2-(2-Chloro-8-methyl­quinolin-3-yl)-4-phenyl-1,2-di­hydro­quinazoline

Chamseddine Derabli; Raouf Boulcina; Sofiane Bouacida; Hocine Merazig; Abdelmadjid Debache

doi:10.1107/S1600536813029334

. 2013 Oct 31;69(Pt 11):o1719–o1720. doi: 10.1107/S1600536813029334

2-(2-Chloro-8-methylquinolin-3-yl)-4-phenyl-1,2-dihydroquinazoline

Chamseddine Derabli ^a, Raouf Boulcina ^a, Sofiane Bouacida ^b,^c,^*, Hocine Merazig ^b, Abdelmadjid Debache ^a

PMCID: PMC3884366 PMID: 24454142

Abstract

In the title compound, C₂₄H₁₈ClN₃, the dihydroquinazoline and methyl-substituted quinoline benzene rings make a dihedral angle of 78.18 (4)° and form dihedral angles of 45.91 (5) and 79.80 (4)°, respectively, with the phenyl ring. The dihedral angle between the phenyl ring of dihydroquinazoline and the methyl-substituted benzene ring of quinoline is 78.18 (4)°. The crystal packing can be described as crossed layers parallel to the (011) and (0-11) planes. The structure features N—H⋯N hydrogen bonds and π–π interactions [centroid–centroid distance between phenyl rings = 3.7301 (9) Å].

Related literature

For the preparation and applications of quinazoline and quinoline derivatives, see: Jenekhe et al. (2001 ▶); Hoemann et al. (2000 ▶); Connolly et al. (2005 ▶); Besson et al. (2007 ▶); Roma et al. (2000 ▶); Chen et al. (2001 ▶); Debache et al. (2008 ▶, 2009 ▶); Nemouchi et al. (2012 ▶). graphic file with name e-69-o1719-scheme1.jpg

Experimental

Crystal data

C₂₄H₁₈ClN₃
M _r = 383.86
Monoclinic,
a = 14.4553 (13) Å
b = 8.7501 (9) Å
c = 16.8630 (16) Å
β = 119.696 (6)°
V = 1852.8 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 150 K
0.12 × 0.04 × 0.02 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ▶) T _min = 0.959, T _max = 1.000
10282 measured reflections
3276 independent reflections
2894 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.031
wR(F ²) = 0.082
S = 1.06
3276 reflections
254 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Data collection: APEX2 (Bruker, 2011 ▶); cell refinement: SAINT (Bruker, 2011 ▶); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg & Berndt, 2001 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536813029334/hg5353sup1.cif

e-69-o1719-sup1.cif^{(28.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813029334/hg5353Isup2.hkl

e-69-o1719-Isup2.hkl^{(157.5KB, hkl)}

Click here for additional data file.^{(7.3KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813029334/hg5353Isup3.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
N3—H3N⋯N2ⁱ	0.86	2.26	3.0998 (18)	165

Open in a new tab

Symmetry code: (i) Inline graphic .

Acknowledgments

We are grateful to all personnel of the Laboratoire de Synthèse des Molécules d’intérêts Biologiques and UR–CHEMS, Université Constantine 1, Algeria, for their assistance. Thanks are due to the MESRS (Ministère de l’Enseignement Supérieur et de la Recherche Scientifique, Algeria) for financial support.

supplementary crystallographic information

1. Comment

It is well known that the quinoline ring system is an important structural unit widely existing in alkaloids, therapeutics and synthetic analogues with interesting biological activities (Roma et al., 2000; Chen et al., 2001). In addition quinolines are valuable synthons for the preparation of nano- and meso-structures with enhanced electronic and photonic functions (Jenekhe et al., 2001). Due to their importance as substructures in a broad range of natural and designed products, significant efforts continue to be directed into the development of new quinoline-based structures (Hoemann et al., 2000). In the other hand, the quinazoline unit represents a useful natural product scaffold with demonstrated activities against numerous disorders. The transferable nature of its properties provides a strong rationale for the development of synthetic methods. Not surprisingly, considerable progress in synthetic methodology applicable to quinazoline alkaloids has been made during the past decade (Connolly et al., 2005; Besson et al., 2007). As part of our research in developing new efficient methods for heterocycles synthesis and also multicomponent reactions (Debache et al., 2008; Debache et al., 2009; Nemouchi et al., 2012), we decided to design some new molecules containing reactive fonctionnalities. As a result of this investigation we report herein a fast and efficient protocol for the synthesis of 2-(2-Chloro-8-methylquinolin-3-yl)-4-phenyl-1,2-dihydroquinazoline via a three-component reaction between 2-aminobenzophenone, 2-chloro-8-methylquinoline-3-carbaldehyde, and ammonium acetate, completed by the X-ray structure analysis.

The molecular geometry and the atom-numbering scheme of (I) are shown in Fig. 1. The benzene ring of dihydroquinazoline and methyl-substituted benzene rings of quinoline form a dihedral angles of 45.91 (5) and 79.80 (4)° respectively with a phenyl ring group. The dihedral angle between the phenyl ring of dihydroquinazoline and methyl-substituted benzene rings of quinoline is 78.18 (4) °. The crystal packing can be described as crossed layers parallel to the (011) and (0–11) planes. (Fig. 2). It is stabilized by a N—H···N hydrogen bond (Table 1, Fig. 2) and π-π interactions. however the centroid to centroid small distance between the phenyl rings is 3.7301 (9) Å. These interactions link the molecules within the layers and also link the layers together and reinforcing the cohesion of the structure.

2. Experimental

A mixture of 2-chloro-8-methylquinoline-3-carbaldehyde (1.0 equiv), 2-aminobenzophenone (1.0 equiv), ammonium acetate (2.0 equiv), and 4-(N,N-dimethylamino)pyridine (0.2 equiv.) in 5 ml of absolute ethanol was stirred at 40°C. After completion of the reaction as monitored by TLC, the reaction mixture was poured into ice cold water; solid product was filtered, washed with water (3–5 ml) and dried. The crude product was recrystallized from ethyl acetate to give pure dihydroquinazoline as a yellow solid; m.p. 182–184 °C; IR (KBr) ν 3329, 1605, 1551, 1470, 1315, 1080, 756, 698 cm-1; 1H NMR (CDCl3, 250 MHz) δ 8.52 (s, 1H, arom.), 7.74–7.41 (m, 8H, arom.), 7.34–7.26 (m, 2H, arom.), 6.83–6.74 (m, 2H, arom.), 6.48 (s, 1H, CH), 4.79 (s, 1H, NH), 2.81 (s, 3H, CH3); 13 C NMR (CDCl3, 62.5 MHz) δ 167.4, 148.2, 146.8, 146.6, 139.3, 138.0, 136.4, 133.2, 132.6, 130.9, 129.9, 129.3, 123.0, 128.4, 127.5, 127.1, 126.1, 120.4, 118.9, 117.9, 114.8, 68.8, 18.0. Anal. calcd for C₂₄H₁₈N₃Cl: C, 75.09; H, 4.73; N, 10.95; Found: C, 75.18; H, 4.94; N, 11.37. HRMS calcd f or C₂₄H₁₉N₃Cl (MH+) 384.1189; found 384.1162.