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Catalyst-Free Visible-Light-Promoted Cyclization of Aldehydes: Access to 2,5-Disubstituted 1,3,4-Oxadiazole Derivatives

ABSTRACT: An efficient synthesis

SUBMITTER: Li J

PROVIDER: S-EPMC8515816 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Synthesis of a series of novel 2,5-disubstituted-1,3,4-oxadiazole derivatives as potential antioxidant and antibacterial agents.

Project description:A series of novel 2,5-disubstituted-1,3,4-oxadiazole derivatives were synthesized and screened for their antimicrobial and antioxidant activities. The assay indicated that compounds 3c, 3d, and 3i exhibited comparable antibacterial and antioxidant activity with first-line drugs. The structure activity relationship and molecular docking study of the synthesized compounds are also reported.

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2,5-Bis(5-methyl-pyrazin-2-yl)-1,3,4-oxadiazole.

Project description:In the title mol-ecule, C(12)H(10)N(6)O, the dihedral angle between the two pyrazine rings [planar to within 0.009?(3) and 0.018?(3)?Å] is 5.62?(15)°. They deviate from the central oxadiazole ring [planar to within 0.005?(3)?Å] by 1.52?(16) and 5.55?(17)°, respectively. In the crystal, C-H?N inter-actions involving the pyrazine rings connect mol-ecules to form zigzag supramolecular chains propagating in [010].

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2,5-Bis(4-meth-oxy-phen-yl)-1,3,4-oxadiazole.

Project description:In the title compound, C(16)H(14)N(2)O(3), the essentially planar 1,3,4-oxadiazole ring [maximum deviation = 0.0021 (11) Å] is inclined at dihedral angles of 8.06 (6) and 11.21 (6)° with respect to the two benzene rings; the dihedral angle between the latter rings is 11.66 (5)°. In the crystal, short inter-molecular C⋯O inter-actions [2.9968 (15) Å] connect adjacent mol-ecules into chains propagating in [203]. The crystal structure is further stabilized by weak inter-molecular C-H⋯π inter-actions.

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2,5-Bis[2-(2-methoxy-ethoxy)phen-yl]-1,3,4-oxadiazole.

Project description:In the title compound, C(20)H(22)N(2)O(5), the central 1,3,4-oxadiazole ring is essentially planar [r.m.s. deviation from the best plane of 0.0011?Å] and makes dihedral angles of 4.10?(3) and 13.32?(4)° with the two benzene rings. In the crystal structure, the packing is stabilized by weak non-classical inter-molecular C-H?N hydrogen bonds, which link the mol-ecules into an extended network.

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4,4'-(1,3,4-Oxadiazole-2,5-diyl)di-pyri-dinium dibromide monohydrate.

Project description:In the title compound, C(12)H(10)N(4)O(+)·2Br(-)·H(2)O, the cation is approximately planar: the terminal rings make a dihedral angle of 7.91?(6)° with each other and dihedral angles of 6.02?(1) and 6.50?(8)° with the central ring. It is linked to the bromide anions and water mol-ecules by N-H?Br hydrogen bonds. In addition, O-H?Br and N-H?Br hydrogen bonds link these units into a three-dimensional network. C-H?N, C-H?Br and N-H?O inter-actions are also observed.

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A One-Pot Synthesis-Functionalization Strategy for Streamlined Access to 2,5-Disubstituted 1,3,4-Oxadiazoles from Carboxylic Acids.

Project description:A one-pot 1,3,4-oxadiazole synthesis-arylation strategy for accessing 2,5-disubstituted 1,3,4-oxadiazoles, from carboxylic acids, N-isocyaniminotriphenylphosphorane (NIITP), and aryl iodides, is reported. The reaction sequence, featuring a second stage copper-catalyzed 1,3,4-oxadiazole arylation, was found to tolerate (hetero)aryl, alkyl, and alkenyl carboxylic acids, and (hetero)aryl iodide coupling partners. The effectiveness of the two-stage strategy was exemplified by the late-stage functionalization of five carboxylic acid-containing APIs, and an extension to the synthesis of aminated 1,3,4-oxadiazoles using N-benzoyloxy amine coupling partners was also demonstrated.

