Journal
ORGANIC CHEMISTRY FRONTIERS
Volume 10, Issue 16, Pages 4122-4130Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d3qo00836c
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We report a highly efficient one-pot, four-component reaction mediated by I-2-DMSO to construct a multifunctional fused system. This approach allows for selective formation of aromatics and non-aromatics under temperature control, resulting in planar and non-planar tetracyclic architectures that can be converted using simple methods.
The pyrazolo-azepino-centred polyheterocyclic fused system is a privileged scaffold, but it lacks an effective synthetic approach, with modular synthesis being even more scarce. Accordingly, we herein report a highly efficient I-2-DMSO-mediated one-pot, four-component protocol to construct this fascinating scaffold. This system provides an unprecedented temperature-controlled highly selective formation of aromatics and non-aromatics, affording planar and non-planar tetracyclic architectures that can be interconverted surprisingly by simple methods. Mechanistically, a cooperative aza-[4 + 3] cycloaddition is responsible for the skeleton construction process, while the endogenous oxidant I-2 is responsible for the subsequential aromatization stage.
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