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

Abstract

In the structures of the two enantiopure diastereoisomers of the title compound, C(20)H(18)ClN(3)O, which crystallize in different space groups, the molecules are very similar as far as bond distances and angles are concerned, but more substantial differences are observed in some torsion angles. The crystal structures of both molecules can be described as zigzag layers along the c axis. The packing is stabilized by hydrogen-bond interactions of N-H...O, C-H...Cl and C-H...pi types for 2-[(R)-2-chloro-3-quinolyl]-2-[(R)-1-(4-methoxyphenyl)ethylamino]acetonitrile, and of N-H...N, C-H...O and C-H...pi types for 2-[(S)-2-chloro-3-quinolyl]-2-[(R)-1-(4-methoxyphenyl)ethylamino]acetonitrile, resulting in the formation of two- and three-dimensional networks.

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).…”

2-Chloro-3-[(E)-(hydrazin-1-ylidene)methyl]-6-methoxyquinoline

“…For previous work on molecules with a quinolyl moiety, see: Benzerka et al (2011); Belfaitah et al (2006) Bouraiou et al (2008Bouraiou et al ( , 2011; Ladraa et al (2009). For applications of pyrazole and its derivatives, see: Mali et al (2010); Paul et al (2001).…”

“…Therefore, studies of the metal complexes are important in the search for new drugs. In previous works, we were interested in the design and synthesis of new molecules that contain a quinolyl moiety (Belfaitah et al, 2006;Bouraiou et al, 2008Bouraiou et al, , 2011Ladraa et al, 2009 andBenzerka et al, 2011). In this paper, we report the structure determination of compound resulting from an unwanted reaction of the 6-methoxy-1H-pyrazolo[3,4b]quinoline with RuCl 3 in acidic conditions.…”

2-Chloroquinoline-3-carboxylic acid

“…For our previous work on the preparation of -aminonitriles, see: Ladraa et al (2009); Belfaitah et al (2006). For the removal of chiral auxiliaries using ceric ammonium nitrate, see: Bhanu Prasad et al (2004).…”