Details

Autor(en) / Beteiligte

• Barak, Dinesh S.
• Mukhopadhyay, Sushobhan
• Dahatonde, Dipak J.
• Batra, Sanjay

Titel

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

Ist Teil von

• Tetrahedron letters, 2019-01, Vol.60 (3), p.248-251

Ort / Verlag

Elsevier Ltd

Erscheinungsjahr

2019

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• [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.