Title:
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Silver-Mediated Cascade Synthesis of Functionalized 1,4-dihydro-2H-Benzo-1,3-Oxazin-2-Ones from Carbon Dioxide
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Author:
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Li, Xuetong; Benet-Buchholz, Jordi; Escudero-Adán, Eduardo C.; Kleij, Arjan W.
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Abstract:
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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. |
Publication date:
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2023-01-13 |
Subject (UDC):
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00 - Ciència i coneixement. Investigació. Cultura. Humanitats |
Subject(s):
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Química |
Rights:
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Creative Commons Attribution-NonCommercial-NoDerivs License |
Pages:
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9 p. |
Document type:
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Article Article - Accepted version |
DOI:
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10.1002/anie.202217803
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Published by:
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Wiley-VCH
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