52124-00-2Relevant articles and documents
Multicomponent Synthesis of Structurally Diverse Imidazoles Featuring Azirines, Amines and Aldehydes
Rossa, Thaís A.,Fantinel, Mariane,Bortoluzzi, Adailton J.,Sá, Marcus M.
supporting information, p. 4171 - 4177 (2018/08/21)
A novel and efficient method for the synthesis of structurally diverse imidazoles through a multicomponent reaction involving an azirine, an amine, and an aldehyde is described. The method is simple and environmentally benign, producing multifunctionalized imidazoles in moderate-to-good yields and in a regioselective manner, which was demonstrated by NMR experiments and X-ray analysis. A mechanism is proposed in which the amine participates not only as a reactant, but also as a nucleophilic reaction promoter.
[3 + 2]-Cycloadditions of nitrile ylides after photoactivion of vinyl azides under flow conditions
Cludius-Brandt, Stephan,Kupracz, Lukas,Kirschning, Andreas
supporting information, p. 1745 - 1750 (2013/10/22)
The photodenitrogenation of vinyl azides to 2H-azirines by using a photoflow reactor is reported and compared with thermal formation of 2H-azirines. Photochemically, the ring of the 2H-azirines was opened to yield the nitrile ylides, which underwent a [3 + 2]-cycloaddition with 1,3-dipolarophiles. When diisopropyl azodicarboxylate serves as the dipolarophile, 1,3,4-triazoles become directly accessible starting from the corresponding vinyl azide.