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. 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.

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