A highly
efficient rongalite-mediated three-component radical annulation
reaction to furnish fully substituted pyrazoles from aryldiazonium
salts and α,β-unsaturated aldehydes or ketones under metal-
and oxidant-free conditions at room temperature has been developed.
In this transformation, aryldiazonium salts served as the precursor
of both the aryl and aryl hydrazine units. Mechanistic investigations
indicated that rongalite could act as a radical initiator and reducing
reagent simultaneously in the reaction.
An efficient I2–DMSO reagent system-mediated multicomponent reaction strategy for the synthesis of C3-sulfenylated chromones from o-hydroxyaryl methyl ketones, rongalite, and dimethyl sulfoxide has been developed.
Rongalite
has been used in several challenging synthetic transformations
with operationally simple and effective protocols. However, the employment
of multiple characteristics of rongalite in synthetic chemistry is
comparatively little known. Herein we report a separate-embedding
type sulfonylmethylation of sulfoxonium ylides in which rongalite
concurrently acted as a sulfone source, C1 synthon, radical initiator,
and potential reducing reagent for the first time. Notably, this facile
and easy-handling reaction does not require a catalyst or prefunctionalized
sulfonylmethylation reagents.
The one-pot total
synthesis of evodiamine and its analogues is
achieved using a three-component reaction. Through continuous biscyclization,
various readily available substrates with good functional group tolerance
were easily incorporated into biologically active quinazolinocarboline
backbones. The use of triethoxymethane as a cosolvent was crucial
for this quick and straightforward transformation.
A novel copper-catalyzed sulfur dioxide anion incorporation cascade for the synthesis of 1-thiaflavanone sulfones has been disclosed using rongalite as an economic and safe sulfone source. A series of 1-thiaflavanone...
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