Org Lett. 2006 Aug 17;8(17):3805-8.

Facile one-pot synthesis of N-difluoromethyl-2-pyridone derivatives.

Source

Tsukuba Research Institute, Banyu Pharmaceutical Company, Ltd., Okubo 3, Tsukuba 300-2611, Japan. makoto_ando@merck.com

Abstract

[reaction: see text] A novel one-pot synthesis of N-difluoromethyl-2-pyridones is described. N-(Pyridin-2-yl)acetamide derivatives were excellent precursors for the preparation of N-difluoromethyl-2-pyridone derivatives. Difluoromethylation of 2-acetaminopyridine derivatives was achieved with sodium chlorodifluoroacetate as a difluorocarbene source in the presence of a catalytic amount of 18-crown-6. Subsequent in situ hydrolysis of resultant 1,2-dihydro-2-acetimino-1-difluoromethylpyridines proceeded under mild acidic conditions to afford the corresponding N-difluoromethyl-2-pyridones in moderate to good yields.

PMID:: 16898822; [PubMed - indexed for MEDLINE]

MeSH Terms, Substances

MeSH Terms

Substances

Pyridones

LinkOut - more resources

Full Text Sources

Other Literature Sources

Labome Researcher Resource - ExactAntigen/Labome

Supplemental Content

Save items

Related citations in PubMed

One-pot synthesis of 2-pyridones via chemo- and regioselective tandem Blaise reaction of nitriles with propiolates. [J Org Chem. 2009]
One-pot synthesis of 2-pyridones via chemo- and regioselective tandem Blaise reaction of nitriles with propiolates.
Chun YS, Ryu KY, Ko YO, Hong JY, Hong J, Shin H, Lee SG. J Org Chem. 2009 Oct 2; 74(19):7556-8.
One-pot combinatorial synthesis of 4-aryl-1H-thiopyrano[3,4-b]pyridine-5-one derivatives. [J Comb Chem. 2010]
One-pot combinatorial synthesis of 4-aryl-1H-thiopyrano[3,4-b]pyridine-5-one derivatives.
Yao CS, Wang CH, Jiang B, Tu SJ. J Comb Chem. 2010 Jul 12; 12(4):472-5.
A facile and efficient synthesis of polyfunctionalized pyridin-2(1H)-ones from beta-oxo amides under Vilsmeier conditions. [Org Lett. 2008]
A facile and efficient synthesis of polyfunctionalized pyridin-2(1H)-ones from beta-oxo amides under Vilsmeier conditions.
Xiang D, Wang K, Liang Y, Zhou G, Dong D. Org Lett. 2008 Jan 17; 10(2):345-8. Epub 2007 Dec 28.
Review [Advances in studies on synthesis and related chemistry of the antibacterial agent pyridonecarboxylic acids]. [Yao Xue Xue Bao. 1998]
Review [Advances in studies on synthesis and related chemistry of the antibacterial agent pyridonecarboxylic acids].
Guo HY. Yao Xue Xue Bao. 1998 Aug; 33(8):629-40.
Review Synthetic applications of chiral 2,3-dihydro-4-pyridones. [Curr Opin Drug Discov Devel. 2...]
Review Synthetic applications of chiral 2,3-dihydro-4-pyridones.
Joseph S, Comins DL. Curr Opin Drug Discov Devel. 2002 Nov; 5(6):870-80.

See reviews... See all...

Related information

Related Citations
Calculated set of PubMed citations closely related to the selected article(s) retrieved using a word weight algorithm. Related articles are displayed in ranked order from most to least relevant, with the “linked from” citation displayed first.
Substance (MeSH Keyword)
PubChem chemical substance (submitted) records that are classified under the same Medical Subject Headings (MeSH) controlled vocabulary as the current articles.

Recent activity

Clear Turn Off Turn On

Facile one-pot synthesis of N-difluoromethyl-2-pyridone derivatives.
Facile one-pot synthesis of N-difluoromethyl-2-pyridone derivatives.
Org Lett. 2006 Aug 17 ;8(17):3805-8.

PubMed

Your browsing activity is empty.

Activity recording is turned off.

Turn recording back on

PubMed

Result Filters

Display Settings:

Send to: