77420-97-4Relevant academic research and scientific papers
Lewis acid-catalyzed generation of C-C and C-N bonds on π-deficient heterocyclic substrates
Staderini, Matteo,Bolognesi, Maria Laura,Menndez, J. Carlos
supporting information, p. 185 - 195 (2015/01/30)
Focused microwave irradiation of a series of halogenated nitrogen heterocycles and different kinds of nucleophiles in the presence of a catalytic amount of indium trichloride leads to the efficient and completely regioselective generation of aromatic C-C and C-N bonds. The method is simple, rapid, general and inexpensive, and can be performed without the use of dried solvents. Most of the synthetized compounds are new and in many cases the work-up required only filtration. Furthermore, this is the first example of the use of a Lewis acid as a catalyst for heteroarylation, vinylation and amination reactions on π-deficient heterocyclic substrates.
Solvent- and chromatography-free amination of π-deficient nitrogen heterocycles under microwave irradiation. A fast, efficient and green route to 9-aminoacridines, 4-aminoquinolines and 4-aminoquinazolines and its application to the synthesis of the drugs amsacrine and bistacrine
Staderini, Matteo,Cabezas, Nieves,Bolognesi, Maria Laura,Menéndez, J. Carlos
, p. 1024 - 1030 (2013/02/23)
Focused microwave irradiation of equimolecular mixtures of 9-chloroacridines, 4-chloroquinolines and 4-chloroquinazolines with amines in the presence of 2 equiv of phenol allows the general, fast and high-yielding synthesis of aminated heterocycles, with a very broad scope in terms of amine structure (aromatic, linear primary aliphatic, α-branched primary aliphatic, secondary aliphatic and diamines). Workup consisted of a simple washing with water and purification could be achieved by crystallization, avoiding the use of organic solvents in extraction and chromatographic purification steps. This protocol provides a solution to the long-standing synthetic problem of achieving a practical and efficient method for the amination of π-deficient nitrogen heterocycles for medicinal chemistry applications.
