Highly Diastereoselective Construction of Novel Dispiropyrrolo[2,1-]isoquinoline Derivatives Multicomponent 1,3-dipolar Cycloaddition of Cyclic Diketones-based Tetrahydroisoquinolinium -ylides

Overview

Journal RSC Adv

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2022 May 13

PMID 35558642

Authors

Sarra Boudriga

Saoussen Haddad

Moheddine Askri

Armand Soldera

Michael Knorr

Carsten Strohmann

Christopher Golz

Affiliations

Soon will be listed here.

Abstract

In the quest for new heterocyclic scaffolds exhibiting potentially biological activities for medicinal chemistry, a multicomponent 1,3-dipolar cycloaddition reaction of tetrahydroisoquinolinium -ylides, generated from cyclic diketones and isoquinoline, and ()-3-arylidene-1-phenyl-pyrrolidine-2,5-diones has been developed. This route provides workable access to dispiropyrrolo[2,1-]isoquinoline-fused pyrrolidine-2,5-diones bearing two adjacent spiro-carbons. An unprecedented regioselectivity was observed in this 1,3-dipolar cycloaddition, leading to the construction of a novel dispirooxindole skeleton. The structure and relative stereochemistry of the spiranic adducts have been confirmed by three X-ray diffraction studies. To reinforce the observed regio- and stereoselectivity of the [3+2] cycloaddition, calculations using the DFT approach at the B3LYP/6-31G(d,p) level were carried out. It was found that this reaction affords the kinetic products.

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