Notiz zur Herstellung von Chloromethylmethylether aus Methoxyessigsäure

Stadlwieser, Josef

doi:10.1055/s-1985-31240

Cited by 32 publications

(9 citation statements)

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“…The multistep synthesis of M7 ( 7 ) was performed according to Scheme 2 and following modified versions of previously reported procedures [ 19 , 20 , 22 , 23 , 24 ].…”

Section: Resultsmentioning

confidence: 99%

“…Although chloromethylmethylether ( 1 ) is commercially available, due to its high cost, it was prepared starting from methoxyacetic acid and following one of the two procedures previously reported [ 22 ] and shown in the first step of Scheme 2 . This procedure was preferred because it did not need to separate the intermediate acylic derivative and allowed 1 to be achieved with a good degree of purity and a higher yield.…”

Section: Resultsmentioning

confidence: 99%

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Synthesis of Polystyrene-Based Cationic Nanomaterials with Pro-Oxidant Cytotoxic Activity on Etoposide-Resistant Neuroblastoma Cells

et al. 2021

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Drug resistance is a multifactorial phenomenon that limits the action of antibiotics and chemotherapeutics. Therefore, it is essential to develop new therapeutic strategies capable of inducing cytotoxic effects circumventing chemoresistance. In this regard, the employment of natural and synthetic cationic peptides and polymers has given satisfactory results both in microbiology, as antibacterial agents, but also in the oncological field, resulting in effective treatment against several tumors, including neuroblastoma (NB). To this end, two polystyrene-based copolymers (P5, P7), containing primary ammonium groups, were herein synthetized and tested on etoposide-sensitive (HTLA-230) and etoposide-resistant (HTLA-ER) NB cells. Both copolymers were water-soluble and showed a positive surface charge due to nitrogen atoms, which resulted in protonation in the whole physiological pH range. Furthermore, P5 and P7 exhibited stability in solution, excellent buffer capacity, and nanosized particles, and they were able to reduce NB cell viability in a concentration-dependent way. Interestingly, a significant increase in reactive oxygen species (ROS) production was observed in both NB cell populations treated with P5 or P7, establishing for both copolymers an unequivocal correlation between cytotoxicity and ROS generation. Therefore, P5 and P7 could be promising template macromolecules for the development of new chemotherapeutic agents able to fight NB chemoresistance.

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“…The multistep synthesis of M7 ( 7 ) was performed according to Scheme 2 and following modified versions of previously reported procedures [ 19 , 20 , 22 , 23 , 24 ].…”

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Synthesis of Polystyrene-Based Cationic Nanomaterials with Pro-Oxidant Cytotoxic Activity on Etoposide-Resistant Neuroblastoma Cells

et al. 2021

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“…However, attempts to obtain bromoacetic acid by a similar approach failed, producing silver bromide and a mixture of gases, which were identified as carbon dioxide and methyl bromide. Since then, a very few sporadic examples were reported, mentioning the introduction of the halogen function, via a decarboxylation in the very specific substrates. − These included a first halodecarboxylation of aromatic acids , which was observed by Pope and Wood upon halogenation of hydroxybenzoic acids. They subjected 4-hydroxybenzoic acid in cold sulfuric acid to bromine in an attempt to synthesize 2,6-dibromophenol, but the major isolated product from the reaction was 2,4,6-tribromophenol .…”

Section: Pioneering and Classical Methodsmentioning

confidence: 99%

Decarboxylative Halogenation of Organic Compounds

2020

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Decarboxylative halogenation, or halodecarboxylation, represents one of the fundamental key methods for the synthesis of ubiquitous organic halides. The method is based on conversion of carboxylic acids to the corresponding organic halides via selective cleavage of a carbon–carbon bond between the skeleton of the molecule and the carboxylic group and the liberation of carbon dioxide. In this review, we discuss and analyze major approaches for the conversion of alkanoic, alkenoic, acetylenic, and (hetero)aromatic acids to the corresponding alkyl, alkenyl, alkynyl, and (hetero)aryl halides. These methods include the preparation of families of valuable organic iodides, bromides, chlorides, and fluorides. The historic and modern methods for halodecarboxylation reactions are broadly discussed, including analysis of their advantages and drawbacks. We critically address the features, reaction selectivity, substrate scopes, and limitations of the approaches. In the available cases, mechanistic details of the reactions are presented, and the generality and uniqueness of the different mechanistic pathways are highlighted. The challenges, opportunities, and future directions in the field of decarboxylative halogenation are provided.

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“…Accurate mass measurements (HRMS) were made either on an AEI MS3074 spectrometer or by the Chemistry Department, University of Melbourne using a JEOL AX505H spectrometer. : 11.40 g (63%); colourless liquid; bp 109-113 °C (lit 6. 105-110 °C).…”

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confidence: 99%

The Synthesis of Tetrahydroquinolines Related to Virantmycin

Francis¹,

Williamson²,

Ward³

2004

Synthesis

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4-Substituted anilines react with 1-methoxymethyl-1-butyl-3-trimethysilylpropargyl chloride but not with 1,1-dibutyl-3-trimethylsilylpropargyl chloride, to form the corresponding substituted N-propargylanilines. These anilines cyclise, using cuprous chloride, in the presence of trifluoroacetic anhydride, and, when the aniline substituent is electron donating, to give 6-substituted 2-butyl-2-methoxymethyl-1-trifluoroacetyl-1,2-dihydroquinolines. Chlorination, followed by selective dechlorination using sodium cyanoborohydride, of the 6-methyl product yields 2-butyl-2-methoxymethyl-3-chloro-6-methyl-1-trifluoroacetyl-1,2,3,4-tetrahydroquinoline which has the same relative stereochemistry as that in the antiviral compound, Virantmycin.

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Notiz zur Herstellung von Chloromethylmethylether aus Methoxyessigsäure

Cited by 32 publications

References 0 publications

Synthesis of Polystyrene-Based Cationic Nanomaterials with Pro-Oxidant Cytotoxic Activity on Etoposide-Resistant Neuroblastoma Cells

Synthesis of Polystyrene-Based Cationic Nanomaterials with Pro-Oxidant Cytotoxic Activity on Etoposide-Resistant Neuroblastoma Cells

Decarboxylative Halogenation of Organic Compounds

The Synthesis of Tetrahydroquinolines Related to Virantmycin

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