jo8b02074_si_003.cif (1.63 MB)
Download fileSite-Selective Conversion of Azido Groups at Carbonyl α‑Positions to Diazo Groups in Diazido and Triazido Compounds
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posted on 2018-09-26, 21:29 authored by Taiki Yokoi, Hiroki Tanimoto, Tomomi Ueda, Tsumoru Morimoto, Kiyomi KakiuchiThis paper reports on the selective
conversion of alkyl azido groups
at the carbonyl α-position to diazo compounds. Through β-elimination
of dinitrogen, followed by hydrazone formation/decomposition, α-azidocarbonyl
moieties were transformed into α-diazo carbonyl groups in one
step. As these reaction conditions do not involve aryl or general
alkyl azides, site-selective conversions of di- and triazides were
achieved. Through this method, the successive site-selective conjugation
of the triazido molecule with three different components is demonstrated.