Issue 26, 2014

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

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

Supplementary files

Article information

Article type
Paper
Submitted
25 Feb 2014
Accepted
16 Apr 2014
First published
16 Apr 2014

Org. Biomol. Chem., 2014,12, 4730-4737

Author version available

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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