Related Experiment Video
Updated: May 10, 2025

Functionalized Spirocyclic Heterocycle Synthesis and Cytotoxicity Assay
Published on: February 9, 2021
Multi-Auto-Tandem Reaction to Access Site-Specific Functionalized Tricyclic Furo[3,2-c]coumarins and
Xiang Liu1, Hexiang Wang1, Dongrong Lin1
1School of Chemistry and Chemical Engineering, Guangdong Pharmaceutical University, Zhongshan 528458, P. R. China.
Abstract:
A three-component multi-auto-tandem reaction for the construction of site-specific tricyclic furo[3,2-c]coumarins via the formation of C-C, C-O, and C-S bonds in one step from 4-hydroxycoumarins/4-hydroxy-2-pyrones, ynals, and sodium sulfinates is reported. This cascade reaction efficiently produces a variety of rare C-2-functionalized furo[3,2-c]coumarins in moderate to good yields under straightforward reaction conditions. Furthermore, this protocol can be extended to a three-component coupling involving 2-hydroxy-1,4-naphthoquinone, ynals, and sodium sulfinates, yielding tricyclic naphtho[2,3-b]furan-4,9-dione derivatives. Notably, the carbonyl group and the α-position of ynals act as C-2 synthons in the specific multi-auto-tandem reaction, enabling the two aforementioned types of multicomponent transformations.
Related Concept Videos
Cycloaddition Reactions: Overview
Cycloaddition Reactions: MO Requirements for Thermal Activation
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Cycloaddition Reactions: MO Requirements for Photochemical Activation
Woodward–Hoffmann Selection Rules and Microscopic Reversibility
Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...

