Issue 21, 2025

Synthesis of 6-arylpyrimido[4,5-e]indolizine-2,4(1H,3H)-diones through InCl3-catalyzed cycloisomerization

Abstract

We report the synthesis of hitherto unknown pyrimido[4,5-e]indolizine-2,4(1H,3H)-diones (indolizinouracils) and related polycondensed uracils. The synthetic strategy is based on a chemoselective C–N coupling through an addition–elimination reaction of N,N-dimethyl-5-bromo-6-chlorouracil with N-heterocycles, followed by Sonogashira cross-coupling reaction with alkynes and InCl3-catalysed cycloisomerisation. The methodology allows for the employment of pyrrole and indole as N-heterocyclic building blocks and tolerates various functional groups. The impact of the substitution pattern on the photophysical properties was studied by steady-state UV-Vis and fluorescence spectroscopy, providing new insights into the potential applications of uracil-based polycondensed heterocycles.

Graphical abstract: Synthesis of 6-arylpyrimido[4,5-e]indolizine-2,4(1H,3H)-diones through InCl3-catalyzed cycloisomerization

Supplementary files

Article information

Article type
Paper
Submitted
11 Maw 2025
Accepted
24 Ebr 2025
First published
07 Mai 2025
This article is Open Access
Creative Commons BY license

Org. Biomol. Chem., 2025,23, 5215-5223

Synthesis of 6-arylpyrimido[4,5-e]indolizine-2,4(1H,3H)-diones through InCl3-catalyzed cycloisomerization

R. M. Figueira de Abreu, A. Villinger, P. Ehlers and P. Langer, Org. Biomol. Chem., 2025, 23, 5215 DOI: 10.1039/D5OB00436E

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