Title

The Cascade Reactions of Indigo with Propargyl Substrates for Heterocyclic and Photophysical Diversity

Publication Name

Chemistry - A European Journal

Abstract

The synthesis of structurally diverse heterocycles for chemical space exploration was achieved via the cascade reactions of indigo with propargylic electrophiles. New pyrazinodiindolodione, naphthyridinedione, azepinodiindolone, oxazinoindolone and pyrrolodione products were prepared in one pot reactions by varying the leaving group (-Cl, -Br, -OMs, -OTs) or propargyl terminal functionality (-H, -Me, -Ph, -Ar). Mechanistic and density functional theory studies revealed that the unsaturated propargyl moiety can behave as an electrophile when aromatic terminal substitutions are made, and therefore competes with leaving group substitution for new outcomes. Selected products from the cascade reactions were investigated for their absorption and fluorescence properties, including transient absorption spectroscopy. This revealed polarity dependent excited state relaxation pathways, fluorescence, and triplet formation, thus highlighting these reactions as a means to access diverse functional materials rapidly.

Open Access Status

This publication is not available as open access

Volume

27

Issue

11

First Page

3708

Last Page

3721

Funding Sponsor

Friedrich-Alexander-Universität Erlangen-Nürnberg

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Link to publisher version (DOI)

http://dx.doi.org/10.1002/chem.202003662