1-Allyl-1<i>H</i>-1,3-benzimidazol-2(3<i>H</i>)-one

Belaziz, Dounia; Rodi, Youssef Kandri; Chahdi, Fouad Ouazzani; Essassi, El Mokhtar; Saadi, Mohamed; Ammari, Lahcen El

doi:10.1107/s1600536812043620

Cited by 4 publications

(6 citation statements)

References 9 publications

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“…In a previous study, we reacted benzimidazol-2-one with dodecyl bromide in the presence of a catalytic quantity of tetra-n-butylammonium bromide under mild conditions to form 1-dodecyl-1H-benzimidazol-2(3H)-one (Belaziz et al, 2012;Ouzidan et al, 2011). The study is extended to the synthesis of new benzimidazol-2-one derivative by action of methylbenzyl bromide with 1H-benzimidazol-2(3H)-one to form the title compound (Scheme 1).…”

Section: Methodsmentioning

confidence: 99%

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1-(4-Methylbenzyl)-1H-benzimidazol-2(3H)-one

Belaziz¹,

Y²,

F³

et al. 2012

Acta Cryst E

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Key indicators: single-crystal X-ray study; T = 296 K; mean (C-C) = 0.002 Å; R factor = 0.044; wR factor = 0.122; data-to-parameter ratio = 19.6.In the title compound, C 15 H 14 N 2 O, the fused five-and sixmembered ring system is essentially planar, the maximum deviation from the mean plane being 0.009 (1) Å . The benzimidazol-2(3H)-one residue is nearly perpendicular to the benzyl ring, forming a dihedral angle of 77.41 (6) . In the crystal, inversion dimers are formed by pairs of N-HÁ Á ÁO hydrogen bonds; these dimers are linked by weak C-HÁ Á ÁO interactions into a two-dimensional array in the (102) plane. Related literature Data collectionBruker X8 APEXII diffractometer 16486 measured reflections 3211 independent reflections 2157 reflections with I > 2(I) R int = 0.029

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Section: Methodsmentioning

confidence: 99%

“…For pharmacological and biochemical properties of benzimidazole derivatives, see: Lee et al (2004); Deligeorgiev et al (2011); Scott et al (2002); Gothelf et al (1998). For related structures, see: Belaziz et al (2012); Ouzidan et al (2011). Symmetry codes:…”

Section: Related Literaturementioning

confidence: 99%

1-(4-Methylbenzyl)-1H-benzimidazol-2(3H)-one

Belaziz¹,

Y²,

F³

et al. 2012

Acta Cryst E

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“…For their use as intermediates in chemical synthesis, see: Bai et al (2001). For similar compounds, see: Belaziz et al (2012Belaziz et al ( , 2013.…”

Section: Related Literaturementioning

confidence: 99%

1-Allyl-3-benzyl-1H-benzimidazol-2(3H)-one

Rodi¹,

Haoudi²,

Capet³

et al. 2013

Acta Cryst E

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In the title compound, C17H16N2O, the fused benzimidazol-2(3H)-one system is essentially planar, the largest deviation from the mean plane being 0.006 (2) Å for the carbonyl C atom. Its mean plane is almost perpendicular to the benzyl plane and to the allyl group, making dihedral angles of 80.6 (1) and 77.4 (3)°, respectively. The benzyl group and the allyl subsituent lie on opposite sides of the fused ring system. In the crystal, molecules are linked by bifurcated C—H⋯O hydrogen bonds in which the carbonyl O atom acts as accepter to two aromatic C—H groups, forming a two-dimensional network parallel to (001).

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“…As a continuation of our research work devoted to the development of substituted benzimidazol-2-one derivatives Ouzidan, Kandri Rodi, Fronczek et al, 2011;Belaziz et al 2012), we reported in this paper the synthesis of benzimidazol-2-one derivative by action of propargyl bromide with 1Hbenzo[d]imidazol-2(3H)-one in the presence of a catalytic quantity of tetra-n-butylammonium bromide under mild conditions to furnish two compounds: di-substituted (Ouzidan, Kandri Rodi, Jasinski et al, 2011) and mono-substituted (Scheme 1).…”

Section: Sup-1mentioning

confidence: 99%