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Updated: Mar 3, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
C-H Functionalization of Azines
Kei Murakami1, Shuya Yamada1, Takeshi Kaneda1
1Institute of Transformative Bio-Molecules (WPI-ITbM) and Graduate School of Science, and ‡JST-ERATO, Itami Molecular Nanocarbon Project, Nagoya University , Chikusa, Nagoya 464-8602, Japan.
Abstract:
Azines, which are six-membered aromatic compounds containing one or more nitrogen atoms, serve as ubiquitous structural cores of aromatic species with important applications in biological and materials sciences. Among a variety of synthetic approaches toward azines, C-H functionalization represents the most rapid and atom-economical transformation, and it is advantageous for the late-stage functionalization of azine-containing functional molecules. Since azines have several C-H bonds with different reactivities, the development of new reactions that allow for the functionalization of azines in a regioselective fashion has comprised a central issue. This review describes recent advances in the C-H functionalization of azines categorized as follows: (1) SNAr reactions, (2) radical reactions, (3) deprotonation/functionalization, and (4) metal-catalyzed reactions.
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