91090-86-7Relevant academic research and scientific papers
Thiazole formation through a modified Gewald reaction
Mallia, Carl J.,Englert, Lukas,Walter, Gary C.,Baxendale, Ian R.
supporting information, p. 875 - 883 (2015/08/24)
The synthesis of thiazoles and thiophenes starting from nitriles, via a modified Gewald reaction has been studied for a number of different substrates. 1,4-Dithiane-2,5-diol was used as the aldehyde precursor to give either 2-substituted thiazoles or 2-substituted aminothiophenes depending on the substitution of the α-carbon to the cyano group.
Does the Nucleophilic Substitution of Halogen in o- and p-Halonitrobenzenes with Cyanoacetate Carbanions Proceed via Single Electron Transfer and a Nonchain Radical Process?
Makosza, Mieczyslaw,Podraza, Renata,Kwast, Andrzej
, p. 6796 - 6799 (2007/10/02)
The mechanistic pathway proposed by Zhang et al. (Zhang, X.-M.; Yang, D.-L.; Liu, Y.-C.J.Org.Chem. 1993, 58, 224) for nucleophilic substitution of halogen in o- and p-halonitrobenzenes, SET and nonchain radical process, was shown to be based on erronous e
Effects of Electron Acceptors and Radical Scavengers on Nonchain Radical Nucleophilic Substitution Reactions
Zhang, Xian-Man,Yang, Di-Lun,Liu, You-Cheng
, p. 224 - 227 (2007/10/02)
The yields of reaction products from thermal nucleophilic substitution reactions in dimethyl sulfoxide (DMSO) of six o- and p-nitrohalobenzenes (1) with sodium salt of ethyl α-cyanoacetate carbanion (2) were found to be markedly diminished by addition of small amounts of strong electron acceptors (p-dinitrobenzene, m-dinitrobenzene, and o-dinitrobenzene) (Table II), but little or no diminished effects on the yields of reaction products were observed by addition of radical scavengers ( such as galvinoxyl, nitroxyl, etc.) (Table III).The results are consistent with the conclusion that these reactions proceed via a nonchain radical nucleophilic substitution mechanism.
SYNTHESIS OF FLUORINATED DERIVATIVES OF GLUTETHIMIDE AND AMINOGLUTETHIMIDE
Hammond, Gerald B.,Plevey, Raymond G.,Sampson, Paul,Tatlow, John Colin
, p. 81 - 98 (2007/10/02)
Aminoglutethimide (1), used in the treatment of hormone dependent breast cancer, interacts with enzyme complexes desmolase and aromatase.Its action is not specific and its metabolism gives rise to toxic and non-inhibitory metabolites.The work described here explores the impact of fluorine substitution within the glutethimide (2) framework, on the enzyme inhibitory properties of aminoglutethimide.Four new fluorinated derivatives (5), (6), (8) and (9) have been prepared, in which fluorine substituents have been introduced into the phenyl ring and the ethyl side chain. 4-Fluoroglutethimide (5) and 3-trifluoroglutethimide (6) were synthesised from the corresponding fluorophenylacetonitriles (10) and (14) via sequential monoethylation, Michael addition to methyl propenoate and cyclisation.An alternative strategy, devised for the synthesis of (8), involved the monoarylation of ethyl cyanoacetate, and gave rise to the intermediate (29).Incorporation of fluorine was carried out by SF4 fluorination of the cyanoketoester (33), which was subsequently converted to the difluoroaminoglutethimide (8).For the synthesis of trifluoromethyl glutethimide (9), the trifluoromethyl group was introduced by alkylation of phenylcyanoacetate (16) with 2-iodo-1,1,1-trifluoroethane.Preliminary in vitro enzyme inhibition results have been obtained for compounds (5), (6) and (8).
