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

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....

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Main Authors: Zeng, Zhongyi (Author) , Jin, Hongming (Author) , Song, Xinlong (Author) , Wang, Qian (Author) , Rudolph, Matthias (Author) , Rominger, Frank (Author) , Hashmi, A. Stephen K. (Author)
Format: Article (Journal)
Language:English
Published: 02 March 2017
In: Chemical communications
Year: 2017, Volume: 53, Issue: 31, Pages: 4304-4307
ISSN:1364-548X
DOI:10.1039/C7CC00789B
Online Access:Verlag, Volltext: http://pubs.rsc.org/en/content/articlepdf/2017/cc/c7cc00789b
Verlag, Volltext: http://dx.doi.org/10.1039/C7CC00789B
Verlag, Volltext: http://pubs.rsc.org/en/content/articlelanding/2017/cc/c7cc00789b
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Author Notes:Zhongyi Zeng, Hongming Jin, Xinlong Song, Qian Wang, Matthias Rudolph, Frank Rominger, A. Stephen K. Hashmi
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Summary: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.
Item Description:Gesehen am 29.08.2017
Physical Description:Online Resource
ISSN:1364-548X
DOI:10.1039/C7CC00789B

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