(3RS,4SR)-Methyl 4-(2-chloro-5,8-dimethoxyquinolin-3-yl)-1-phenylpyrrolidine-3-carboxylate

Abstract

The mol­ecule of the title compound, C23H23ClN2O4, contains a quinolyl unit linked to a functionalized pyrrolidine system with a 3,4-trans arrangement of the substituents. The unit cell contains two stereoisomers that have the absolute stereochemistry 3S,4R and 3R,4S. The pyrrolidine ring adopts a twist conformation with pseudo-rotation parameters P = 258.2 (3)° and τ(M) = 35.3 (1)°. The packing is stabilized by C—H⋯π inter­actions and offset π–π stacking (centroid-to-centroid distance = 3.849 Å, inter­planar distance = 3.293 Å and slippage = 1.994 Å) between phenyl rings, leading to a two-dimensional network.

2-Bromoethyl 2-chloro-6-methylquinoline-3-carboxylate

“…Although extensive studies have been carried out in the past, selectivity clearly remains a common problem in radical bromination (Kikichi et al, 1998;Xu et al, 2003). In previous works, we have reported structure determination of some new quinoline derivatives (Benzerka et al, 2008;Ladraa et al, 2009;Ladraa et al, 2010). In this paper, we report the synthesis and structure determination of new compound, resulting from the radical bromination of 2-chloro-3-(1,3-dioxolan-2-yl)-6-methylquinoline, (I), under photocatalytic conditions.…”

“…For our previous work on the preparation of quinoline derivatives, see: Benzerka et al (2008); Ladraa et al (2009Ladraa et al ( , 2010. For radical bromination, see: Kikichi et al (1998); Xu et al (2003); Djerassi (1948); Newman & Lee (1972).…”

Ethyl 3-(2-chloro-5,8-dimethoxyquinolin-3-yl)-2-cyanooxirane-2-carboxylate

“…For applications of oxiranes, see: Hanson (1991); Kumar & Leelavathi (2007); Das et al (2007); Boukhris et al (1996); Ammadi et al, (1999). For our previous work on the preparation of quinoline derivatives, see: Bouraiou et al (2008); Benzerka et al (2008); Ladraa et al (2010). For weak hydrogen bonds, see: Desiraju & Steiner, (1999).…”

“…2-cyano-2-alkoxycarbonyloxiranes proved to be versatile reagents from which a large variety of compounds might be synthesized (Boukhris et al, 1996;Ammadi et al, 1999). In connection with our research program aimed at the synthesis and the biological evaluation of quinoline derivatives (Bouraiou et al, 2008;Benzerka et al, 2008;Ladraa et al, 2010), we report in this paper the synthesis and the structure determination by X-ray of a new quinoline compound where quinolyl moiety is linked to functionalized oxirane system.…”

N-Isopropyl-6-methyl-2-phenylquinoline-3-carboxamide

“…For our previous work on the preparation of quinoline derivatives, see: Benzerka et al (2008); Ladraa et al (2009); Bouraiou et al (2006Bouraiou et al ( , 2008. For the evaluation of their biological activity, see: Atwell et al (1988Atwell et al ( ,1989; Denny et al (1990); Toshima et al (1999); Mikata et al (1998); Henriksen et al (1991).…”