Issue 10, 2019

tert-Butyl nitrite-mediated radical cyclization of tetrazole amines and alkynes toward tetrazolo[1,5-a]quinolines

Abstract

A general and efficient radical cyclization of 1H-tetrazol-5-amines and alkynes toward tetrazolo[1,5-a]quinolines is established for the first time. The annulation mediated by tert-butyl nitrite takes place expeditiously within 10 minutes under mild conditions. Without using external additives or excitation, the tetrazolo[1,5-a]quinoline derivatives are obtained in moderate to good yields, along with high regioselectivities for unsymmetrical alkynes and broad functional tolerance features. The reaction is exemplified to occur via a radical process, with aryl radicals synergistically generated from tert-butyl nitrite, water and tetrazolate-diazonium salts.

Graphical abstract: tert-Butyl nitrite-mediated radical cyclization of tetrazole amines and alkynes toward tetrazolo[1,5-a]quinolines

Supplementary files

Article information

Article type
Communication
Submitted
22 Jan 2019
Accepted
05 Feb 2019
First published
08 Feb 2019

Org. Biomol. Chem., 2019,17, 2619-2623

tert-Butyl nitrite-mediated radical cyclization of tetrazole amines and alkynes toward tetrazolo[1,5-a]quinolines

T. Liu, Y. Ji and L. Wu, Org. Biomol. Chem., 2019, 17, 2619 DOI: 10.1039/C9OB00169G

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