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

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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

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Publication details

The article was received on 22 Jan 2019, accepted on 05 Feb 2019 and first published on 08 Feb 2019


Article type: Communication
DOI: 10.1039/C9OB00169G
Citation: Org. Biomol. Chem., 2019, Advance Article

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    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, Advance Article , DOI: 10.1039/C9OB00169G

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