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Updated: Jun 6, 2025

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
[1,5]-Oxy/Thio/Azole Sigmatropic Rearrangement versus Indolyl-Spirocyclization: Tandem Reactions of 2-Azidobenzoate
Shu Chen1, Xin Wang2, Wenhui Yang1
1College of Chemistry, Chemical Engineering and Materials Science, Collaborative Innovation Center of Functionalized Probes for Chemical Imaging in Universities of Shandong, Key Laboratory of Molecular and Nano Probes, Ministry of Education, Shandong Provincial Key Laboratory of Clean Production of Fine Chemicals, Shandong Normal University, Jinan 250014, China.
Abstract:
A general protocol for the synthesis of a variety of functionalized quinazolinones has been developed through a sequential Pd-catalyzed coupling/1,5-alkyloxy/thio/azole shift/6π electrocyclization reaction of isocyanides and 2-carbonylaryl azides. When 3-(2-isocyanoethyl)indoles were utilized, an unusual competitive reaction between [1,5]-shift and indole-spirocyclization was observed, which renders a modular synthesis of quinazolinones and spiroindolenine-3,3'-pyrrolo[2,1-b]quinazolinones in a highly chemoselective manner.
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