Issue 61, 2016, Issue in Progress

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

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

Supplementary files

Article information

Article type
Paper
Submitted
09 maí 2016
Accepted
06 jún. 2016
First published
06 jún. 2016

RSC Adv., 2016,6, 56056-56063

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements