In the past decades, an enormous number of reports have been dedicated towards the synthesis of nitrogen containing heterocycles. This immense interest have emerged owing to their wide varieties of pharmacological activities. The present review focused on the synthesis of isoquinoline derivatives, a family of N-heterocycles showing a broad range of structural diversity, biological and pharmaceutical activities. The progress on their synthetic strategies using versatile approaches are discussed in details.
Unsymmetrical di and triarylmethanes are generally synthesized through metal-catalyzed cross-coupling or Friedel-Crafts arylation via multistep harsh reaction conditions using pre-functionalized starting materials. These reaction protocols use pyrophoric materials like Grignard...
The Pd-catalyzed decarboxylation
and dual C(sp3)–H
bond functionalization approaches have been described for the preparation
of symmetrical and unsymmetrical 2,4-diarylpyridines. The developed
transformations were realized using nonactivated aromatic ketones
and amino acids as C–N sources. The efficacy of the catalyst
and reagent combination drives the transformation toward the formation
of desired products with high yields and selectivity. The described
reaction conditions have seduced the self-reaction of phenylalanine
via [2 + 2 + 2] cycloaddition and minimized the formation of 3,5-phenylpyridine
as a side product, whereas using glycine as a C–N source, the
corresponding 2,6-diarylpyridines were formed as minor products.
This study reports a mild and efficient synthetic protocol
for
the synthesis of symmetrical and unsymmetrical diarylmethanes (DAMs).
Using DMSO as the C1 source and TMSOTf as the Lewis acid
promoter, a series of functionalized symmetrical and unsymmetrical
DAMs were synthesized in high yields. Gratifyingly, DMSO plays a dual
role as a solvent and a C1 source and can also be replaced
with its deuterated counterpart, DMSO-d
6, enabling the incorporation of the -CD2 moiety into the
diarylmethane skeleton. The developed approach has been applied to
a wide range of substrates having various functional groups, and this
protocol has also been extended to the synthesis of an anti-breast
cancer agent and an anticoagulant agent using common feedstock compounds.
In addition, the postulated mechanism has been explicitly demonstrated
via control experiments.
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