A Rh(III)-catalyzed enaminone-directed alkenyl C-H coupling with alkynes for the synthesis of salicylaldehyde derivatives is reported. This represents a unique example of benzene ring framework formation through a transition-metal-catalyzed, directed C-H activation strategy. The two incorporated reactive functionalities, aldehyde and hydroxy groups, provide convenient synthetic handles for further structural elaboration.
We
report herein the first use of N-chloroimines as
effective synthons for directed C–H functionalization. Rh(III)-catalyzed
coupling of N-chloroimines with α-diazo-α-phosphonoacetates
allows for efficient dechlorinative/dephosphonative access to 2H-isoindoles. Further deesterification under Ni(II) catalysis
enables the complete elimination of reactivity-assisting groups and
full exposure of reactivity of C3 and N2 ring atoms for attaching
structurally distinct appendages.
Herein
we report a DNA-compatible Biginelli reaction
to construct
isocytosine scaffolds. This reaction utilizes a one-pot reaction
of DNA-conjugated guanidines with aldehydes and methyl cyanoacetates
to give isocytosine derivatives, and the method is well compatible
with different types of substrates. This is the first report on the
synthesis of an isocytosine backbone in the field of DNA-compatible
organic synthesis. The successful development of this reaction can
widen the chemical space of DELs.
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