1361979-10-3Relevant academic research and scientific papers
An efficient tertiary azidation of 1,3-dicarbonyl compounds in water catalyzed by tetrabutylammonium iodide
Dhineshkumar, Jayaraman,Prabhu, Kandikere Ramaiah
, p. 447 - 452 (2016)
An efficient azidation of 1,3-dicarbonyl compounds led to tertiary azides in the presence of tetrabutylammonium iodide (TBAI). TBAI is used as a pre-catalyst along with aq. tert-butyl hydroperoxide (TBHP) as an oxidant in aqueous medium. This operationally simple, practical, mild and green method provides an opportunity to synthesize a variety of azidated β-keto esters, amides, and ketones in good yields. 1,3-Dicarbonyl compounds undergo a facile azidation to furnish the corresponding tertiary azides. This method employs tetrabutylammonium iodide (TBAI) as a catalyst, aq. tert-butyl hydroperoxide (TBHP) as an oxidant and TMSN3 as an azide source. This strategy is general and works well for β-keto esters, β-diketones, and β-keto amides and furnish their corresponding tertiary azides in good yields.
Practical azidation of 1,3-dicarbonyls
Harschneck, Tobias,Hummel, Sara,Kirsch, Stefan F.,Klahn, Philipp
, p. 1187 - 1193 (2012/03/11)
An operationally simple, direct azidation of 1,3-dicarbonyl compounds has been developed. The reaction proceeds readily under ambient conditions using sodium azide and an iodine-based oxidant such as I2 or 2-iodoxybenzoic acid (IBX)-SO3K/NaI. In particular, the latter method, as a new and well-balanced oxidizing agent, shows excellent functional group tolerance and substrate scope and thus allows access to a variety of tertiary 2-azido and 2,2-bisazido 1,3-dicarbonyl compounds that would be more difficult to access by using traditional methods. Because the azide-containing products easily undergo 1,3-dipolar cycloaddition with alkynes, our report represents a novel route to analogues of sensitive complex molecules. Click into place! An operationally simple, direct azidation of 1,3-dicarbonyl compounds has been developed (see scheme). The reaction proceeds readily under ambient conditions using sodium azide and an iodine-based oxidant, such as I2 or 2-iodoxybenzoic acid (IBX)-SO3K/NaI. The oxidative methods show excellent functional-group tolerance and substrate scope and thus allow access to a variety of tertiary 2-azido and 2,2-bisazido 1,3-dicarbonyl compounds. Copyright
