3-[2-(3-Methyl­quinoxalin-2-yl­oxy)eth­yl]-1,3-oxazolidin-2-one

Caleb Anothane Ahoya; Rachid Bouhfid; Ballo Daouda; El Mokhtar Essassi; Lahcen El Ammari

doi:10.1107/S1600536810012687

. 2010 Apr 10;66(Pt 5):o1050. doi: 10.1107/S1600536810012687

3-[2-(3-Methylquinoxalin-2-yloxy)ethyl]-1,3-oxazolidin-2-one

Caleb Anothane Ahoya ^a, Rachid Bouhfid ^b, Ballo Daouda ^a, El Mokhtar Essassi ^a,^*,^‡, Lahcen El Ammari ^c

PMCID: PMC2979098 PMID: 21579110

Abstract

Two isomers were isolated during the reaction between 3-methylquinoxalin-2-one and bis(2-chloroethyl)amine hydrochloride. The crystal structure of one isomer has already been reported [Caleb, Bouhfid, Essassi & El Ammari (2009). Acta Cryst. E65, o2024–o2025], while that of the second isomer is the subject of this work. The title compound, C₁₄H₁₅N₃O₃, has a new structure containing oxazolidine and quinoxaline rings linked by an ethoxy group. The main difference between the two isomers is the position of the oxazolidine group with respect to the quinoxaline system. The dihedral angle between the fused planar rings and the oxazolidin-2-one ring is 41.63 (8)° in the title molecule.

Related literature

For the biological activity of 3-[2-(3-methyl-1,2-dihydroquinoxalin-2-yloxy)ethyl]oxazolidin-2-one, see: Madhusudhan et al. (2004 ▶); Soad et al. (2006 ▶); Sriharsha & Shashikanth (2006 ▶); Menoret et al. (2009 ▶); Wilhelmsson et al. (2008 ▶). For the structure of the isomer of the title compound, see: Caleb et al. (2009 ▶). For related structures, see: Doubia et al. (2007 ▶); Mamedov et al. (2007 ▶); Aschwanden et al.(1976 ▶)

Experimental

Crystal data

C₁₄H₁₅N₃O₃
M _r = 273.29
Triclinic,
a = 6.9936 (3) Å
b = 7.6916 (3) Å
c = 13.3709 (6) Å
α = 86.649 (2)°
β = 77.044 (2)°
γ = 71.141 (2)°
V = 663.23 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.41 × 0.33 × 0.20 mm

Data collection

Bruker X8 APEXII CCD area-detector diffractometer
15358 measured reflections
3030 independent reflections
2358 reflections with I > 2σ(I)
R _int = 0.023

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.121
S = 1.06
3030 reflections
198 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia,1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810012687/dn2552sup1.cif

e-66-o1050-sup1.cif^{(16.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810012687/dn2552Isup2.hkl

e-66-o1050-Isup2.hkl^{(148.7KB, hkl)}

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

Acknowledgments

The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray measurements.

supplementary crystallographic information

Comment

Oxazolidin-2-ones and quinoxalines are subjets of numerous articles in scientific journals concerning the development of new molecules as drug candidates such as antibacterials (Madhusudhan et al. 2004); (Sriharsha & Shashikanth, 2006), anti-viral (Wilhelmsson, et al. 2008), anti-tumor (Soad et al.2006),and anti-inflammatory (Menoret et al. 2009). Our investigation is intended to increase the biological activity of such molecules. During the synthesis, two isomers were isolated, and the structure of isomer 1 has already been published (Caleb et al. 2009) while that of ismer 2 is the subject of the present work.

The structure of the 3-(2-(3-methyl-1,2-dihydro-quinoxalin-2-yloxy)ethoxy) oxazolidin-2-one molecule is also built up from two fused six-membered rings linked to a five-membered ring (oxazolidin-2-one) by an ethoxy group, as shown in Fig.1. It would be interesting to compare the crystal structures of both isomers of this compound (scheme 1). Actually, the geometric parameters (bond lenghths and angles) of the two isomers are very similar to those observed in other heterocyclic structures (Aschwanden et al., 1976; Doubia et al., 2007; Mamedov et al., 2007). However, the main difference between the two isomers is the position of the oxazolidine group with respect to the quinoxalin. Moreover, the dihedral angle between the fused six-membered rings and the five cycles measuring 20.04 (9)° in the isomer 1 instead of 41.63 (8)° in the isomer 2.

Experimental

In a 100 ml flask, is reacted 0.0125 moles of quinoxalin-2-one with 2.66 moles of dichloroethylamine hydrochloride in 40 ml of dimethyl formamide in presence of 2.87 moles of potassium carbonate and a few milligrams of tetran-butyl ammonium bromide. The mixture was brought to reflux in a sand bath, magnetic stirring and the reaction progress was monitored by thin layer chromatography. After evaporation of solvent under reduced pressure, the residue obtained is chromatographed on silica column (hexane / acetate: 4 / 6). Thus we have isolated two compounds. Recrystallization occurred in the same eluent. This compound was obtained in 38% and his melting point is 169°C.