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6-Bromo-1,3-di-2-propynyl-1H-imidazo[4,5-b]pyridin-2(3H)-one.

ABSTRACT: The room-temperature reaction of propargyl bromide and 6-bromo-1,3-dihydro-imidazo[4,5-b]pyridin-2-one in dimethyl-formamide yields the title compound, C(12)H(8)BrN(3)O, which features nitro-gen-bound propynyl substituents. The imidazopyridine fused ring is almost planar (r.m.s. deviation = 0.011 Å); the propynyl chains point in opposite directions relative to the fused ring. One acetyl-enic H atom is hydrogen bonded to the carbonyl O atom of an inversion-related mol-ecule, forming a dimer; adjacent dimers are linked by a second acetyl-ene-pyridine C-H⋯N inter-action, forming a layer motif.

SUBMITTER: Dahmani S

PROVIDER: S-EPMC2983980 | biostudies-literature |

REPOSITORIES: biostudies-literature

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6-Bromo-1,3-dimethyl-1H-imidazo[4,5-b]pyridin-2(3H)-one.

Project description:The non-H atoms of the two independent mol-ecules in the asymmetric unit of the title compound, C(8)H(8)BrN(3)O, are planar (r.m.s. deviations = 0.015 and 0.019?Å). In the crystal, the mol-ecules are linked into a zigzag chain along the c axis by C-H?O hydrogen bonds.

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Project description:In the title compound, C14H16BrN3O5, the N atoms adjacent to the carbonyl group in the five-membered ring are substituted by (1,3-dioxolan-2-yl)methyl groups. The fused ring system is essentially planar, with the largest deviation from the mean plane being 0.014 (2) Å for the C atom bearing the Br atom. The first oxolane ring, attached on the side of the N atom belonging to the pyridine ring, has an envelope conformation with one of the O atoms as the flap, whereas the second oxolane ring displays a twisted boat conformation. The two oxolane rings display envelope and twisted boat conformations. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds, building chains parallel to the a-axis direction.

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6-Bromo-3-methyl-1H-imidazo[4,5-b]pyridin-2(3H)-one.

Project description:The title compound, C(7)H(6)BrN(3)O, was obtained from the reaction of 6-bromo-1H-imidazo[4,5-b]pyridin-2(3H)-one with methyl iodide. All non-H atoms lie in a common plane [r.m.s deviation = 0.017?(1)?Å]. The amino group is a hydrogen-bond donor to the carbonyl group of an inversion-related mol-ecule, the pair of hydrogen bonds giving rise to a hydrogen-bonded dimer.

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1-Acetyl-6-bromo-1H-imidazo[4,5-b]pyridin-2(3H)-one.

Project description:The two fused five- and six-membered rings in the mol-ecule of the title compound, C(8)H(6)BrN(3)O(2), are approximately coplanar, the largest deviation from the mean plane being 0.011?(3)?Å at the NH atom. The acetyl group is slightly twisted with respect to the imidazo[4,5-b]pyridine system, making a dihedral angle of 2.7?(2)°. In the crystal, adjacent mol-ecules are linked by inter-molecular N-H?N and C-H?O hydrogen bonds, forming infinite chains.

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Project description:The fused imidazole and pyridine rings in the title compound, C13H10BrN3O, are linked to a benzyl group. The fused ring system is essentially planar, the largest deviation from the mean plane being 0.006 (2) Å. The phenyl ring is not coplanar with the fused ring system, as indicated by the dihedral angle of 67.04 (12)°. In the crystal, mol-ecules are linked by pairs of N-H⋯O hydrogen bonds, forming inversion dimers.

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1,3-Dibenzyl-6-bromo-1H-imidazo[4,5-b]pyridin-2(3H)-one.

Project description:The imidazopyridine fused-ring in the title compound, C(20)H(16)BrN(3)O, is planar (r.m.s. deviation = 0.011?Å). The phenyl rings of the benzyl substitutents twist away from the central five-membered ring in opposite directions; the rings are aligned at 61.3?(1) and 71.2?(1)° with respect to this ring.

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6-Bromo-1-[2-(2-oxo-1,3-oxazolidin-3-yl)eth-yl]-1H-imidazo[4,5-b]pyridin-2(3H)-one.

Project description:The title compound, C(11)H(11)BrN(4)O(3), features an ethane fragment substituted with an almost planar (r.m.s. deviation = 0.019?Å) imidazo[4,5-b]pyridone ring system and an envelope-shaped oxazolidine unit on separate C atoms. The N-CH(2)-CH(2)-N torsion angle is 52.5?(4)°. In the crystal, pairs of mol-ecules are linked by N-H?O hydrogen bonds into centrosymmetric dimers.

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3-Allyl-6-bromo-1H-imidazo[4,5-b]pyridin-2(3H)-one.

Project description:In the mol-ecule of the title compound, C(9)H(8)BrN(3)O, the fused-ring system is almost planar, the largest deviation from the mean plane being 0.008?(3)?Å. The plane through the atoms forming the allyl group is roughly perpendicular to the imidazo[4,5-b]pyridin-2-one system, as indicated by the dihedral angle between them of 70.28?(11)°. In the crystal, each mol-ecule is linked to its symmetry equivalent about the center of inversion by a pair of strong N-H?O hydrogen bond, forming inversion dimers.

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6-Bromo-1-(1,2-propadien-yl)-3-(2-propyn-yl)-1H-imidazo[4,5-b]pyridin-2(3H)-one.

Project description:The reaction of propargyl bromide and 6-bromo-1,3-dihydro-imidazo[4,5-b]pyridin-2-one in refluxing dimethyl-formamide yields the title compound, C(12)H(8)BrN(3)O, which features nitro-gen-bound propadienyl and propynyl substituents. The imidazolopyridine fused ring is planar (r.m.s. deviation = 0.012?Å); the propadienyl chain is coplanar with the fused ring as it is conjugated with it, whereas the propynyl chain is not as the nitro-gen-bound C atom is a methyl-ene linkage. The acetyl-enic H atom is hydrogen bonded to the carbonyl O atom of an adjacent mol-ecule, forming a helical chain runnning along the b axis.

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