A distinctive N-substituent controlled electrophilic N-transfer of oxaziridines with donor-acceptor cyclopropanes in the presence of MgI is reported. Contrary to earlier reports, the oxaziridine having bulkier N-substituents can also give N-transferred product instead of the O-transferred one. Interestingly, the oxaziridines having α-H containing N-substituents lead to the pyrrolidine derivatives through [3 + 2] cycloaddition. A mechanistic reasoning for this divergent reactivity is depicted by density functional theory calculations and validated through energy decomposition analysis.
An efficient MgI2-catalyzed annulation between donor-acceptor cyclopropane and N-tosylaziridinedicarboxylate to access highly substituted 2H-furo[2,3-c]pyrrole bearing two rings and four stereocenters, including one quaternary carbon stereocenter, has been developed. This methodology can be used for the synthesis of biologically active compounds like IKM-159. This work also offers an insight into the mechanism of the annulation process.
A ruthenium(II)-catalyzed cross dehydrogenative
annulation of N-(7-azaindole)benzamides with maleimides
has been demonstrated.
Herein, we have explored the use of N-amino-7-azaindole
as a new bidentate directing group for dehydrogenative [4 + 2] annulation.
This method works efficiently, affording a variety of pharmacologically
useful 7-azaindole-based isoquinolones and showing a wide functional
group tolerance.
The ruthenium(II)-catalyzed regioselective
annulation of N-(7-azaindole)amides with 1,3-diynes
has been demonstrated.
Bioactive N-amino-7-azaindole has been used as a
new bidentate directing group to furnish an array of 3-alkynylated
isoquinolones. Furthermore, the developed protocol works efficiently
for both aryl- and heteroaryl-substituted amides producing a range
of pharmacologically useful 7-azaindole-based isoquinolones with a
wide range of functionality.
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