Chemoselective synthesis of m-teraryls through ring transformation of 2H-pyran-2-ones by 2-(1-arylethylidene)-malononitriles
Literature Information
Publication Date
2018-10-31
DOI
10.1039/C8OB02370K
Impact Factor
3.876
Authors
Rahul Panwar, Shally, Ranjay Shaw, Amr Elagamy, Ramendra Pratap
View Original
Abstract
We have developed a simple, efficient and chemoselective approach for the synthesis of m-teraryls by the reaction of 6-aryl-2-oxo-4-(sec.amino)-2H-pyran-3-carbonitriles and 2-(1-arylethylidene)malononitriles under basic conditions. We used 6-aryl-2-oxo-4-methylsulfanyl-2H-pyran-3-carbonitriles as precursors and successfully afforded 5′-methylsulfanyl-[1,1′;3′,1′′]teraryl-4′-carbonitriles. We tried to understand the difference in the reactivity of structurally symmetrical molecules, such as allyl cyanide, 2-cyanomethylbenzonitrile and 2-(1-arylethylidene)malononitrile. The structure of 4′′-methyl-5′-(piperidin-1-yl)-[1,1′:3′,1′′-terphenyl]-4′-carbonitrile was confirmed by single crystal X-ray diffraction analysis.
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Source Journal
Organic & Biomolecular Chemistry
CiteScore:
3.4
Self-citation Rate:
10.3%
Articles per Year:
1041
Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.
Recommended Compounds
3,3'-(Piperazine-1,4-diyl)bis(2-hydroxypropane-1-sulfonic acid) Sodium Salt
CAS Number:
108321-08-0
Molecular Formula:
C20H41N4Na3O16S4
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