2-Benz­yloxy-1,2,4-triazolo[1,5-a]quinazolin-5(4H)-one

Rashad Al-Salahi; Geffken Detlef; Bari Ahmed

doi:10.1107/S1600536811024962

. 2011 Jun 30;67(Pt 7):o1861. doi: 10.1107/S1600536811024962

2-Benzyloxy-1,2,4-triazolo[1,5-a]quinazolin-5(4H)-one

Rashad Al-Salahi ^a,^*, Geffken Detlef ^b, Bari Ahmed ^a

PMCID: PMC3151920 PMID: 21837225

Abstract

The title compound, C₁₆H₁₂N₄O₂, is a functionalized triazoloquinazoline with a substituted benzyloxy group attached at the 2-position of a triazole spacer. The triazoloquinazoline fused-ring system is approximately planar (r.m.s. deviation = 0.016 Å) while the benzyl substituent is perpendicular to the ring system, making a dihedral angle of 65.29 (6)°. The phenyl ring of the benzyloxy moiety is equally disordered over two sets of sites. A centrosymmetric N—H⋯N hydrogen bond connects molecules into dimers.

Related literature

For the biological activity of related compounds, see: Francis et al. (1991 ▶, 1998) ▶; Kim et al. (1998 ▶); Geffken et al. (2008) ▶. For related structures, see: Al-Salahi (2009 ▶); Al-Salahi & Geffken (2010 ▶); Berezank et al. (2008a ▶,b ▶); Ongini et al. (2001 ▶).

Experimental

Crystal data

C₁₆H₁₂N₄O₂
M _r = 292.30
Monoclinic,
a = 5.0319 (15) Å
b = 28.207 (9) Å
c = 9.408 (3) Å
β = 99.503 (5)°
V = 1317.0 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 153 K
0.50 × 0.10 × 0.03 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T _min = 0.951, T _max = 0.997
8172 measured reflections
2849 independent reflections
1679 reflections with I > 2σ(I)
R _int = 0.053

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.098
S = 0.80
2849 reflections
236 parameters
6 restraints
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811024962/kp2309sup1.cif

e-67-o1861-sup1.cif^{(17.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811024962/kp2309Isup2.hkl

e-67-o1861-Isup2.hkl^{(139.9KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811024962/kp2309Isup3.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
N1—H1⋯N4ⁱ	0.88	2.19	3.058 (2)	169

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Symmetry code: (i) Inline graphic .

Acknowledgments

We wish to express our gratitude to the Department of Chemistry, X-ray Crystallography Division of Hamburg University, and Dr Rudi Seidel, Max-Planck-Institut für Kohlenforschung, Germany, for valuable help in the preparation of the X-ray crystal structure.

supplementary crystallographic information

Comment

Heterocycles with 1,2,4-triazoloquinazoline moiety have been shown to exhibit diverse biological activities. For example, the novel 2-(furan-2-yl)-[1,2,4]triazolo[1,5-c]quinazolin-5yl-amine is effective adenosine antagonist (Kim, et al., 1998) whereas the related compound 2-(4-fluoro-phenyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-one was found to be benzodiazepine receptor antagonist (Francis, et al., 1988, 1991). In the continuation of our reesearch on triazoloquinazolines, we report herein the results of our study of cyclocondensation of dialkyl-N-cyanoimidocarbonates with hydrazinobenzoic acid. 2-alkoxy(arylkoxy)-[1,2,4]triazolo[1,5-a]quinazolin-5-ones is an excellent agent for controlling the plant growth diseases caused by fungal agents (Geffken, et al., 2008). The title compound, C₁₆H₁₂N₄O₂, (Fig. 1), consists of quinazoline (C1—C7, C16) and triazole (C8, N2—N4) rings substituted by the benzyl group (C9—C15). The phenyl ring of benzyloxy moiety is disodered over two locations where disordered atoms are in population 0.5:0.5. In the crystal structure, a pairs of intermolecular N—H···.N hydrogen bonds form centrosymmetric dimers (Table 1).

Experimental

2-Hydrazinobenzoic acid (10 mmol) was added in portion to a stirred solution of dibenzyl-N-cyanoimidocarbonate (10 mmol) in ethanol (20 mL) at 273 K. Afterwards triethylamine (30 mmol) was added dropwise over a period of 30 min. After the addition was completed, the reaction mixture was left to stirr overnight at room temperature. Acidification of the mixture was performed by conc. HCl under ice cooling followed by refluxing for 1–2 h. After cooling, the mixture was poured into ice/water, the resulting solid was filtered, washed with water and dried. Recrystallisation from tetrahydrofuran (THF) yielded 2-benzyloxy-4H-[1,2,4]triazolo[1,5-a]quinazolin-5-one as colourless crystals.