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Updated: Jun 28, 2025

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Sequential Dearomatization/Rearrangement of Quinazoline-Derived Azomethine Imines for the Synthesis of Nitrogen-Rich
Yu-Jiao Wang1,2, Chun-Guang Yang2, Shuang Wang2
1School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, Shandong, China.
Abstract:
A sequential dearomatization/rearrangement reaction between quinazoline-derived azomethine imines and crotonate sulfonium salts has been developed to provide a series of three-dimensional cage-like molecules. The reaction involves two dearomatizations, two cyclizations, and two C-C bond and three C-N bond formations in one step. The new transformation has a broad substrate scope, does not require any added reagents, and proceeds under room temperature in a short time. A mechanistic rationale for the sequential dearomatization/rearrangement is also presented. Furthermore, the synthetic compounds are evaluated for their glucose control effect. Compounds 3aa and 3aj were found to be hyperglycemic, which might be lead compounds for treating hypoglycemia.
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