Photoinduced [4 + 2]-cycloaddition reactions of vinyldiazo compounds for the construction of heterocyclic and bicyclic rings.
| Autor: | Bao M; Department of Chemistry, The University of Texas at San Antonio San Antonio Texas 78249 USA michael.doyle@utsa.edu., Bohórquez ARR; Department of Chemistry, The University of Texas at San Antonio San Antonio Texas 78249 USA michael.doyle@utsa.edu.; Grupo de Investigación en Compuestos Orgánicos de Interés Medicinal (CODEIM), Parque Tecnológico Guatiguará, Universidad Industrial de Santander A. A. 678 Piedecuesta Colombia., Arman H; Department of Chemistry, The University of Texas at San Antonio San Antonio Texas 78249 USA michael.doyle@utsa.edu., Doyle MP; Department of Chemistry, The University of Texas at San Antonio San Antonio Texas 78249 USA michael.doyle@utsa.edu. |
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| Jazyk: | angličtina |
| Zdroj: | Chemical science [Chem Sci] 2024 Jun 28; Vol. 15 (30), pp. 12042-12046. Date of Electronic Publication: 2024 Jun 28 (Print Publication: 2024). |
| DOI: | 10.1039/d4sc03558e |
| Abstrakt: | Highly selective formal [4 + 2]-cycloaddition of vinyldiazoacetates with azoalkenes from α-halohydrazones, as well as with cyclopentadiene and furan, occurs with light irradiation at room temperature, producing highly functionalized heterocyclic and bicyclic compounds in good yields and excellent diastereoseletivity. Under blue light these vinyldiazoacetate reagents selectively form unstable cyclopropenes that undergo intermolecular cycloaddition reactions at a faster rate than their competitive ene dimerization. [4 + 2]-cycloaddition of vinyldiazoacetates with in situ formed azoalkenes produces bicyclo[4.1.0]tetrahydropyridazine derivatives and, together with their cycloaddition using cyclopentadiene and furan that form tricyclic compounds, they occur with high chemoselectivity and diastereocontrol, good functional group tolerance, and excellent scalability. Subsequent transformations portray the synthetic versatility of these structures. Competing Interests: There are no conflicts to declare. (This journal is © The Royal Society of Chemistry.) |
| Databáze: | MEDLINE |
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