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Issue 84, 2015
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O-Transfer-facilitated cyclizations of propargylamides with TMSN3: selective synthesis of tetrazoles and dihydroimidazoles

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Abstract

An unprecedented formal [3+2] annulation of propargylamides with TMSN3 to deliver functionalized tetrazoles is developed. Oxygen-atom transfer (OAT) from the amide group to the C[triple bond, length as m-dash]C bond was realized via a NIS-triggered-cyclization/ring-opening cascade pathway. The OAT process enables the amide to serve as a two-atom unit in the reactions. Notably, in situ umpolung of azide occurred when terminal propargylamides were employed in this reaction, providing an array of diiodomethylated dihydroimidazoles.

Graphical abstract: O-Transfer-facilitated cyclizations of propargylamides with TMSN3: selective synthesis of tetrazoles and dihydroimidazoles

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Publication details

The article was received on 10 Jul 2015, accepted on 26 Aug 2015 and first published on 27 Aug 2015


Article type: Communication
DOI: 10.1039/C5CC05715A
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Citation: Chem. Commun., 2015,51, 15398-15401

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    O-Transfer-facilitated cyclizations of propargylamides with TMSN3: selective synthesis of tetrazoles and dihydroimidazoles

    Y. Hu, R. Yi, X. Yu, X. Xin, C. Wang and B. Wan, Chem. Commun., 2015, 51, 15398
    DOI: 10.1039/C5CC05715A

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