Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2021 Dec 15;27(70):17565-17569.
doi: 10.1002/chem.202103219. Epub 2021 Oct 22.

Metal Free Access to Polysubstituted Pyrimidines via Nitrile Activation and [2+2+2] Cycloaddition

Jinkui Chai  1 , Yu Nie  1 , Zhao Wang  2 , Li Cheng  1 , Ying-Guo Liu  3 , Junliang Wu  1
Affiliations

Metal Free Access to Polysubstituted Pyrimidines via Nitrile Activation and [2+2+2] Cycloaddition

Jinkui Chai et al. Chemistry. .

Abstract

Tf2 O mediated intermolecular / intramolecular [2+2+2] cycloaddition between alkynes and nitriles has been developed for efficient construction of polysubstituted pyrimidines and bicyclopyrimidines. In presence of Tf2 O, aza-allene species were generated in situ through nitrile activation and subsequently participated in the [2+2+2] cycloaddition, which was fully supported by deuteration experiments. The reaction had good substrate extensibility with moderate to excellent yield including trimethylsilylalkynes. The method was utilized as a synthetic tool in the preparation of a luminescent metal complex.

Keywords: [2+2+2] cycloaddition; bicyclopyrimidines; functionalized pyrimidine; metal free; nitrile activation.

PubMed Disclaimer

Similar articles

See all similar articles

References

    1. None
    1. J. M. Concello'n, E. Riego, J. R. Suárez, S. G. Granda, M. R. Díaz, Org. Lett. 2004, 6, 4499-4501;
    1. O. L. Epstein, T. Rovis, J. Am. Chem. Soc. 2006, 128, 16480-16481;
    1. K. V. Katkar, P. S. Chaudhari, K. G. Akamanchi, Green Chem. 2011, 13, 835-838;
    1. K. Niedermann, N. Früh, E. Vinogradova, M. S. Wiehn, A. Moreno, A. Togni, Angew. Chem. Int. Ed. 2011, 50, 1059-1063;

LinkOut - more resources