2-Eth­oxy-5-methylbis[1,2,4]triazolo[1,5-a:4′,3′-c]quinazoline

Rashad Al-Salahi; Detlef Geffken; Ahmed Bari

doi:10.1107/S1600536811052810

. 2011 Dec 14;68(Pt 1):o101. doi: 10.1107/S1600536811052810

2-Ethoxy-5-methylbis[1,2,4]triazolo[1,5-a:4′,3′-c]quinazoline

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

PMCID: PMC3254449 PMID: 22259388

Abstract

The title compound, C₁₃H₁₂N₆O, is a functionalized ditriazoloquinazoline with substituted ethoxy and methyl groups attached at the 2-position of each triazole spacer. The fused-ring system is essentially planar [r.m.s. deviation = 0.016 (2) Å]. In the crystal, a weak C—H⋯N hydrogen bond connects the molecules into a chain along [101].

Related literature

For the biological activity of quinazoline derviatives, see: Alagarsamy et al. (2005 ▶, 2007 ▶). For our study of the chemical and pharmacological properties of triazolo quinazoline derivatives, see: Al-Salahi (2009 ▶); Al-Salahi et al. (2010 ▶, 2011 ▶); Berezank et al. (2008a ▶,b ▶). For related structures, see: El-Tombary et al. (1999 ▶).

Experimental

Crystal data

C₁₃H₁₂N₆O
M _r = 268.29
Monoclinic,
a = 7.4121 (11) Å
b = 19.240 (3) Å
c = 9.3096 (14) Å
β = 109.051 (2)°
V = 1254.9 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 153 K
0.43 × 0.21 × 0.05 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T _min = 0.959, T _max = 0.995
2851 measured reflections
2851 independent reflections
1817 reflections with I > 2σ(I)
R _int = 0.053

Refinement

R[F ² > 2σ(F ²)] = 0.055
wR(F ²) = 0.134
S = 0.91
2851 reflections
183 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.24 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: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811052810/is5002sup1.cif

e-68-0o101-sup1.cif^{(22.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811052810/is5002Isup2.hkl

e-68-0o101-Isup2.hkl^{(140KB, hkl)}

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
C3—H3⋯N4ⁱ	0.95	2.60	3.533 (2)	166

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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 for their valuable help in the determination of the X-ray crystal structure.

supplementary crystallographic information

Comment

Recently, the triazolo-annelated quinazoline compounds were found to display remarkable pharmacological activities (Alagarsamy et al., 2005, 2007). The novel 2-alkoxy-1,2,4-triazolo[1,5-a]quinazolines have been proven as excellent agents for controlling the plant growth diseases caused by fungal pathogen agents (Berezank et al., 2008a,b), and described as adenosine receptor antagonists (Al-Salahi et al., 2011). Furthermore, the bis-[1,2,4]triazolo[4,3 - a:4',3'-c]quinazoline has been reported to exhibit antitoxoplasmosis activity (El-Tombary et al., 1999). This work has done in continuation of our program with the aim of obtaining an interesting series of bis-[1,2,4]triazoloquinazolines compounds which could be expected to contribute as a pharmacophore to the bioactivity of their triazoloquinazoline parent compounds (Al-Salahi et al., 2009, 2010).

Experimental

A mixture of 2-ethoxy-5-chloro-[1,2,4]triazolo[1,5-a]quinazoline (1 mmol) and acetohydrazide (2.2 mmol) was refluxed in absolute toluene (15 ml) in the presence of sodium hydride (0.8 mmol) for 18 h. The solvent was removed under reduced pressure, and the residue was crystallized from methanol to afford (C₁₃H₁₂N₆O) as yellowish crystal.