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One-pot tandem cyclization of enantiopure asymmetric cis-2,5-disubstituted pyrrolidines: Facile access to chiral 10-heteroazatriquinanes.

Project description:A series of chiral 10-heteroazatriquinanes were synthesized from enantiopure asymmetric cis-2,5-disubstituted pyrrolidines through a one-pot tandem cyclization procedure. The structures and configurations of these new chiral 10-heteroazatriquinanes are confirmed by X-ray single-crystal diffraction analysis.

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Novel 3-Acetyl-2,5-disubstituted-1,3,4-oxadiazolines: Synthesis and Biological Activity.

Project description:The aim of our study was the two-stage synthesis of 1,3,4-oxadiazole derivatives. The first step was the synthesis of hydrazide-hydrazones from 3-methyl-4-nitrobenzhydrazide and the corresponding substituted aromatic aldehydes. Then, the synthesized hydrazide-hydrazones were cyclized with acetic anhydride to obtain new 3-acetyl-2,3-disubstituted-1,3,4-oxadiazolines. All of obtained compounds were tested in in vitro assays to establish their potential antimicrobial activity and cytotoxicity. Our results indicated that few of the newly synthesized compounds had some antimicrobial activity, mainly compounds 20 and 37 towards all used reference bacterial strains (except Klebsiella pneumoniae, Proteus mirabilis, and Pseudomonas aeruginosa) and fungi. These substances showed a strong or powerful bactericidal effect, especially against Staphylococcus spp. belonging to Gram-positive bacteria. Compound 37 was active against Staphylococcus epidermidis at minimal inhibitory concentration (MIC) = 0.48 µg/mL and was characterized by low cytotoxicity. This compound possessed quinolin-4-yl substituent in the second position of 1,3,4-oxadiazole ring and 3-methyl-4-nitrophenyl in position 5. High effectiveness and safety of these derivatives make them promising candidates as antimicrobial agents. Whereas the compound 20 with the 5-iodofurane substituent in position 2 of the 1,3,4-oxadiazole ring showed the greatest activity against S. epidermidis at MIC = 1.95 µg/mL.

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catena-Poly[[dianilinedichloridocopper(II)]-?(2)-2,5-bis-(4-pyrid-yl)-1,3,4-oxadiazole].

Project description:In the title compound, [CuCl(2)(C(6)H(7)N)(2)(C(12)H(8)N(4)O)](n), the Cu atom, located on an inversion center, is coordinated by four N atoms from two aniline ligands and two 2,5-bis-(4-pyrid-yl)-1,3,4-oxadiazole ligands. Two Cl atoms lying above and below the plane formed by these four N atoms inter-act weakly with the Cu atom [Cu-Cl = 2.7870?(7)?Å]. The trans 2,5-bis-(4-pyrid-yl)-1,3,4-oxadiazole ligands act as bridging ligands, linking adjacent Cu atoms and forming a one-dimensional coordination polymer. Two anilines coordinate with each Cu atom as terminal groups. The structure contains two classical N-H?Cl and two non-classical C-H?Cl hydrogen bonds.

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Biological Activity, Lipophilicity and Cytotoxicity of Novel 3-Acetyl-2,5-disubstituted-1,3,4-oxadiazolines.

Project description:Antibiotic resistance is now a global problem, and the lack of effective antimicrobial agents for the treatment of diseases caused by resistant microbes is increasing. The 3-acetyl-2,5-disubstituted-1,3,4-oxadiazolines presented in this article may provide a good starting point for the development of potential new effective antimicrobial agents useful in the treatment of bacterial and fungal infections. Particular attention is drawn to the 1,3,4-oxadiazole derivative marked with the number 29 with 5-nitrofuran-2-yl substituent in its chemical structure. This substance showed a strong bactericidal effect, especially against Staphylococcus spp., and no cytotoxicity to the L929 normal cell line.

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