American Chemical Society
jo8b02074_si_003.cif (1.63 MB)

Site-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 Kakiuchi
This 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.