15825-89-5Relevant articles and documents
Synthesis of N-Alkylpyridin-4-ones and Thiazolo[3,2- a]pyridin-5-ones through Pummerer-Type Reactions
Huang, Jingjia,Hu, Gang,An, Shaoyu,Chen, Dongding,Li, Minglei,Li, Pingfan
, p. 9758 - 9769 (2019/08/08)
N-Alkylated 4-pyridones were obtained through a one-pot procedure involving either normal or interrupted Pummerer reactions between triflic anhydride-activated sulfoxides and 4-fluoropyridine derivatives, followed by hydrolysis. On the other hand, triflic anhydride-activated benzyl 6-fluoro-2-pyridyl sulfoxide could react with alkenes or alkynes to afford thiazolo[3,2-a]pyridin-5-ones, via the pyridinium salt intermediates.
Expedient synthesis of gem-dialkylbenzyl heterocycles through olefinic hydroarylation
Lian, Yajing,Burford, Kristen,Londregan, Allyn T.
, p. 9509 - 9514 (2015/11/18)
A robust approach to gem-dialkylbenzyl heterocycles has been developed through a triflic acid-catalyzed hydroarylation of olefinic heterocycles. A broad range of substrates containing pyridine, quinoline, pyrazole, triazole and imidazole moieties are shown to be highly compatible with this method. This rapid construction of gem-dialkyl groups should be useful in the synthesis of drug-like molecules containing heterocyclic diversity and in the study of the gem-dialkyl effect.
Access to "friedel-Crafts-Restricted" tert -alkyl aromatics by activation/methylation of tertiary benzylic alcohols
Hartsel, Joshua A.,Craft, Derek T.,Chen, Qiao-Hong,Ma, Ming,Carlier, Paul R.
, p. 3127 - 3133 (2012/05/20)
Herein we describe a two-step protocol to prepare m-tert-alkylbenzenes. The appropriate tertiary benzylic alcohols are activated with SOCl2 or concentrated HCl and then treated with trimethylaluminum, affording the desired products in 68-97% yields (22 examples). This reaction sequence is successful in the presence of a variety of functional groups, including acid-sensitive and Lewis-basic groups. In addition to t-Bu groups, 1,1-dimethylpropyl and 1-ethyl-1-methylpropyl groups can also be installed using this method.