Bromination of Catechol

Kohn, Moritz

doi:10.1021/ja01145a519

Cited by 46 publications

(23 citation statements)

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“…The first one introduces the cyano groups prior to the crown ether synthesis (Scheme 1), while the second one builds the crown ether moiety in advance of the cyanation process (Scheme 2). Both procedures employ 4,5-dibromocatechol (1) [36,37] as starting material. Scheme 1 Scheme 2 In the first route (Scheme 1) the key compound is 1,2-dicyanocatechol (4), which has already been prepared by the Rosenmund-von-Braun reaction starting from 4,5-dibromocatechol (1) conveniently protected as an acetal derivative.…”

Section: Resultsmentioning

confidence: 99%

“…Synthesis: Compounds 1, [36,37] 4, [38] 5, [37] 8, [33] 18, [41] and 22, [17,46] have been previously described. Starting materials were purchased from Aldrich Chemical Co. and used as received without further purification.…”

Section: Eur J Org Chem 2000 2767ϫ2775 2771mentioning

confidence: 99%

“…A mixture of 1 [36,37] (5.00 g, 18.66 mmol), benzyl chloride (7.10 g, 56.00 mmol), K 2 CO 3 (15.50 g, 112.00 mmol), and ethanol (75.0 mL) was stirred under reflux for 8 h. After cooling to room temperature, the solvent was removed and the crude extracted in a mixture water/CH 2 Cl 2 . The organic solution was dried with anhydrous Na 2 SO 4 and the solvent was removed.…”

Section: 2-dibenzyloxy-45-dibromobenzene (2)mentioning

confidence: 99%

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Synthesis of Crowned Triazolephthalocyanines

et al. 2000

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The synthesis of triazolephthalocyanines bearing crown ether and aza‐crown ether substituents is described. Different substituents have been introduced on the nitrogen atom of the aza‐crown moiety to improve the solubility and the intrinsic amphiphilic character of these macrocycles. The crowned triazolephthalocyanines described have been prepared by a statistical procedure, and also by different variations of a stepwise method. Preliminary studies of the aggregation properties of one representative of this new family of compounds have also been carried out. An exhaustive study of the synthesis of the corresponding dicyano derivative precursors of the triazolephthalocyanines is displayed. Two different approaches have been used for this goal: The first one inserts the cyano groups prior to the synthesis of the crown ether moiety, while the second one builds the crown ether part of the molecule in advance of the cyanation process. The incompatibility of the Rosemund‐von‐Braun cyanation conditions and the presence of nitrogen atoms in the molecule is the main difficulty of the synthesis of these precursors.

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Section: Resultsmentioning

confidence: 99%

Section: Eur J Org Chem 2000 2767ϫ2775 2771mentioning

confidence: 99%

Section: 2-dibenzyloxy-45-dibromobenzene (2)mentioning

confidence: 99%

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Synthesis of Crowned Triazolephthalocyanines

et al. 2000

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“…of the macrocycle by hetero atoms. Whereas the tetraamino The following precursors were prepared according to literature procedures: 4,5-dibromocatechol, [24] N-tert-butyloxycarbonyl- (3,4-di-acid 11 showed only a poor phototoxicity, the serine derivacyanophenyl)alanine methyl ester, [17] 1O,2O-cyclohexylidene cattive 16 exhibits even a dark toxicity, which was concluded echol, [19] 4-iodophthalonitrile, [25] 20.8 mmol) in DMF (20 mL) at 0°C. After stirring the mixture a) Phthalocyanine 27, irradiated; b) Phthalocyanine 27, nonirradifor 1 h at 0°C, ethyl 2-bromopropionate (5.4 mL, 41.8 mmol) was ated; c) Negative control, irradiation without sensitiser added.…”

Section: In-vitro Cytotoxicity Investigationsmentioning

confidence: 99%

Synthesis of Novel Functionalised Zinc Phthalocyanines Applicable in Photodynamic Therapy

Drechsler

Pfaff

Hanack³

1999

Eur. J. Org. Chem.

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The synthesis of several new phthalonitriles 3, 9, 14, 25, 33, and 36, functionalised with carboxyl groups, including two examples of amino acid derivatives is described. All new phthalonitriles were converted into their corresponding phthalocyaninatozinc compounds. The phthalocyanines, 2,3,9,10,16,17,23,24‐octa(1‐carboxyethyloxy)phthalocyaninatozinc (5), 2,9,16,23‐tetra(2‐amino‐2‐carboxyethyl)phthalocyaninatozinc (11), 2,9,16,23‐tetra(1‐carboxy‐2‐hydroxyethylaminocarbonyl)phthalocyaninatozinc (16), 1,8,15,22‐tetra(carboxybutyl)phthalocyaninatozinc (27), 2,3,9,10,16,17,23,24‐octa(carboxyalkyl)phthalocyaninatozinc (39), and the nonidentically substituted 9,10,16,17,23,24‐hexa(carboxyalkyl)‐2‐[4‐(N‐succinimidyloxycarbonyl)butyl]phthaloyaninatozinc (41) are all sufficiently soluble in water. The nonidentically‐substituted compounds are important due to their selective binding to tumor‐selective antibodies. UV/Vis‐spectroscopy was used to investigate the effect of more or less sterically‐demanding substituents in the periphery of the phthalocyanines towards aggregation. The phototoxicity towards cancer cells of some of the new compounds was investigated in several in‐vitro experiments.

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“…15, 16 Earlier, 17, 18 we have offered routes to symmetrical alkoxydiphthalocyanine complexes and described their electrochemical characteristics. In the course of the in vestigations, we obtained symmetrical 2, 3,9,10,16,17,23,24,2´,3´,9´,10´,16´,17´,23´,24´ hexadecabenzyloxy(di phthalocyanine) complexes [(BnO) 8 Pc] 2 Ln.…”

mentioning

confidence: 99%