Organic Letters 2011-11-18

Facile one-pot direct arylation and alkylation of nitropyridine N-oxides with Grignard reagents.

Fang Zhang, Xin-Fang Duan

Index: Org. Lett. 13(22) , 6102-5, (2011)

Full Text: HTML

Abstract

Facile arylation and alkylation of nitropyridine N-oxides were developed through the reactions of Grignard reagents with nitropyridine N-oxides. For the same 4-nitropyridine N-oxide, arylation occurred at the 2- (or 6-) position, whereas alkylation occurred at the 3-position in an adjustably site-selective manner. The cooperative action of the two groups was discovered in the reactions of 3-nitropyridine N-oxides. This protocol can find wide applications in building various pyridine compounds as illustrated in total syntheses of Emoxipin and Caerulomycin A and E.


Related Compounds

  • 4-Nitropyridine N...

Related Articles:

Pseudomonas aeruginosa Biofilm Formation and Persistence, along with the Production of Quorum Sensing-Dependent Virulence Factors, Are Disrupted by a Triterpenoid Coumarate Ester Isolated from Dalbergia trichocarpa, a Tropical Legume.

2015-01-01

[PLoS ONE 10 , e0132791, (2015)]

At a supra-physiological concentration, human sexual hormones act as quorum-sensing inhibitors.

2013-01-01

[PLoS ONE 8(12) , e83564, (2013)]

DNA double-strand break repair in parental chromatin of mouse zygotes, the first cell cycle as an origin of de novo mutation.

2008-07-01

[Hum. Mol. Genet. 17(13) , 1922-37, (2008)]

Well-known quorum sensing inhibitors do not affect bacterial quorum sensing-regulated bean sprout spoilage.

2007-03-01

[J. Appl. Microbiol. 102(3) , 826-37, (2007)]

Reduced bacterial deposition and attachment by quorum-sensing inhibitor 4-nitro-pyridine-N-oxide: the role of physicochemical effects.

2010-07-20

[Langmuir 26(14) , 12089-94, (2010)]

More Articles...