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Updated: Jul 12, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Synthesis of 9-(Piperidin-3-yl)purine Derivatives via [4 + 2] Cycloaddition of Aza-π-allylpalladium 1,4-Dipole
Rong-Nan Cui1, Lu-Xin Li1, Dong-Chao Wang1
1State Key Laboratory of Antiviral Drugs, Pingyuan Laboratory, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, China.
Abstract:
The synthesis of 9-(piperidin-3-yl)purines is reported via a [4 + 2] cycloaddition reaction of 2-(purin-9-yl)propenone derivatives with aza-π-allylpalladium 1,4-dipole derived in situ from p-toluenesulfonamide-substituted acyclic allylic carbonate. The method features a broad substrate scope, and synthetic transformations of the products further demonstrate their utility. The enantioselective cycloaddition was also demonstrated with up to 60% ee. Preliminary in vitro tests showed that compound 3f exhibits potent antitumor activity (IC50 = 2.02 μM for HCT116; IC50 = 0.73 μM for HeLa), indicating these derivatives hold strong potential for antitumor drugs.
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