The Synthesis of Some Methyl-Substituted Acridinecarboxylic Acids*

Stapleton, G. E.; White, A. I.

doi:10.1002/jps.3030430402

Cited by 6 publications

(2 citation statements)

References 17 publications

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“…Starting materials, which are not specifically stated, were commercially available and used without further purifications. Compound a – c were prepared according to the reported procedure. − The ligands L a – L c were synthesized from corresponding aromatic diacid derivatives according to the scheme in Figure . Details of the synthesis procedures are described below.…”

Section: Experimental Sectionmentioning

confidence: 99%

Water Trapping of Metal–Organic Cages with Endohedral Variation

Htan

Luo

et al. 2019

Crystal Growth & Design

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A series of lantern-shaped M 2 L 4 metal−organic cages was synthesized by coordination-driven self-assembly of palladium(II) centers with aromatic amide bidentate ligands, and their crystal structures were investigated. Amide-functionalized ligands provide the complex with polar internal environment and the ability to encapsulate water. Tuning the size of the internal substituent allows to adjust the conformation of the ligand as well as to operate the pattern of counter-anions via steric effect and, further, to influence the arrangement of the encapsulated water guests. Contrary to expectations, the cage decorated with fluorine atoms only encapsulates two water molecules, whereas the cage substituted with larger methoxy groups can bind six water molecules with a chair arrangement. The enlarged capacity was attributed to the extrusion of two nitrate counter-anions from the cavity.

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Section: Experimental Sectionmentioning

confidence: 99%

Water Trapping of Metal–Organic Cages with Endohedral Variation

Htan

Luo

et al. 2019

Crystal Growth & Design

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“…These authors subsequently aromatized product 7 using Br2 in refluxing acetic acid, but the yield of anhydride 8 was only 37%. Two other research groups employed sulfur in high-boiling solvents for this same transformation [11,12], but the production of H2S and yields <70% were strong deterrents to the use of this route. We, therefore, attempted to dehydrogenate this product using 10% Pd-C in p-xylene, but found that a much larger quantity of 10% Pd-C (30 wt %) with added dimethyl maleate as a hydrogen acceptor was required to aromatize the cyclohexene-based adduct 7 to the phthalic anhydride derivative 8.…”

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confidence: 99%

4,5-Dimethylbenzene-1,2-dimethanol

Gnanasekaran

Bunce

Berlin

2014

Molbank

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An efficient and cost-effective synthesis of 4,5-dimethylbenzene-1,2-dimethanol is reported. The synthesis is accomplished in three steps with an overall yield of 80%.Aromatic rings are important scaffolds in organic synthesis. The rigid planarity of the ring system allows close positioning of reactive centers such that additional fused rings can be readily appended. We recently needed multi-gram quantities of the title compound as a building block to prepare 6,7-dimethylphthalazine for use in the synthesis of dihydrophthalazine-based antibiotics [1][2][3][4][5][6]. Though the compound is commercially available, it is quite expensive, and the supplier was unable to meet our requirements. Thus, we have designed and optimized a synthesis of this material that is both efficient and cost-effective.A review of the literature indicates that 4,5-dimethylbenzene-1,2-dimethanol (1) has been previously prepared [7]. This early route is similar to the one disclosed here, but was only carried out on a one-gram scale and gave a lower yield. The current approach (Scheme 1) can be scaled up to readily produce the target compound in batches of 12-15 grams with an overall yield of 80%.Our synthesis began with the Diels-Alder reaction of 2,3-dimethyl-1,3-butadiene (2) with dimethyl acetylenedicarboxylate (3). Heating this reaction in toluene for 2 h in a sealed pressure vessel afforded the 1,4-cyclohexadiene-based adduct 4 in 99% yield. Following removal of the solvent, the solid product was purified by triturating in hexanes and filtering. This cycloaddition has been previously OPEN ACCESS

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9‐Acridanones

Gagan

1973

Chemistry of Heterocyclic Compounds: A Series of Monographs

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The Synthesis of Some Methyl-Substituted Acridinecarboxylic Acids*

Cited by 6 publications

References 17 publications

Water Trapping of Metal–Organic Cages with Endohedral Variation

Water Trapping of Metal–Organic Cages with Endohedral Variation

4,5-Dimethylbenzene-1,2-dimethanol

9‐Acridanones

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