Synthesis of Tricyclic Tetrazoles by Cascade Diazotization/Intramolecular Radical C–H Heteroarylation of Arenes

A cascade diazotization/intramolecular radical C–H heteroarylation of 1-benzyloxy-5-aminotetrazoles and 1-phenethyl-5-aminotetrazoles as substrates using sodium nitrite and acetic acid without any heating, catalysis, irradiation, or electrolysis is reported. This one-pot reaction afforded the desire...

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Bibliographic Details
Published in:Journal of organic chemistry 2023-03, Vol.88 (5), p.2714-2725
Main Authors: Ha, Heun-Jong, Kim, Bora, Jo, Subin, Kim, Sugyeong, Park, Junho, Cho, Chang-Woo
Format: Article
Language:English
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Summary:A cascade diazotization/intramolecular radical C–H heteroarylation of 1-benzyloxy-5-aminotetrazoles and 1-phenethyl-5-aminotetrazoles as substrates using sodium nitrite and acetic acid without any heating, catalysis, irradiation, or electrolysis is reported. This one-pot reaction afforded the desired tricyclic tetrazole products in good yields (up to 94%) without isolation of the diazonium salt intermediate under mild reaction conditions.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c02187