Jump to main content
Jump to site search

Issue 84, 2015
Previous Article Next Article

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

Author affiliations

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

Back to tab navigation

Supplementary files

Article information


Submitted
10 Jul 2015
Accepted
26 Aug 2015
First published
27 Aug 2015

Chem. Commun., 2015,51, 15398-15401
Article type
Communication
Author version available

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

Social activity

Search articles by author

Spotlight

Advertisements