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Updated: Feb 28, 2026

Facile Preparation of 4-Substituted Quinazoline Derivatives

Facile Preparation of 4-Substituted Quinazoline Derivatives

Published on: February 15, 2016

新規のスクアラミド環への分子内マイケル付加を介した高蛍光性キノキサリノ[2,3-b]キノキサリン多環式誘導体の合成

Giacomo Picci¹, Jessica Milia¹, Vito Lippolis¹

¹Department of Chemical and Geological Science, University of Cagliari, S.S. 554 Bivio per Sestu, 09042 Monserrato, CA, Italy.

The Journal of organic chemistry

|February 27, 2026

Abstract:

In the presence of TBAOH, bis-indolylsquaramide (1) converts into the highly emissive, novel bis(3H-pyrrolo[1,2,3-de]quinoxaline) exa-cyclic derivative 2. This compound was fully characterized in solution and the solid state, with emission properties supported by DFT calculations. Derivative 2 exhibits high quantum yield in solution with aggregation-induced quenching, and a large spectral shift between solid state and solution. Reaction conditions were optimized, and a mechanism involving a double intramolecular Michael addition triggered by deprotonation, oxidation and photodecarbonylation was proposed on the basis of DFT calculations and LC-MS measurements. In addition to reporting a novel, highly π-conjugated emissive compound, this manuscript highlights an unprecedented squaramide reactivity under basic conditions, resulting in the first example of intramolecular quinoxaline moiety formation from a squaramide derivative.

キーワード:

スクアラミドキノキサリンマイケル付加蛍光有機合成

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