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Issue 26, 2014
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Synthesis of 1-amino-2-aroyl/acetylnaphthalenes through a base mediated one pot inter and intramolecular C–C bond formation strategy

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Abstract

A new precursor 2-(1-cyano-2,2-bis(methylthio)vinyl)benzonitrile has been synthesized by the reaction of 2-cyanomethylbenzonitrile, carbon disulfide and methyl iodide under basic conditions. The reaction of 2-(1-cyano-2,2-bis(methylthio)vinyl)benzonitrile with various functionalized aryl/heteroaryl methyl ketones or acetone under basic conditions afforded 4-amino-3-aroyl/heteroaroyl/acetyl-2-methylsulfanylnaphthalene-1-carbonitriles in good yields through a (5C + 1C) annulation strategy; this involves sequential intermolecular, followed by intramolecular, C–C bond formation reactions. The structure of the product was confirmed by single crystal X-ray crystallography.

Graphical abstract: Synthesis of 1-amino-2-aroyl/acetylnaphthalenes through a base mediated one pot inter and intramolecular C–C bond formation strategy

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Publication details

The article was received on 25 Feb 2014, accepted on 16 Apr 2014 and first published on 16 Apr 2014


Article type: Paper
DOI: 10.1039/C4OB00432A
Citation: Org. Biomol. Chem., 2014,12, 4730-4737
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    Synthesis of 1-amino-2-aroyl/acetylnaphthalenes through a base mediated one pot inter and intramolecular C–C bond formation strategy

    S. Singh, P. Yadav, S. N. Sahu, I. Althagafi, A. Kumar, B. Kumar, V. J. Ram and R. Pratap, Org. Biomol. Chem., 2014, 12, 4730
    DOI: 10.1039/C4OB00432A

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