A novel methodology for chemoselective preparation of non-symmetric 1,3,4-oxadiazoles via PPA-assisted activation of nitroalkanes towards nucleophilic attack with acylhydrazides is developed.
We discovered a reaction of nitroalkanes with 2-hydrazinylquinolines, 2-hydrazinylpyridines and bis-2,4-dihydrazinylpyrimidines in polyphosphoric acid (PPA) affording 1,2,4-triazolo[4,3-a]quinolines, 1,2,4-triazolo[4,3-a]pyridines and bis[1,2,4]triazolo[4,3-a:4',3'-c]pyrimidines, respectively. The reaction expands the scope of heterocyclic annulations involving...
Indolizines and pyrazolo[1,5-a]pyridines were prepared via 3+2]-cycloaddition of pyridinium ylides to 1-chloro-2-nitrostyrenes. The synthesized molecules were evaluated for antiproliferative activities against a BE(2)-C neuroblastoma cell line with several compounds decreasing...
Unusual cascade transformation involving
ring opening and 1,2-alkyl
shift was observed upon the reduction of 4′H-spiro[indole-3,5′-isoxazoles] or 2-(3-oxoindolin-2-yl)acetonitriles
with sodium borohydride. This reaction allowed for expeditious and
highly efficient preparation of 2-(1H-Indol-3-yl)acetamides
with antiproliferative properties.
The mechanistic rationale involving activation of nitroalkanes towards interaction with nucleophilic reagents in the presence of polyphosphoric acid (PPA) was re-evaluated. Could nitrile oxide moieties be formed during this process?
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