Issue 51, 2017

A nitrile-stabilized ammonium ylide as a masked C–C[double bond, length as m-dash]N synthon in heterocyclization with amidine–imine: 3-component assembly to fused pyrimidine scaffolds

Abstract

A unique reactivity of a nitrile-stabilized quaternary ammonium ylide as a masked C–C[double bond, length as m-dash]N synthon in contrast to its usual sigmatropic rearrangement has been demonstrated. Its reaction with 2-aminopyridine-derived aldimine undergoes electronically-assisted nucleophilic additions and Hofmann elimination, and provides a new method to access fused pyrimidines.

Graphical abstract: A nitrile-stabilized ammonium ylide as a masked C–C [[double bond, length as m-dash]] N synthon in heterocyclization with amidine–imine: 3-component assembly to fused pyrimidine scaffolds

Supplementary files

Article information

Article type
Communication
Submitted
17 Apr 2017
Accepted
03 Jun 2017
First published
07 Jun 2017

Chem. Commun., 2017,53, 6941-6944

A nitrile-stabilized ammonium ylide as a masked C–C[double bond, length as m-dash]N synthon in heterocyclization with amidine–imine: 3-component assembly to fused pyrimidine scaffolds

S. K. Guchhait, M. Saini, D. Sumkaria and V. Chaudhary, Chem. Commun., 2017, 53, 6941 DOI: 10.1039/C7CC02946B

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