Site-Selective Conversion of Azido Groups at Carbonyl alpha-Positions to Diazo Groups in Diazido and Triazido Compounds

摘要

This paper reports on the selective conversion of alkyl azido groups at the carbonyl alpha-position to diazo compounds. Through beta-elimination of dinitrogen, followed by hydrazone formation/decomposition, alpha-azidocarbonyl moieties were transformed into alpha-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.