Synthesis of Substituted 2-Pyridyl-4-phenylquinolines

Abstract

The acid-catalyzed condensation of o-aminobenzophenones with aromatic acetyl derivatives, in a basic methanol/tetrahydrofuran medium, has been used to prepare a series of substituted 2-pyridyl-4-phenylquinolines. Derivatives having two aza binding sites can act as asymmetric bidendate ligands to complex transition metals such as ruthenium, osmium or iridium. All the compounds were characterized by elemental analysis, Ei or FAB (+) MS, 1H- and 13C-NMR spectroscopies. Complete assignments of the 1H spectra were accomplished by using a combination of one- and two-dimensional NMR techniques.

Copper promoted synthesis of substituted quinolines from benzylic azides and alkynes

“…1). [16][17][18][19][20][21] Many of the classical methods, such as Ptzinger, Skraup, Friedlander, Doebner von Miller, Conrad-Limbach, and Combes reactions, known for the synthesis of quinolines are limited by harsh reaction conditions, limited substrate scope and low yields. 22 Among the various synthetic strategies, 23,24 Lewis acid promoted tandem cyclization reaction of N-aryl imines with terminal alkynes under oxidative condition allows access to a variety of 2,4-disubstituted quinolines.…”

Synthesis and photophysical properties of a novel soluble polyquinoline

“…4b). The literature reports that fully conjugated polyquinolines [29], like poly(aryl ether-phenylquinoxaline)s show a Tg ranging from 230 to 315 1C [32]. Nevertheless, Tg in the range of 110-160 1C was also reported for quinoline-based copolymers when aliphatic substituents were introduced in the quinolinic rings to improve the solubility [33].…”

Conformationally-constrained indeno[2,1-c]quinolines – a new class of anti-mycobacterial agents

“…Synthesis of the conformationally-constrained indeno[2,1c]quinoline molecules started with 2-amino-5-bromobenzophenone 21 (1, Scheme 1). Treatment of benzophenone 1 21 with malonic acid in POCl 3 gave quinoline 2 (<20%) and unreacted benzophenone 1.…”

“…Synthesis of the conformationally-constrained indeno[2,1c]quinoline molecules started with 2-amino-5-bromobenzophenone 21 (1, Scheme 1). Treatment of benzophenone 1 21 with malonic acid in POCl 3 gave quinoline 2 (<20%) and unreacted benzophenone 1. Optimization of reaction conditions however improved the yield of quinoline 2 (53%) along with the desired conformationally-locked indeno[2,1-c]quinoline 3 (16%) as a result of Friedel-Crafts cyclization of 2.…”

“…Optimization of reaction conditions however improved the yield of quinoline 2 (53%) along with the desired conformationally-locked indeno[2,1-c]quinoline 3 (16%) as a result of Friedel-Crafts cyclization of 2. The yield of indeno[2,1-c]quinoline 3 (84%) was however improved by intramolecular Friedel-Crafts acylation (AlCl 3 ) 21…”