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Construction of 5-Aminotetrazoles via in Situ Generation of Carbodiimidium Ions from Ketones Promoted by TMSN₃/TfOH

Author:
Nimnual, Phongprapan, Tummatorn, Jumreang, Boekfa, Bundet, Thongsornkleeb, Charnsak, Ruchirawat, Somsak, Piyachat, Pawida, Punjajom, Kunlayanee
Source:
Journal of organic chemistry 2019 v.84 no.9 pp. 5603-5613
ISSN:
1520-6904
Subject:
chemical reactions, chemical structure, density functional theory, ions, ketones, organic chemistry, regioselectivity
Abstract:
A novel synthetic approach for the synthesis of 5-aminotetrazoles has been developed by employing simple ketones as substrates. This methodology involved the N₂-extrusion/aryl migration of azido complexes as the key step for the in situ generation of carbodiimidium ion, which could further react with hydrazoic acid and cyclize intramolecularly to provide 5-aminotetrazoles in good to excellent yields. In addition, the regioselectivity of the reaction was studied and rationalized by density functional theory calculations.
Agid:
6397512