Ethyltrans-3-(2-chloro-6,7-dimethylquinolin-3-yl)-1-cyclohexylaziridine-2-carboxylate

Abstract

The molecule of the title compound, C22H27ClN2O2, contains a quinolyl unit linked to a functionalized aziridine system with a 2,3‐trans arrangement of the substituents. The cyclo­hexyl ring adopts a chair conformation. The aziridine plane forms a dihedral angle of 51.23 (6)° with the 2‐chloro­pyridine ring of the 2‐chloro‐6,7‐dimethyl­quinolyl group. The mol­ecular structure is stabilized by intra­molecular C—H⋯O hydrogen bonds.

(E)-3-(2-Ethoxyquinolin-3-yl)-1-(2-hydroxy-6-methylphenyl)prop-2-en-1-one

“…The two rings of the quinolyl unit form a dihedral angle of 0.64 (8) and this unit forms a dihedral angle of 2.88 (6) with the benzene ring. The geometric parameters of (I) ( Table 1) are in agreement with those of other structures possessing a quinolyl substituent previously reported in the literature (Belfaitah et al, 2006;Bouraiou et al, 2007).…”

“…Molecules of these compounds are conformationally mobile, hence, a series of investigations has been concerned with a study of their three-dimensional structure (Khilya et al, 1991;Bologa et al, 1989;Furmanova et al, 1991). In the course of our ongoing program related to the synthesis and the biological evaluation of new quinoline derivatives (Lalaoui et al, 2003;Menasra et al, 2005;Belfaitah et al, 2006;Bouraiou et al, 2007), we report here the synthesis and crystal structure of the title compound, (I).…”

5,8-Dimethoxy-2-phenyl-1,4-dihydroquinoline-3-carbonitrile

“…For our previous work on the preparation of quinoline derivatives see: Benzerka et al (2008); Ladraa et al (2009Ladraa et al ( , 2010; Moussaoui et al (2002); Menasra et al (2005); Belfaitah et al (2006); Bouraiou et al (2006Bouraiou et al ( , 2007Bouraiou et al ( , 2008. For more details of quinoline reduction, see: Dauphinee & Forrest (1978); Srikrishna et al (1996); Vierhapper & Eliel (1975); Lim et al (1995).…”

“…The majority of reductions with zinc are carried out in acids: hydrochloric, sulfuric, formic and especially acetic. In previous works, we were interested in the design and synthesis of new molecules that contain a quinolyl moiety (Benzerka et al, 2008;Ladraa et al, 2009, Moussaoui et al, 2002Menasra et al, 2005;Belfaitah et al, 2006, 2007, 2008. In this paper, we report the structure determination of new compound that result from an unwanted reduction of the pyridine ring of 3-cyano-5,8-dimethoxy-2-phenylquinoline.…”

The diastereoisomers 2-[(S/R)-2-chloro-3-quinolyl]-2-[(R)-1-(4-methoxyphenyl)ethylamino]acetonitrile at 100 K

“…Amino acid derivatives are broadly useful chiral building blocks, with especially important applications in complex natural-product and combinatorial syntheses (Burk et al, 1998;Williams, 1989). In recent years, we have developed a programme devoted to the synthesis and biological evaluation of quinolyl derivatives (Benzerka et al, 2008;Bouraiou et al, 2007Bouraiou et al, , 2008. In previous work, we have reported the synthesis and stereostructure determination of 2-[(S)-2-chloro-3-quinolyl]-2-[(S)--methylbenzylamino]acetonitrile (Belfaitah et al, 2006).…”