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Updated: Jul 1, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Azirine-2-carbonyl Azides as C3-Synthons in the Reaction with Amidines toward 5-Aminopyrimidin-4(3H)-ones
Daniil D Lyakhov1, Timur O Zanakhov1, Ekaterina E Galenko1
1St. Petersburg State University, Institute of Chemistry, 7/9 Universitetskaya nab., St. Petersburg 199034, Russia.
Abstract:
The azide group in azirine-2-carbonyl azides provides a unique electrophilic balance of the reaction sites, allowing these compounds to be used as all-carbon C3 synthons in the synthesis of N',N'-unsubstituted 5-aminopyrimidin-4-ones via a (3 + 3) cyclocondensation reaction with amidines. Strongly basic conditions alter the reactivity of the key intermediate 2,4,7-triazabicyclo[4.1.0]hept-2-en-5-one, resulting in a formal (4 + 3) cyclocondensation reaction to afford 3,7-dihydro-6H-1,3,5-triazepin-6-ones as the sole products.
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