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Two-Step, One-Pot Synthesis of Visible-Light-Responsive 6‑Azopurines

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journal contribution
posted on 2017-09-08, 20:43 authored by Dušan Kolarski, Wiktor Szymanski, Ben L. Feringa
The first general two-step, one-pot synthetic route to 6-azopurines is presented. Microwave-assisted nucleophilic aromatic substitution of protected 6-chloropurines with hydrazines or hydrazides, followed by metal-free oxidation with oxygen, gives 6-azopurines in high to excellent yields. Photophysical studies revealed intensive n−π* absorption band that makes trans-to-cis photoswitching possible using visible light (λ = 530 nm).