Modular Route to Azaindanes

Abstract : A convergent radical based route to azaindanes is described, relying on the degenerative addition transfer of various substituted S-(pyridylmethyl)-O-ethyl dithiocarbonates (xanthates) to functional alkenes followed by radical cyclization onto the pyridine ring activated by protonation with trifluoroacetic acid. In one case, a richly decorated cyclohepta[b]pyridine could be assembled swiftly by allowing the first adduct to N-phenylmaleimide to undergo addition to N-allylphthalimide prior to cyclization.
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Submitted on : Wednesday, April 10, 2019 - 11:09:36 AM
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Qi Huang, Samir Zard. Modular Route to Azaindanes. Organic Letters, American Chemical Society, 2017, 19 (14), pp.3895-3898. ⟨https://pubs.acs.org/doi/10.1021/acs.orglett.7b01772⟩. ⟨10.1021/acs.orglett.7b01772⟩. ⟨hal-02095075⟩

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