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tert-Butyl nitrite-mediated radical cyclization of tetrazole amines and alkynes toward tetrazolo[1,5-a]quinolines.
Organic & Biomolecular Chemistry 2019 Februrary 16
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.
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