Enhancement of the carbamate activation rate enabled syntheses of tetracyclic benzolactams: 8-oxoberbines and their 5- And 7-membered C-ring homologues
A route to the direct amidation of aromatic-ring-tetheredN-carbamoyl tetrahydroisoquinoline substrates was developed. This route enabled general access to 8-oxoberberines and their 5- and 7- membered C-ring homologues. It overcomes the undesired tandem side-reactions that result in the destruction of the isoquinoline backbone, which inevitably occurred under our previously reported superacidic carbamate activation method.
Kurouchi, Hiroaki
supporting information
p. 653 - 658
(2021/02/06)
Base-Mediated Anti-Markovnikov Hydroamidation of Vinyl Arenes with Arylamides
We investigated a base-promoted protocol for the intermolecular anti-Markovnikov hydroamidation of vinyl arenes with arylamides to furnish the arylethylbenzamides with excellent chemo- and regioselectivity. The reaction tolerates an extensive variety of functional groups and has been successfully extended with electronically varied handles, aminobenzamides, electron-rich/electron-deficient heterocyclic amides, and vinyl arenes to afford the hydroamidated products. Excellent chemoselectivity was observed for the amide group over amine. The proposed mechanism and vital role of the solvent was well supported by deuterium labeling studies and control experiments.
Ayushee,Patel, Monika,Meena, Priyanka,Jahan, Kousar,Bharatam, Prasad V.,Verma, Akhilesh K.
supporting information
p. 565 - 570
(2021/01/26)
An Efficient Catalytic Amidation of Esters Promoted by N-Heterocyclic Carbenes
An efficient NHC-catalyzed amidation between esters and amines or hydrazines is described. This strategy was tolerant for a wide scope of substrates, affording a series of amides (or hydrazides) in good to excellent yields (60-96%) under simple conditions. The approach was also used to synthesize the pharmaceutically relevant antidepressant moclobemide in 85% yield.
Chen, Ling-Yan,Wu, Mei-Fang
p. 1595 - 1602
(2019/03/26)
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