Formation of cyclopropa[c]indole system in the Mn-mediated radical addition of cyclohexane-1,3-diones to N-substituted acrylamides

Yılmaz, Mehmet; Birincioğlu, Sedanur; Inal, Aslı Ustalar

doi:10.1016/j.mencom.2020.11.032

Cited by 3 publications

(1 citation statement)

References 56 publications

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“…Also, dihydrofuran compounds can be synthesized from radical cyclization of active methylene compounds with unsaturated systems via Mn(OAc) 3 . Over recent years, many works were reported about dihydrofuran compounds such as thiazolopyrimidine fused dihydrofurans, [17] cyclopropa [c]indole systems, [18] dihydrofuran-carbonitriles, [19] fluorinated-dihydrofurans [20] and dihydrofurocoumarins. [21] Due to many biological activities and applications of pyridopyrimidines and dihydrofurans, the need to develop synthetic methods for these compounds was increased.…”

Section: Introductionmentioning

confidence: 99%

Microwave Assisted Synthesis of 2,3‐Dihydro‐4H‐ furo[2,3‐d]pyrido[1,2‐a]pyrimidin‐4‐ones and furo[2,3‐d]pyrido[1,2‐a]pyrimidin‐4‐one

Yalduz

Yılmaz

2023

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In this work, furo[2,3d]pyrido [1,2-a]pyrimidin-4-ones were obtained by microwave assisted radical cyclizations of 2-hydroxy-4H-pirido[1,2a]pirimidin-4-ones with conjugated alkenes and phenylacetylene via Mn(OAc) 3. Conventional heating and microwave irradiated reaction types were compared using parameters like temperature, time and molar ratios to determine best reaction condition. Obtained compounds were purified by chromatographic methods and characterized by spectroscopic techniques ( 1 H NMR, 13 C NMR, HRMS, FTIR). Also, to determine the exact configuration and regioselectivity of isolated compounds, XRD analysis were performed.

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Section: Introductionmentioning

confidence: 99%

Microwave Assisted Synthesis of 2,3‐Dihydro‐4H‐ furo[2,3‐d]pyrido[1,2‐a]pyrimidin‐4‐ones and furo[2,3‐d]pyrido[1,2‐a]pyrimidin‐4‐one

Yalduz

Yılmaz

2023

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

et al. 2022

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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.

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Rearrangement of Methylenebis(cyclohexane-1,3-dione) Enols Induced by Mn(III)-Catalyzed Aerobic Oxidation

2022

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The Mn(III)-catalyzed aerobic oxidation of methylenebis(cyclohexane-1,3-dione) enols 1 resulted in 6a-hydroxy-2,3,4,6a,7,8,9,10a-octahydro-1H-benzo[c]chromene-1,6,10-triones 3 during the formation of 4,5,8,10,11,12-hexahydro-2H-benzo[b]oxecine-2,6,7,9(3H)-tetraones 2. The mechanism for the formation of 3 was proposed on the basis of the isolation of intermediates 2, which were transformed into 3 under Claisen and retro-Claisen conditions.

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Formation of cyclopropa[c]indole system in the Mn-mediated radical addition of cyclohexane-1,3-diones to N-substituted acrylamides

Cited by 3 publications

References 56 publications

Microwave Assisted Synthesis of 2,3‐Dihydro‐4H‐ furo[2,3‐d]pyrido[1,2‐a]pyrimidin‐4‐ones and furo[2,3‐d]pyrido[1,2‐a]pyrimidin‐4‐one

Microwave Assisted Synthesis of 2,3‐Dihydro‐4H‐ furo[2,3‐d]pyrido[1,2‐a]pyrimidin‐4‐ones and furo[2,3‐d]pyrido[1,2‐a]pyrimidin‐4‐one

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

Rearrangement of Methylenebis(cyclohexane-1,3-dione) Enols Induced by Mn(III)-Catalyzed Aerobic Oxidation

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