NaNO2/I2 as an alternative reagent for the synthesis of 1,2,3-benzotriazin-4(3H)-ones from 2-aminobenzamides

[Display omitted] •NaNO2/Iodine mediated transformation of 2-aminobenzamides to 1,2,3-benzotriazine-4(3H)-ones.•Acid-free efficient method with broad substrate scope.•Accommodates unsubstituted 2-aminobenzamides and substrate bearing acid-labile Boc-group.•Ionic mechanism via nitrosylation of amino...

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Bibliographic Details
Published in:Tetrahedron letters 2019-01, Vol.60 (3), p.248-251
Main Authors: Barak, Dinesh S., Mukhopadhyay, Sushobhan, Dahatonde, Dipak J., Batra, Sanjay
Format: Article
Language:English
Subjects:
1,2,3-Benzotriazin-4-one
2-Aminobenzamide
Iodine
Nitrogen heterocycle
Sodium nitrite
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Summary:[Display omitted] •NaNO2/Iodine mediated transformation of 2-aminobenzamides to 1,2,3-benzotriazine-4(3H)-ones.•Acid-free efficient method with broad substrate scope.•Accommodates unsubstituted 2-aminobenzamides and substrate bearing acid-labile Boc-group.•Ionic mechanism via nitrosylation of amino group. An efficient transformation of 2-aminobenzamides to 1,2,3-benzotriazin-4(3H)-ones in the presence of sodium nitrite (NaNO2) and Iodine (I2) is described. The reaction is proposed to proceed via formation of nitrosyl halide that induces nitrosylation of the amino group of 2-aminobenzamide leading to diazotization followed by intramolecular cyclization.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2018.12.025