6880-25-7Relevant academic research and scientific papers
Iron-catalysed 1,2-aryl migration of tertiary azides
Wei, Kaijie,Yang, Tonghao,Chen, Qing,Liang, Siyu,Yu, Wei
, p. 11685 - 11688 (2020/10/19)
1,2-Aryl migration of α,α-diaryl tertiary azides was achieved by using the catalytic system of FeCl2/N-heterocyclic carbene (NHC) SIPr·HCl. The reaction generated aniline products in good yields after one-pot reduction of the migration-resultant imines.
Doing the methylene shuffle - Further insights into the inhibition of mitotic kinesin Eg5 with S-trityl l-cysteine
Abualhasan, Murad N.,Good, James A.D.,Wittayanarakul, Kitiyaporn,Anthony, Nahoum G.,Berretta, Giacomo,Rath, Oliver,Kozielski, Frank,Sutcliffe, Oliver B.,MacKay, Simon P.
experimental part, p. 483 - 498 (2012/09/10)
S-Trityl l-cysteine (STLC) is an inhibitor of the mitotic kinesin Eg5 with potential as an antimitotic chemotherapeutic agent. We previously reported the crystal structure of the ligand-protein complex, and now for the first time, have quantified the interactions using a molecular dynamics based approach. Based on these data, we have explored the SAR of the trityl head group using the methylene shuffle strategy to expand the occupation of one of the hydrophobic pockets. The most potent compounds exhibit strong (100 nM) inhibition of Eg5 in the basal ATPase assay and inhibit growth in a variety of tumour-derived cell lines.
Tertiary alcohols by tandem β-carbolithiation and N→C aryl migration in enol carbamates
Fournier, Anne M.,Clayden, Jonathan
, p. 142 - 145 (2012/02/14)
Enol carbamates (O-vinylcarbamates) derived from aromatic or α,β-unsaturated compounds and bearing an N-aryl substituent undergo carbolithiation by nucleophilic attack at the (nominally nucleophilic) β position of the enol double bond. The resulting carbamate-stabilized allylic, propargylic, or benzylic organolithium rearranges with N→C migration of the N-aryl substituent, creating a quaternary carbon α to O. The products may be readily hydrolyzed to yield multiply branched tertiary alcohols in a one-pot tandem reaction, effectively a polarity-reversed nucleophilic β-alkylation-electrophilic α-arylation of an enol equivalent.
Chemoselective Preparation of Ketones by the Grignard Reaction of N-Acylpyrazoles
Kashima, Choji,Kita, Isanobu,Takahashi, Katsumi,Hosomi, Akira
, p. 25 - 28 (2007/10/02)
N-Acylpyrazoles afford chemoselectively the corresponding ketones in good yields by the use of equimolar amounts of Grignard reagent.In the case of an optically active N-acylpyrazole, optical asymmetry was retained in comparable optical yield.Ketone formation by the Grignard reactions can be regarded as an important functionalization in a synthetic loop using pyrazoles as the auxiliary compound.
