Manganese(III) Acetate‐Based Radical Cyclization Reactions for Pyranocoumarin and Pyranoquinoline Compounds: Synthesis, DFT and Molecular Docking Studies

Abstract

Pyranofuroquinoline and pyranofurocoumarin derivatives are significant class of compounds due to being useful in many diverse applications. The synthesis of the compounds are succeeded in one step by radical cyclization reaction in the presence of manganese(III) acetate. Furoquinoline and furocoumarin reactants were used together with 1,1‐disubstituted‐, 1,2‐disubstituted and cyclic alkenes giving pyranofuroquinoline and pyranofurocoumarin compounds in moderate to high yields. Also, we were able to isolate alkenyl and acetoxy‐ side‐products in minor low yields. The electronic and optical features of furoquinoline and furocoumarin reactants and pyranofuroquinoline products were inquired using theoretical approaches (DFT and TD‐DFT). Their excitation and emission spectrums were computed. The results revealed that the pyranofuroquinoline molecules did not show the energy transfer feature. It was observed that the behavior of nonlinear optic of furoquinoline is higher than the pyranofuroquinoline and furocoumarin molecules. But the average polarization and the anisotropy of the polarizability of pyranofuroquinoline increased and was found to be 262.7 and 141.9 respectively. Also, according to the calculated docking parameters, the investigated pyranofuroquinoline and pyranofurocoumarin compounds were found to have higher activity than the substances with anticancer and antibacterial standards.

Glycerol group substituted bis(2-pyridylimino)isoindoline (BPI) complexes: synthesis, characterization and investigation of their biological properties

“…Computational studies were conducted to optimize the bond lengths and angles of molecules using the DFT principle with Orca 5.0 software. 16,24,25 The Avogadro program [26][27][28] was utilized to visualize and draw the structure of the ligands. The geometry of the compounds in the gas phase was optimized at the DFT [29][30][31] level using the hybrid functional PBE0 with the def2-SVP basis set.…”

Recent Advances in Manganese(III)-Assisted Radical Cyclization for the Synthesis of Natural Products: A Comprehensive Review

“…Similarly, aldehydes, ketones, monocarboxylic acids and their anhydrides, β-dicarbonyl compounds (such as β-diketones), β-keto esters, β-keto carboxylic acids and amides, malonic acid and its derivatives, and β-nitro carbonyl compounds are oxidized by manganese(III) acetate to attain a variety of products [15]. Manganese(III) mediation in reactions not only provides oxidative cyclization [16][17][18][19][20][21][22][23][24][25][26][27][28][29], but also enables highly diversified acetoxidation [30][31][32][33][34], halogenation [35,36], aromatization [37][38][39], oxidation [40,41], phosphonation [42,43], epoxidation [44], and also polymerization [45]. Cyclization occurs via two different mechanisms: intermolecular and intramolecular.…”

“…Conversely, 24b produced 25b and 27 in a 13% yield (1:1 mixture of regioisomers) and diacetate 28 in a 12% yield [57]. Magolan and Kerr successfully synthesized the indole derivative (±)-mersicarpine (31) through a synthetic procedure involving a radical addition to the double bond of N-acryl indole (29) to form the tricyclic skeleton (30) (Scheme 9). This step can be considered the key synthesis step.…”