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Issue 61, 2016, Issue in Progress
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A reaction of 1,2-diamines and aldehydes with silyl cyanide as cyanide pronucleophile to access 2-aminopyrazines and 2-aminoquinoxalines

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Abstract

A new condensation reaction of ethylene-1,2-diamines or o-phenylenediamines and aromatic aldehydes with TMSCN as a cyanide-pronucleophile is documented. The reaction proceeds through a tandem sequence of desilylation, Strecker reaction, amidine-forming cyclization and dehydrogenative aromatization, and provides a straightforward synthetic route to access synthetically and biologically important motifs, 3-aryl substituted 2-aminopyrazines and 2-aminoquinoxalines. DBU with its unique function and rate-accelerating effect has made it possible to realize a reaction that involves several C–C/N/Si bond forming/breaking events. Interestingly, the protocol has enabled the desired tandem pathway, switching exclusively from usual transformations.

Graphical abstract: A reaction of 1,2-diamines and aldehydes with silyl cyanide as cyanide pronucleophile to access 2-aminopyrazines and 2-aminoquinoxalines

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Publication details

The article was received on 09 May 2016, accepted on 06 Jun 2016 and first published on 06 Jun 2016


Article type: Paper
DOI: 10.1039/C6RA12028H
RSC Adv., 2016,6, 56056-56063

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    A reaction of 1,2-diamines and aldehydes with silyl cyanide as cyanide pronucleophile to access 2-aminopyrazines and 2-aminoquinoxalines

    S. K. Guchhait, G. Priyadarshani and N. M. Gulghane, RSC Adv., 2016, 6, 56056
    DOI: 10.1039/C6RA12028H

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