2026-04-17T00:40:02Zhttps://recercat.cat/oai/request

oai:recercat.cat:2072/5329302024-12-20T22:50:15Zcom_2072_300912com_2072_4427col_2072_301309

Silver-Mediated Cascade Synthesis of Functionalized 1,4-dihydro-2H-Benzo-1,3-Oxazin-2-Ones from Carbon Dioxide Li, Xuetong Benet-Buchholz, Jordi Escudero-Adán, Eduardo C. Kleij, Arjan W. A conceptually novel catalytic domino approach is presented for the synthesis of highly functional 1,4-dihydro-2H-1,3-benzoxazine-2-one derivatives. Key to the chemoselectivity is a proper design of the precursor to override thermodynamically favored parasitic cyclization processes and empower the formation of the desired product through Thorpe-Ingold effects. The synthetic diversity of these CO2-based heterocycles is further demonstrated, and the isolation of a reaction intermediate supports an unusual ring-expansion sequence from an -alkylidene, five-membered cyclic carbonate to a six-membered cyclic carbamate by N-induced isomerization. 2024-01-13T01:45:05Z 2024-04-23T10:54:01Z 2024-01-13T01:45:05Z 2024-04-23T10:54:01Z 2024-01-13T01:45:05Z 2024-04-23T10:54:01Z 2023-01-13 info:eu-repo/semantics/article info:eu-repo/semantics/acceptedVersion http://hdl.handle.net/2072/532930 https://doi.org/10.1002/anie.202217803 eng Cerca program/Generalitat de Catalunya ICREA MINECO (PID2020-112684GB-100) Ministerio de Ciencia e Innovación (Severo Ochoa Excellence Accreditation 2020–2023 CEX2019-000925-S) Chinese Research Council for a predoctoral fellowship (2019-06870036) info:eu-repo/semantics/openAccess Creative Commons Attribution-NonCommercial-NoDerivs License Wiley-VCH RECERCAT (Dipòsit de la Recerca de Catalunya)