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

Hayette Alliouche; Sofiane Bouacida; Thierry Roisnel; Ali Belfaitah

doi:10.1107/S1600536811023336

. 2011 Jun 22;67(Pt 7):o1754–o1755. doi: 10.1107/S1600536811023336

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

Hayette Alliouche ^a, Sofiane Bouacida ^b,^*, Thierry Roisnel ^c, Ali Belfaitah ^a

PMCID: PMC3152015 PMID: 21837137

Abstract

The title molecule, C₁₇H₁₅ClN₂O₅, contains a quinolyl unit linked to a functionalized oxirane system with a 2,3-trans arrangement of the substituents (ester group versus quinolyl). The structure can be described as being built up from zigzag layers parallel to (1 Inline graphic 0). The heterocyclic ring of the quinolyl unit forms a dihedral angle of 60.05 (1)° with the oxirane plane. The crystal packing is stabilized by intermolecular C—H⋯O and C—H⋯N hydrogen bonding, resulting in the formation of an infinite three-dimensional network and reinforcing the cohesion between the layers.

Related literature

For applications of quinoline derivatives, see: Kansagra et al. (2000 ▶); Vasquez et al. (2004 ▶); Guo et al. (2009 ▶) Cunico et al. (2006 ▶); Mahamoud et al. (2006 ▶); Kumar et al. (2008 ▶); Hong et al. (2010 ▶). For the biological activity of naturally occurring oxiranes, see: Bino (1980 ▶); Cross (1960 ▶); Marco-Contelles et al. (2004 ▶); Pearson & Ong (1981 ▶). 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 ▶).

Experimental

Crystal data

C₁₇H₁₅ClN₂O₅
M _r = 362.76
Triclinic,
a = 8.3784 (3) Å
b = 10.1071 (4) Å
c = 10.7027 (4) Å
α = 102.489 (2)°
β = 103.977 (2)°
γ = 96.026 (2)°
V = 846.77 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 150 K
0.28 × 0.21 × 0.12 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ▶) T _min = 0.842, T _max = 0.970
12867 measured reflections
3803 independent reflections
3369 reflections with I > 2σ(I)
R _int = 0.020

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.141
S = 1.02
3803 reflections
229 parameters
H-atom parameters constrained
Δρ_max = 0.54 e Å⁻³
Δρ_min = −0.42 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and DIAMOND (Brandenburg & Berndt, 2001 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811023336/zj2015sup1.cif

e-67-o1754-sup1.cif^{(19.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811023336/zj2015Isup2.hkl

e-67-o1754-Isup2.hkl^{(182.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811023336/zj2015Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯N19ⁱ	0.95	2.57	3.434 (3)	151
C24—H24A⋯O16ⁱⁱ	0.98	2.57	3.152 (4)	118

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

We are grateful to all personal of the PHYSYNOR Laboratory, Université Mentouri-Constantine, Algeria, for their assistance.

supplementary crystallographic information

Comment

Due to their presence in a large number of natural products and bioactive compounds and their close association with the biological activities, quinoline and their derivatives have been extensively investigated by organic and biological chemists (Kansagra et al., 2000; Vasquez et al., 2004; Guo et al., 2009). They are used in production of anti-malarial, antibiotics, anti-hypertension, anti-diabetic and so many other drugs (Cunico et al., 2006; Mahamoud et al., 2006; Kumar et al. 2008; Hong et al. 2010).

Oxiranes are important intermediates and starting materials which have found much use in synthetic organic chemistry owing to their ease of formation and ready activity toward nucleophiles (Hanson et al., 1991; Kumar et al., 2007; Das et al. 2007). In addition, natural occurring oxiranes are associated with various biological activities (Cross, 1960; Bino, 1980; Pearson et al., 1981; Marco-Contelles et al., 2004). 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. The reactivity of this compound and its analogues toward nucleophiles is under investigation.

The molecular geometry and the atom-numbering scheme of (I) are shown in Fig. 1.

In the asymmetric unit of title compound the oxiranes unit bearing an ester and cyano groups at C3 and quinolyl moiety at C2.

The two rings of quinolyl moiety are fused in an axial fashion and form a dihedral angle of 2.43 (5)°. The heterocycle ring of quinolyl unit form also with oxirane plane a dihedral angle of 60.05 (1)°.

The crystal packing can be described as layers in zig zag parallel to (1–10) plane (Fig. 2). A weak hydrogen bond interactions (C—H···N=3.434 (3) Å)along the [110] directions ensure the stability in the same layer. (as reported by Desiraju & Steiner, 1999) These layers are linked together by a classical weak C—H···O interactions and π-π stacking The crystal packing is stabilized by intra and intermolecular hydrogen bond (C—H···N and C—H···O) and π-π stacking, resulting in the formation of infinite three-dimensional network linked these layers toghter and reinforcing a cohesion of structure (Fig. 3). Hydrogen-bonding parameters are listed in table 1.

Experimental

The title compound was obtained by oxidation of (E)-ethyl-3-(2-chloro-5,8-dimethoxyquinolin-3-yl)-2-cyanoacrylate with 2,5 equivalents of m-chloroperoxybenzoic acid in dichloromethane at room temperature in the presence of 1,2 equivalents of potassium carbonate. Column chromatography (silica gel, eluant: CH₂Cl₂) of the residue afforded pure product as yellow solid. Crystals suitable for X-ray analysis were obtained by slow evaporation of a dichloromethane / methanol solution.