Cascade Reactions of Indigo with an Allenylic Reactant

Cascade Reactions of Indigo with an Allenylic Reactant

The base-enabled reaction of buta-2,3-dien-1-yl methanesulfonate with the readily available and cheap dye indigo resulted in the convenient one-pot synthesis of benzoindolonaphthyridinedione and benzoazepinopyridoindolediones, with the latter representing two novel heterocyclic scaffolds. Despite th...

Full description

Saved in:
Bibliographic Details
Main Authors: Dyah U. C. Rahayu, Christopher Richardson, John B. Bremner, Paul A. Keller
Format: Article
Language:English
Published: MDPI AG 2025-07-01
Series:Molecules
Subjects:
indigo
cascade reaction
allenylic electrophile
benzoindolonaphthyridinedione
benzoazepinopyridoindolediones
Online Access:https://www.mdpi.com/1420-3049/30/14/2899
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The base-enabled reaction of buta-2,3-dien-1-yl methanesulfonate with the readily available and cheap dye indigo resulted in the convenient one-pot synthesis of benzoindolonaphthyridinedione and benzoazepinopyridoindolediones, with the latter representing two novel heterocyclic scaffolds. Despite the low yields, the allenylic alkylation of indigo significantly contributes to the new chemistry of this compound, providing new mechanistic insights and reactivity boundaries.
ISSN:1420-3049

Similar Items