Friedel-Crafts Chemistry

Oláh, George A.; Donovan, Daniel J.; Lin, Henry C.

doi:10.1142/9789812791405_0030

Cited by 145 publications

(91 citation statements)

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“…The procedures [46][47][48][49][50][51][52][53][54] described earlier for cyclialkylation of acids and alcohols with AlCl3/CH3NO2 or P2O5 or PPA catalysts were essentially followed. In all reactions, the crude oily or solid products were purified by flash column chromatography (basic alumina, EtOAc:n-hexane, 3:1, v:v) gave the pure products 1a,b, 2a-d and 3a-d.…”

Section: Friedel-crafts Cyclialkylations Proceduresmentioning

confidence: 99%

“…In recent communications [46][47][48][49][50], we have demonstrated simple alternative procedures in the construction of novel and known heterocyclic systems proving the synthetic utility of Friedel-Crafts [51][52][53][54] cyclialkylation approach. The results manifested that a number of difficult heterocyclic skeletons can be easily prepared with the advantages of short reaction time and high yield.…”

Section: Introductionmentioning

confidence: 99%

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Friedel-Crafts chemistry: Part 41. A new facile synthesis of indeno[1,2-c] pyrazoles, 2H-benzo[g]indazoles and benzo[6,7]cyclohepta[1,2-c]pyrazoles via Friedel-Crafts ring closures

2014

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Section: Friedel-crafts Cyclialkylations Proceduresmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Friedel-Crafts chemistry: Part 41. A new facile synthesis of indeno[1,2-c] pyrazoles, 2H-benzo[g]indazoles and benzo[6,7]cyclohepta[1,2-c]pyrazoles via Friedel-Crafts ring closures

2014

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“…The liquid-phase benzylation of aromatics, namely toluene, benzene, xylene, etc., using benzylating agent like benzyl chloride (BC) or benzyl alcohol is an important process for the production of mono-benzylated toluene (MBT), benzyltoluene, benzoic acid, substituted diphenyl methane, etc., especially selective synthesis of MBT, which is industrially important compounds used as pharmaceutical intermediates, fragrances, monomers for polycarbonate resins, heat-transfer fluids, aromatic solvents and fine chemicals [1][2][3][4][5][6].…”

Section: Introductionmentioning

confidence: 99%

Environmentally benign process for benzylation of toluene to mono-benzylated toluene over highly active and stable hierarchical zeolite catalyst

2015

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The liquid-phase benzylation of toluene with a benzylating agent like benzyl chloride (BC) is an important process for the production of mono-benzylated toluene (MBT), which is an industrially important compound used in pharmaceutical intermediates, fragrances, monomers for polycarbonate resins, heat-transfer fluids, aromatic solvents and fine chemicals. Selective synthesis of MBT by benzylation of toluene with BC over hierarchical micro-mesoporous-H-ZSM-5 (modified zeolite) catalyst was systematically studied for the first time. Hierarchical micro-mesoporous composites of H-ZSM-5 were obtained by treating parent H-ZSM-5 with different alkali (aq. NaOH) concentration. The synthesized catalysts were characterized by powder X-ray diffraction (XRD), BET surface area, TPAD, etc. The 100 % BC conversion with 100 % MBT selectivity was obtained over Hier-HZ-5 78 (Hierarchical H-ZSM-5) at lower molar ratio (toluene:BC) of 4:1 than 10:1 molar ratio reported, so far. The invented catalyst was also observed to be reusable for six catalytic cycles (one fresh and five recycles). The detailed optimization of process parameters such as molar ratio, catalyst loading and reaction time and temperature is also discussed.

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“…Using Friedel-Crafts alkylation methodology [19] with commercially available hydroquinone and cyclic alcohols, we synthesized four BHQ analogs with four-to seven-membered rings and determined their inhibitory potencies against SERCA activity in bioassays. An analysis of enzyme/inhibitor interactions was performed with the aid of molecular docking.…”

Section: Introductionmentioning

confidence: 99%

Hydroquinones with Conformationally Constrained Substituents: Synthesis, Characterization, and Evaluation as Calcium–ATPase Inhibitors

Paula¹,

Elam²,

Woeste³

et al. 2013

IJBBB

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Abstract-Derivatives of the compound 2,5-di-tert-butylhydroquinone (BHQ) are inhibitors of the sarco/endoplasmic reticulum calcium ATPase (SERCA). Previous work identified BHQ analogs with two alkyl substituents composed of four to six carbon atoms as the most potent representatives from this inhibitor class. In this study, we explored the effects of introducing two cycloalkyl substituents on the hydroquinone scaffold. Since these substituents have limited conformational flexibility, the entropy penalty upon binding of these compounds to SERCA was expected to be smaller than for non-cyclic BHQ analogs, potentially conveying higher inhibitory potency. We synthesized a congeneric series of four 2,5-disubstituted BHQ analogs and determined their inhibitory potencies against SERCA in bioassays. Potencies were found in the low micromolar and submicromolar concentration ranges, making the new compounds some of the most potent hydroquinone-based inhibitors to date. Computational docking facilitated a detailed analysis of enzyme/inhibitor interactions at the molecular level and showed that the entropic effect was noticeable but too small to increase potency in a substantial manner.Index Terms-Calcium homeostasis, enzyme inhibition, P-type ATPase, medicinal chemistry.

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Friedel-Crafts Chemistry

Cited by 145 publications

References 0 publications

Friedel-Crafts chemistry: Part 41. A new facile synthesis of indeno[1,2-c] pyrazoles, 2H-benzo[g]indazoles and benzo[6,7]cyclohepta[1,2-c]pyrazoles via Friedel-Crafts ring closures

Friedel-Crafts chemistry: Part 41. A new facile synthesis of indeno[1,2-c] pyrazoles, 2H-benzo[g]indazoles and benzo[6,7]cyclohepta[1,2-c]pyrazoles via Friedel-Crafts ring closures

Environmentally benign process for benzylation of toluene to mono-benzylated toluene over highly active and stable hierarchical zeolite catalyst

Hydroquinones with Conformationally Constrained Substituents: Synthesis, Characterization, and Evaluation as Calcium–ATPase Inhibitors

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