59236-18-9

Upstream product

• 59236-03-2 3-acetoxy-4-phenyl-2,3-dihydro-furo[2,3-b]quinoline 
• 65418-10-2 4-phenyl-2,3-dihydro-furo[2,3-b]quinoline 
• 54829-48-0 2-iodofuran 
• 2835-77-0 (2-aminophenyl)(phenyl)methanone 
• 59236-33-8 4-phenyl-3-vinyl-1H-quinolin-2-one 

Relevant academic research and scientific papers

Iodothiophenes and Related Compounds as Coupling Partners in Copper-Mediated N-Arylation of Anilines

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.

2-Aminophenones, a common precursor to N-aryl isatins and acridines endowed with bioactivities

Because N-arylation of isatin only worked with iodoferrocene (and in low yield), we employed N-arylation of 2-aminophenones and subsequent oxidative cyclization to access various N-arylated isatins. In the course of this work, we observed that N-arylation using 2-iodofuran, 2-iodobenzofuran and 2-iodobenzothiophene did not lead to the expected derivatives, but to (benzo)furo- and (benzo)thieno[2,3-b]quinolines. Separate cyclization was also performed under acidic conditions on 2-(arylamino)phenones in order to obtain acridines and related compounds. Most of the synthesized compounds were screened for their antiproliferative activity in A2058 melanoma cells, and against a panel of disease-relevant kinases such as mammalian CDK5/p25, PIM1, CLK1, DYRK1A, GSK3α/β Haspin and leishmanial CK1. The biological results are reported.

Thermally induced formal [3+2] cyclization of ortho-aminoaryl-tethered alkylidenecyclopropanes: Facile synthesis of furoquinoline and thienoquinoline derivatives

We have developed a facile synthetic method to access furoquinoline and thienoquinoline derivatives via a thermally induced ring-opening and cyclization reaction from ortho-aminoaryl-tethered alkylidenecyclopropanes with the in situ generation of isocyana