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Updated: Oct 7, 2025

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
A Diazo-Hooker Reaction, Inspired by the Biosynthesis of Azamerone
Oussama Yahiaoui1, Lauren A M Murray1, Fengyue Zhao2
1Department of Chemistry, University of Adelaide, Adelaide, SA 5005, Australia.
Abstract:
Motivated by the biosynthesis of azamerone, we report the first example of a diazo-Hooker reaction, which involves the formation of a phthalazine ring system by the oxidative rearrangement of a diazoketone. Computational studies indicate that the diazo-Hooker reaction proceeds via an 8π-electrocyclization followed by ring contraction and aromatization. The biosynthetic origin of the diazoketone functional group was also chemically mimicked using a related natural product, naphterpin, as a model system.
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