1361979-13-6Relevant academic research and scientific papers
Geminal Diazides Derived from 1,3-Dicarbonyls: A Protocol for Synthesis
Erhardt, Hellmuth,H?ring, Andreas P.,Kotthaus, Andreas,Roggel, Markus,Tong, My Linh,Biallas, Phillip,Jübermann, Martin,Mohr, Fabian,Kirsch, Stefan F.
, p. 12460 - 12469 (2015)
Geminal diazides constitute a rare class of compounds where only a limited number of methods are available for their synthesis. We present the reaction of 1,3-dicarbonyl compounds (as exemplified by malonates, 3-oxoesters, and 1,3-diketones) with molecular iodine and sodium azide in aqueous DMSO providing a general access to geminal diazides. A broad range of geminal diazides with various structural motifs including sterically demanding substituents and ordinary functional groups were synthesized, and it was shown that the diazidation of 1,3-dicarbonyls can be selectively achieved even in the presence of other 1,3-dicarbonyls with substituents at 2-position. Additionally, several diazides were studied regarding their thermal stability.
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
