehydrogenation process by irradiating at 450 or 365 nm in DMSO, in the presence of air, and at room temperature the corresponding 5,6-dihydro derivative (with a variety of substituents at C2, C4, C5, C6, and N8) without adding any external photosensitizer. A complete study including reactions in DMSO-d6 followed by NMR spectroscopy, EPR experiments, the use of radical quenchers, spin-trapping techniques, and reaction with methyl viologen, complemented with ab initio calculations has allowed us to propose a mechanistic rationalization for such a process. ; This research was funded by Ministerio de Ciencia, Innovación y Universidades, Proyectos de I + D + I “Retos Investigación” del Programa Estatal de I + D + I orientada a los Retos de la Sociedad, grant number RTI2018-096455-B-I00. We thank Dr Alexandr Shafir of the Institute of Advanced Chemistry of Catalonia (IQAC-CSIC) and Dr Ana Belén Cuenca of Institut Químic de Sarrià, Universitat Ramon Llull for giving us the possibility of carrying out the first experiment using Penn PhD Photoreactor M2. We thank one of the referees for very interesting and fruitful suggestions and discussion about the mechanistic proposal. ; With funding from the Spanish government through the ‘Severo Ochoa Centre of Excellence’ accreditation (CEX2019-000917-S). ; Peer reviewed |
| نوع الوثيقة: | article in journal/newspaper |
| اللغة: | English |
| تدمد: | 2052-4110 |
| العلاقة: | #PLACEHOLDER_PARENT_METADATA_VALUE#; info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/RTI2018-096455-B-I00/ES/INHIBIDORES DE TIROSINA QUINASAS DUALES EN CANCER DE PANCREAS: CRIBADO VIRTUAL, SINTESIS, EVALUACION BIOLOGICA IN VITRO (2D Y 3D) E IN VIVO/; info:eu-repo/grantAgreement/AEI/Plan Estatal de investigación Científica y Técnica y de Innovación 2017-2020/CEX2019-000917-S; Organic Chemistry Frontiers; Publisher's version; http://doi.org/10.1039/d3qo01358hTest; Sí; Organic Chemistry Frontiers 11(1): 27-36 (2024); http://hdl.handle.net/10261/341682Test; http://dx.doi.org/10.13039/501100011033Test; 2-s2.0-85176223351; https://api.elsevier.com/content/abstract/scopus_id/85176223351Test |
| DOI: | 10.1039/d3qo01358h |
| DOI: | 10.13039/501100011033 |
| الإتاحة: | https://doi.org/10.1039/d3qo01358h10.13039/501100011033Test http://hdl.handle.net/10261/341682Test https://api.elsevier.com/content/abstract/scopus_id/85176223351Test |
| حقوق: | open |
| رقم الانضمام: | edsbas.3A8A9843 |
| قاعدة البيانات: | BASE |
Full Text Finder | تدمد: | 20524110 |
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| DOI: | 10.1039/d3qo01358h |