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Issue 31, 2017
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Gold-catalyzed intermolecular cyclocarboamination of ynamides with 1,3,5-triazinanes: en route to tetrahydropyrimidines

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Abstract

Gold-catalyzed regioselective cyclocarboamination of ynamides with 1,3,5-triazinanes opens a facile and modular access to valuable 5-aminotetrahydropyrimidines in good to excellent yields. It constitutes an unprecedented yet challenging annulation of ynamides with unstrained saturated heterocycles. This new protocol is distinguished by easy operation, readily available starting materials, stable four-atom building units, good functional-group compatibility and scaling-up potential. The preliminary mechanistic studies indicate that the present intermolecular cyclocarboamination arises from a pseudo-three-component [2+2+2] cycloaddition.

Graphical abstract: Gold-catalyzed intermolecular cyclocarboamination of ynamides with 1,3,5-triazinanes: en route to tetrahydropyrimidines

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Publication details

The article was received on 30 Jan 2017, accepted on 02 Mar 2017 and first published on 02 Mar 2017


Article type: Communication
DOI: 10.1039/C7CC00789B
Citation: Chem. Commun., 2017,53, 4304-4307
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    Gold-catalyzed intermolecular cyclocarboamination of ynamides with 1,3,5-triazinanes: en route to tetrahydropyrimidines

    Z. Zeng, H. Jin, X. Song, Q. Wang, M. Rudolph, F. Rominger and A. S. K. Hashmi, Chem. Commun., 2017, 53, 4304
    DOI: 10.1039/C7CC00789B

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