Regioselective annulation of nitrosopyridine with alkynes: straightforward synthesis of N-oxide-imidazopyridines.

@article{Manna2015RegioselectiveAO,
  title={Regioselective annulation of nitrosopyridine with alkynes: straightforward synthesis of N-oxide-imidazopyridines.},
  author={Srimanta Manna and Rishikesh Narayan and Christopher Golz and Carsten Strohmann and Andrey P. Antonchick},
  journal={Chemical communications},
  year={2015},
  volume={51 28},
  pages={
          6119-22
        }
}
We have developed a novel method for the regioselective annulation of 2-nitrosopyridines with variably substituted alkynes under mild reaction conditions. This approach allows the annulation of alkynes with 2-nitrosopyridines under reagent- and catalyst-free reaction conditions. The developed method shows excellent functional group tolerance and provides easy access to N-oxide-imidazo[1,2-a]pyridines. 
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Synthesis of Imidazo[1,2-a]pyridines: C-H Functionalization in the Direction of C-S Bond Formation.
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References

SHOWING 1-10 OF 62 REFERENCES
Regioselective synthesis of indoles via reductive annulation of nitrosoaromatics with alkynes.
TLDR
Indoles are produced regioselectively and in moderate yields by two new processes in a two-step sequence involving the (uncatalyzed) reaction of ArNO with alkynes, followed by reduction of the intermediate adduct.
Organocatalytic oxidative annulation of benzamide derivatives with alkynes.
TLDR
A new approach of cycloaddition under mild reaction conditions using simple catalysts, such as iodobenzene and peracetic acid, as oxidant, provided a straightforward synthesis of isoquinolones with fast reaction rate.
Metal-free annulation of arenes with 2-aminopyridine derivatives: the methyl group as a traceless non-chelating directing group.
TLDR
The unprecedented application of the methyl group of methylbenzenes as a traceless, non-chelating, and highly regioselective directing group is reported.
A direct route into fused imidazo-diazines and imidazo-pyridines using nucleophilic nitrenoids in a gold-catalyzed formal [3 + 2]-dipolar cycloaddition.
Pyridinium N-(heteroaryl)aminides can be employed as robust and practical synthetic equivalents of nucleophilic 1,3-N,N-dipoles in a formal cycloaddition onto electron-rich alkynes under gold…
Stereospecific formal [3+2] dipolar cycloaddition of cyclopropanes with nitrosoarenes: an approach to isoxazolidines.
The MgBr2-catalyzed formal [3+2] cycloaddition of donor-acceptor activated cyclopropanes with nitrosoarenes offers a novel approach to various structurally diverse isoxazolidines. The reactions,…
Unprecedented regiochemical control in the formation of aryl[1,2-a]imidazopyridines from alkynyliodonium salts: mechanistic insights.
TLDR
Successful application, using the recently described aryl(alkynyl)iodonium trifluoroacetate salts, is described, highlighting for the first time that the regioselectivity of this process is both counter-ion and concentration dependent.
Gold Catalysed Redox Synthesis of Imidazo[1,2-a]pyridine using Pyridine N-Oxide and Alkynes.
A mild, catalytic, atom economical synthesis of imidazo[1,2-a]pyridines has been developed: catalytic PicAuCl2 in the presence of an acid produces a range imidazo[1,2-a]pyridines in good yield. This…
Heteroaromatic imidazo[1,2-a]pyridines synthesis from C-H/N-H oxidative cross-coupling/cyclization.
TLDR
A novel silver-mediated highly selective C-H/N-H oxidative cross-coupling/cyclization between 2-aminopyridines and terminal alkynes has been demonstrated and by using this protocol, the marketed drug zolimidine (antiulcer) could be synthesized easily.
The nitrosocarbonyl hetero-Diels-Alder reaction as a useful tool for organic syntheses.
TLDR
The development of the nitrosocarbonyl HDA reaction and the utility of the resulting oxazine ring in the synthesis of a variety of important, biologically active molecules are described.
Catalytic enantioselective [4 + 2]-cycloaddition: a strategy to access aza-hexacycles.
TLDR
This tutorial review highlights strategies and recent advances to achieve high efficiency and selectivity through the use of organocatalysts and transition metal complexes, allowing also the extension of this transformation substrate scope.
...
1
2
3
4
5
...