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- W2970291149 abstract "Pyrimidines are almost unreactive partners in Diels–Alder cycloadditions with alkenes and alkynes, and only reactions under drastic conditions have previously been reported. We describe how 2-hydrazonylpyrimidines, easily obtained in two steps from commercially available 2-halopyrimidines, can be exceptionally activated by trifluoroacetylation. This allows a Diels–Alder cycloaddition under very mild reaction conditions, leading to a large diversity of aza-indazoles, a ubiquitous scaffold in medicinal chemistry. This reaction is general and scalable and has an excellent functional group tolerance. A straightforward synthesis of a key intermediate of Bayer’s Vericiguat illustrates the potential of this cycloaddition strategy. Quantum mechanical calculations show how the simple N-trifluoroacetylation of 2-hydrazonylpyrimidines distorts the substrate into a transition-state-like geometry that readily undergoes the intramolecular Diels–Alder cycloaddition." @default.
- W2970291149 created "2019-09-05" @default.
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- W2970291149 date "2019-09-02" @default.
- W2970291149 modified "2023-09-25" @default.
- W2970291149 title "Activating Pyrimidines by Pre-distortion for the General Synthesis of 7-Aza-indazoles from 2-Hydrazonylpyrimidines via Intramolecular Diels–Alder Reactions" @default.
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- W2970291149 doi "https://doi.org/10.1021/jacs.9b07037" @default.
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