3818-16-4Relevant academic research and scientific papers
Sulfonium ion-promoted traceless Schmidt reaction of alkyl azides
Ardiansah, Bayu,Kakiuchi, Kiyomi,Morimoto, Tsumoru,Tanimoto, Hiroki,Tomohiro, Takenori
supporting information, p. 8738 - 8741 (2021/09/08)
Schmidt reaction by sulfonium ions is described. General primary, secondary, and tertiary alkyl azides were converted to the corresponding carbonyl or imine compounds without any trace of the activators. This bond scission reaction through 1,2-migration of C-H and C-C bonds was accessible to the one-pot substitution reaction.
Photoinduced α-Cleavage of 2-Azido-2-phenyl-1,3-indandione at Cryogenic Temperatures
Abe, Manabu,Banerjee, Upasana,Gudmundsdottir, Anna D.,Karney, William L.,Krause, Jeanette A.,Sarkar, Sujan K.
supporting information, p. 7885 - 7890 (2020/11/02)
To expand the utility of α-cleavage at cryogenic temperatures, we investigated the photoreactivity of 2-azido-2-phenyl-1,3-indandione (1). EPR spectroscopy revealed that irradiating 1 in 2-methyltetrahydrofuran (mTHF) matrices forms alkylnitrene 32, which has zero-field splitting parameters (D/hc = 1.5837 cm-1 E/hc = 0.0039 cm-1) typical of an alkylnitrene. IR spectroscopy demonstrated that irradiating 1 in argon matrices results in the concurrent formation of 32, imine 3, benzocyclobutenedione 4, and benzonitrile 5.
Ring Expansion of 2-Azido-2-phenyl-indan-1,3-dione for the Generation of Heterocyclic Scaffolds
Mittendorf, Fabia,Mohr, Fabian,Kirsch, Stefan F.
, p. 12760 - 12769 (2020/10/09)
A novel ring expansion based on the readily available 2-azido-2-phenyl-indan-1,3-dione is described. Treatment with primary amines and cesium carbonate in a two-step sequence gives rise to 3-amino-2,3-dihydroisoquinoline-1,4-diones with an unprecedented substitution pattern. The corresponding conversion using amino acid methyl esters leads directly to a novel tricyclic 1,10a-dihydroimidazo-isoquinoline-2,5,10-trione scaffold, a structure that has never been reported before, to the best of our knowledge.
