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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
Synthesis, Single-Crystal X-ray diffraction, Hirshfeld Surface Analysis, Supramolecular Properties, and Antibacterial
Ulviyya Askerova1, Abel Maharramov1, Mehmet Akkurt2
1Baku State University, Baku, Azerbaijan.
Abstract:
In the context of research into new synthetic possibilities under the conditions of catalytic olefination reaction (COR), based on (E)-2-((2-(p-tolyl)hydrazineylidene)methyl)phenol (an N-substituted phenylhydrazone), (E)-2-(2,2-dichloro-1-(phenyldiazenyl)vinyl)phenol (dichlorovinyldiazene) was synthesized. This compound undergoes a one-step conversion with ethyl alcohol to yield the corresponding (Z)-3-(2-(p-tolyl)hydrazineylidene)benzofuran-2(3H)-one. To assess its interactions with biological targets, a single-crystal X-ray diffraction structure analysis and Hirshfeld surface analysis were conducted. It was established that the molecule is nearly planar, with its conformation stabilized by intramolecular N-H…O hydrogen bonding, forming an S(6) ring motif. Intermolecular C-H…O hydrogen bonds link molecular pairs to form inversion dimers. Additionally, π⋯π stacking interactions were observed between the positively charged carbon of the furan ring (due to the oxygen injection effect) and the negatively charged center of an adjacent benzene ring. A comparative analysis of antibacterial activity was conducted in vivo against Acinetobacter baumannii BDU32, Escherichia coli BDU12, Pseudomonas aeruginosa BDU49, Klebsiella pneumoniae BDU44, and Staphylococcus aureus BDU23.
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