74530-30-6Relevant articles and documents
Insertion of Isocyanides into N?Si Bonds: Multicomponent Reactions with Azines Leading to Potent Antiparasitic Compounds
Kishore, Kranti G.,Ghashghaei, Ouldouz,Estarellas, Carolina,Mestre, M. Mar,Monturiol, Cristina,Kielland, Nicola,Kelly, John M.,Francisco, Amanda Fortes,Jayawardhana, Shiromani,Mu?oz-Torrero, Diego,Pérez, Belén,Luque, F. Javier,Gámez-Monta?o, Rocío,Lavilla, Rodolfo
supporting information, p. 8994 - 8998 (2016/07/26)
Trimethylsilyl chloride is an efficient activating agent for azines in isocyanide-based reactions, which then proceed through a key insertion of the isocyanide into a N?Si bond. The reaction is initiated by N activation of the azine, followed by nucleophilic attack of an isocyanide in a Reissert-type process. Finally, a second equivalent of the same or a different isocyanide inserts into the N?Si bond leading to the final adduct. The use of distinct nucleophiles leads to a variety of α-substituted dihydroazines after a selective cascade process. Based on computational studies, a mechanistic hypothesis for the course of these reactions was proposed. The resulting products exhibit significant activity against Trypanosoma brucei and T. cruzi, featuring favorable drug-like properties and safety profiles.
Amidines. Part 20. Rate of Reaction of N,N-Dialkylformamide Acetals with Substituted Anilines
Osek, Jerzy,Oszczapowicz, Janusz,Drzewinski, Witold
, p. 1961 - 1964 (2007/10/02)
Rate of reaction of seven N,N-dialkylformamide acetals R2N-CH(OR2)2 with a series of anilines substituted on the phenyl ring have been measured in benzene, methanol, chloroform, and tetrahydrofuran by use of a g.l.c. method.In each case studied reaction is irreversible and obeys a second-order kinetic equation.Reaction rates correlate with Hammett ? constants for substituents on the phenyl ring of the aniline molecule.On the basis of the kinetic data, the mechanism of reaction is discussed.
