(E)-3-Propoxymethyl­idene-2,3-dihydro-1H-pyrrolo[2,1-b]quinazolin-9-one monohydrate

Burkhon Zh Elmuradov; Kambarali Turgunov; Bakhodir Tashkhodjaev; Khusniddin M Shakhidoyatov

doi:10.1107/S1600536810014303

. 2010 Apr 30;66(Pt 5):o1238. doi: 10.1107/S1600536810014303

(E)-3-Propoxymethylidene-2,3-dihydro-1H-pyrrolo[2,1-b]quinazolin-9-one monohydrate

Burkhon Zh Elmuradov ^a,^*, Kambarali Turgunov ^a, Bakhodir Tashkhodjaev ^a, Khusniddin M Shakhidoyatov ^a

PMCID: PMC2979261 PMID: 21579258

Abstract

The title compound, C₁₅H₁₆N₂O₂·H₂O, was synthesized via the alkylation of 3-hydroxymethylidene-2,3-dihydro-1H-pyrrolo[2,1-b]quinazolin-9-one with n-propyl iodide in the presence of sodium hydroxide. The organic molecule and the water molecule both lie on a crystallographic mirror plane. In the crystal structure, intermolecular O—H⋯O and O—H⋯N hydrogen bonds link the components into extended chains along [100].

Related literature

For the synthesis of the title compound and its derivatives, see: Späth & Platzer, (1935 ▶); Shakhidoyatov et al. (1976 ▶); Oripov et al. (1979 ▶); Elmuradov et al. (2006 ▶); Elmuradov & Shakhidoyatov (2004 ▶); Jahng et al. (2008 ▶). For the physiological activity of the title compound and its derivatives, see: Amin & Mehta (1959 ▶); Chatterjee & Ganguly (1968 ▶); Yakhontov et al. (1977 ▶); Yunusov et al. (1978 ▶); Johne (1981 ▶); Shakhidoyatov (1988 ▶). For standard bond distances, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₅H₁₆N₂O₂·H₂O
M _r = 274.31
Monoclinic,
a = 9.247 (2) Å
b = 6.876 (1) Å
c = 10.950 (2) Å
β = 97.90 (3)°
V = 689.6 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.75 × 0.53 × 0.20 mm

Data collection

Stoe Stadi-4 four-circle diffractometer
1483 measured reflections
1479 independent reflections
1000 reflections with I > 2σ(I)
3 standard reflections every 60 min intensity decay: 2%

Refinement

R[F ² > 2σ(F ²)] = 0.064
wR(F ²) = 0.144
S = 1.15
1479 reflections
128 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Data collection: STADI4 (Stoe & Cie, 1997 ▶); cell refinement: STADI4; data reduction: X-RED (Stoe & Cie, 1997 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP (Bruker, 1998 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810014303/lh5028sup1.cif

e-66-o1238-sup1.cif^{(17KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810014303/lh5028Isup2.hkl

e-66-o1238-Isup2.hkl^{(74.4KB, 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
O1w—H1⋯N1	0.85 (7)	2.14 (8)	2.968 (5)	165 (7)
O1w—H2⋯O2ⁱ	0.90 (7)	1.95 (7)	2.855 (5)	176 (6)

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Symmetry code: (i) Inline graphic .

Acknowledgments

We thank the Academy of Sciences of the Republic of Uzbekistan for supporting this study (grant FA–F3–T047).

supplementary crystallographic information

Comment

Tricyclic quinazoline alkaloids are a large group of heterocyclic compounds (Späth & Platzer, 1935; Shakhidoyatov et al., 1976; Oripov et al., 1979; Elmuradov & Shakhidoyatov, 2006; Jahng et al., 2008). These compounds and their derivatives possess different pharmacological activities (Amin & Mehta1959; Chatterjee & Ganguly, 1968; Yakhontov et al., 1977; Yunusov et al., 1978; Johne, 1981; Shakhidoyatov, 1988).

Alkylation of 3- hydroxymethylidene-2,3-dihydro-1H-pyrrolo[2,1-b]quinazolin-9-one with C1—C3 alkyl halides leads to the formation of new C-alkyl (Elmuradov & Shakhidoyatov, 2004) or O-alkyl derivatives (Elmuradov et al., 2006). Using the typical synthesis for O-alkyl derivatives the reaction of 3- hydroxymethylidene-2,3-dihydro-1H-pyrrolo[2,1-b]quinazolin-9-one with n-propyl iodide was carried out by boiling of the initial reagents (1:2 ratio) over 7 hours in ethanol in the presence of sodium hydroxide (Elmuradov et al., 2006) (Figure 1). The compound (3-hydroxymethylidene-2,3-dihydro-1H-pyrrolo[2,1-b]quinazolin- 9-one) is obtained by formylation of 2,3-dihydro-1H-pyrrolo[2,1-b]quinazolin-9-one (alkaloid Deoxyvasicinone, isolated from Peganum Harmala) (Chatterjee & Ganguly, 1968) with Vilsmeier-Haack reagent.

The asymmetric unit contains half molecule of 3-propoxymethylidene-2,3-dihydro-1H-pyrrolo[2,1-b]quinazolin-9- one and a half water molecule (Figure 2). Both molecules of the asymetric unit lay on the crystallographic mirror plane. The water molecule links the N and Oⁱ atoms of title compound molecule by O—H···N and O—H···Oⁱ hydrogen bonds, which form a H-bond chain along [100] (Figure 3). The bond distances (Allen et al., 1987) and angles in molecule are in normal ranges.

Experimental

Sodium hydroxide (0.08 g, 2 mmol) was dissolved in ethanol (10 ml), and 3-hydroxymethylidene-2,3-dihydro-1H-pyrrolo[2,1-b]quinazolin-9-one (0.214 g, 1 mmol) and propyl iodide (0.34 g, 0.18 ml, d=1.747 g/ml, 2 mmol) were added. The mixture was heated to reflux on a water bath for 7 hours. The solvent was distilled off and the residue was re-crystallized from hexane. The title compound was obtained in 70 % yield (0.18 g). Colorless crystals suitable for X-ray analysis were obtained from hexane by slow evaporation.