Microwave-Assisted Solid-Liquid Phase Alkylation of Naphthols

Bálint, Erika; Kovács, Orsolya; Drahos, László; Keglevich, György

doi:10.2174/1570178611310050005

Cited by 12 publications

(6 citation statements)

References 38 publications

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“…Thereupon, the active ortho carbon of the phenol ring is joined to the allylic carbocation intermediate of the prenol. A similar alkylation mechanism was proposed for the C-acylation of phenol and naphtol derivatives catalyzed by ZnCl 2 supported on Al 2 O 3 as a catalyst under solvent-free and microwave conditions [30,31]. Also, the allylation position was primarily in the less sterically hindered position in all the isolated products.…”

Section: Chemistrysupporting

confidence: 55%

Synthesis, Anti-Phytopathogenic and DPPH Radical Scavenging Activities of C-Prenylated Acetophenones and Benzaldehydes

Osorio

Quiroz

Carvajal

et al. 2016

J. Chil. Chem. Soc.

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The syntheses of six prenylated acetophenone and benzaldehyde derivatives and their anti-phytopathogenic and antioxidant activities are reported. These compounds were obtained by electrophilic aromatic substitution (S E Ar) of the corresponding arenes and 3-methyl-2-buten-1-ol using ZnCl 2 as a Lewis acid catalyst in ethyl acetate. Reasonable to good yields were obtained based on unrecovered aromatic starting material (45-73%). All the synthesized compounds were evaluated against phytopathogenic gram-negative bacteria Agrobacterium tumefaciens, Pseudomonas syringae and Erwinia carotovora and plant fungal pathogens Botrytis cinerea, Phytophthora cinnamomi and Gibberella fujikuroi. The antioxidant activity was evaluated using the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity assay and expressed as half maximal inhibitory concentration (IC 50 ) values in µM concentrations. The antioxidant activity went from 27.20 µM to >100 µM. Compound 11 showed statistically significant inhibition of the growth of Botrytis cinerea, and compounds 13 and 15 showed statistically significant inhibition of the growth of Phytophthora cinnamomi, with respect to negative control fungal growth. All six compounds showed bacteriostatic effects against gram-negative plant pathogenic bacteria with IC 50 values between 250 and <3.9 µM.

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Section: Chemistrysupporting

confidence: 55%

Synthesis, Anti-Phytopathogenic and DPPH Radical Scavenging Activities of C-Prenylated Acetophenones and Benzaldehydes

Osorio

Quiroz

Carvajal

et al. 2016

J. Chil. Chem. Soc.

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“…The 7-hydroxy-2-phenyl-4H-chromen-4-one (2), 2-(3'hydroxyphenyl)-4H-chromen-4-one (3), and 2-(4'hydroxyphenyl)-4H-chromen-4-one (4) flavone structures were produced using the Baker-Venkataraman method [15,16]. Upon the production of these core flavone structures, modification was undertaken at the corresponding hydroxyl group through the application of microwave assisted O-alkylation [17]. Other approaches were attempted to produce the mono-flavones, such as the Mitsunobu reaction, including sonication, however these were found to be much less effective providing lower yields and requiring extensive purification [18][19][20].…”

Section: Chemistrymentioning

confidence: 99%

Microwave-Assisted Synthesis of Novel Bis-Flavone Dimers as New Anticancer Agents

Ragazzon

McGown

Ragazzon-Smith

et al. 2018

LOC

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In this study, we describe a microwave-based click chemistry method used to prepare a family of novel bis-flavone dimers. The substituted 7-hydroxy and 4’-hydroxy flavonoids were linked through a triazole ring. The compounds were easily synthesized and purified in high yields. The bisflavonoids were tested on different cell lines including HCT116, HepG2, MCF7 and MOLT-4. Several analogues showed to have anticancer activity with IC50 values in the range of 20-60 μM. Flavonoids are known for their anticancer properties and this method provides the basis for new medicinal structures.

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“…During O‐alkylations of phosphinic acids, as in that of phenols, the joint application of MW irradiation and PTC was found to be synergistic . Sensitive esters were prepared in another way .…”

Section: Reactions That Are Reluctant Under Conventional Heatingmentioning

confidence: 99%

The Impact of Microwaves on Organophosphorus Chemistry

Keglevich

2018

The Chemical Record

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A personal account on the pioneering results on microwave (MW)-assisted organophosphorus syntheses obtained in the last decade is presented. The broad spectrum of the reactions studied exemplifies the advantages of the MW technique as a green tool regarding efficiency and the simplification of catalyst systems. Theoretical calculations for a few typical models helped us to explore the scope and limitations of the application of MW irradiation.

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Microwave-Assisted Solid-Liquid Phase Alkylation of Naphthols

Cited by 12 publications

References 38 publications

Synthesis, Anti-Phytopathogenic and DPPH Radical Scavenging Activities of C-Prenylated Acetophenones and Benzaldehydes

Synthesis, Anti-Phytopathogenic and DPPH Radical Scavenging Activities of C-Prenylated Acetophenones and Benzaldehydes

Microwave-Assisted Synthesis of Novel Bis-Flavone Dimers as New Anticancer Agents

The Impact of Microwaves on Organophosphorus Chemistry

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