243-47-0Relevant academic research and scientific papers
Iodothiophenes and Related Compounds as Coupling Partners in Copper-Mediated N-Arylation of Anilines
Bouarfa, Salima,Bentabed-Ababsa, Ghenia,Erb, William,Picot, Laurent,Thiéry, Valérie,Roisnel, Thierry,Dorcet, Vincent,Mongin, Florence
, p. 1271 - 1284 (2020/11/09)
N-Arylation of various 2-acylated anilines with different electron-rich heteroaryl iodides (2- A nd 3-iodothiophenes, 2- A nd 3-iodobenzothiophenes?-, 2-iodobenzofuran) was achieved by using activated copper and potassium carbonate in dibutyl ether at reflux. The reactivity of the different heteroaryl iodides and anilines employed was discussed and rationalized on the basis of their electronic features. Subsequent cyclization by aromatic electrophilic substitution easily took place in the case of C2-free (benzo)thienyl or C3-free (benzo)furyl derivatives?-, affording original tri- A nd tetracycles. The antiproliferative activity of most of them was evaluated in A2058 melanoma cells and revealed four chlorinated tetracycles as effective growth inhibitors.
Synthesis of Indolo-and Benzothieno[2,3-b]quinolines by a Cascade Cyclization of o-Alkynylisocyanobenzene Derivatives
Khaikate, Onnicha,Inthalaeng, Natthamon,Meesin, Jatuporn,Kantarod, Kritchasorn,Pohmakotr, Manat,Reutrakul, Vichai,Soorukram, Darunee,Leowanawat, Pawaret,Kuhakarn, Chutima
, (2019/11/29)
A new synthetic approach for the synthesis of indolo[2,3-b]quinolines and benzothieno[2,3-b]quinolines has been developed by employing the freshly prepared o-alkynylisocyanobenzenes derived from o-alkynylformamide derivatives as substrates. The synthetic transformations involved chloride-ion-triggered 6-endo cyclization of o-alkynylisocyanobenzenes to generate 2-chloroquinolines in situ, which further cyclized intramolecularly with nitrogen or sulfur atom via a cascade process to provide the corresponding indolo[2,3-b]quinolines and benzothieno[2,3-b]quinolines, respectively, in moderate to excellent yields.
Cobalt-Catalyzed Electrophilic Aminations with Anthranils: An Expedient Route to Condensed Quinolines
Li, Jie,Tan, Eric,Keller, Niklas,Chen, Yi-Hung,Zehetmaier, Peter M.,Jakowetz, Andreas C.,Bein, Thomas,Knochel, Paul
supporting information, p. 98 - 103 (2019/01/08)
The reaction of various organozinc pivalates with anthranils provides anilines derivatives, which cyclize under acidic conditions providing condensed quinolines. Using alkenylzinc pivalates, electron-rich arylzinc pivalates or heterocyclic zinc pivalates produces directly the condensed quinolines of which several structures belong to new heterocyclic scaffolds. These N-heterocycles are of particular interest for organic light emitting diodes with their high photoluminescence quantum yields and long exciton lifetimes as well as for hole-transporting materials in methylammonium lead iodide perovskites solar cells due to an optimal band alignment for holes and a large bandgap.
