Palladium-Catalyzed [5 + 2] Rollover Annulation of 1-Benzylpyrazoles with Alkynes: A Direct Entry to Tricyclic 2-Benzazepines
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ISSN: 1523-7060
E-ISSN: 1523-7052
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American Chemical Society
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Abstract
The first Pd-catalyzed [5 + 2] rollover annulation of 1-benzylpyrazoles with alkynes to assemble 10H-benzo[e]pyrazolo[1,5-a]azepines (tricyclic 2-benzazepines) has been developed. The rollover annulation implies a twofold C–H activation of aryl and heteroaryl Csp2–H bonds (C–H/C–H) of 1-benzylpyrazoles (five-atom partners) and alkynes to give the [5 + 2] annulated compounds.
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Suárez-Lustres, A., Martínez-Yáñez, N., Velasco-Rubio, A., Varela, J. A., Saá, C. (2023). Palladium-Catalyzed [5 + 2] Rollover Annulation of 1-Benzylpyrazoles with Alkynes: A Direct Entry to Tricyclic 2-Benzazepines. Org. Lett., 25, 5, 794-799
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https://doi.org/10.1021/acs.orglett.2c04300Sponsors
We acknowledge financial support from MICINN (Project PID2020-118048GB-I00 and ORFEO−CINQA Network
RED2018-102387-T), the Xunta de Galicia (Project ED431C 2022/27 and Centro Singular de Investigación de
Galicia Accreditation 2019−2022, ED431G 2019/03), and the European Union (European Regional Development Fund). A.S.-L. thanks MICINN for a predoctoral contract.
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© 2023 American Chemical Society. This is an open access article under the CC Attribution 4.0 International (CC BY 4.0) license (http://creativecommons.org/licenses/by/4.0/)