In:
Organic Chemistry Frontiers, Royal Society of Chemistry (RSC), Vol. 10, No. 16 ( 2023), p. 4122-4130
Abstract:
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.
Type of Medium:
Online Resource
ISSN:
2052-4129
Language:
English
Publisher:
Royal Society of Chemistry (RSC)
Publication Date:
2023
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