1,2,3-Benzotriazin-4(3H)-ones: Synthesis, Reactions and Applications

Nickel-Catalyzed Denitrogenative Cross-Coupling Reaction of 1,2,3-Benzotriazin-4(3H)-ones with Organoboronic Acids: An Easy Access to Ortho-Arylated and Alkenylated Benzamides

“…In recent years, 1,2,3-triazoles such as pyridotriazoles, N -sulfonyl-1,2,3-triazoles, 1,2,3-benzotriazinones, and N -aroylbenzotriozoles have been recognized as useful substrates to synthesize various azaheterocycles via metal-catalyzed denitrogenative transannulation reactions . In this context, Murakami et al demonstrated a series of nickel-catalyzed transannulation reaction of 1,2,3-benzotriazinones with various π-components such as alkyne, alkene, allene, benzyne, and isocyanides to prepare isoquinolones and isoindolinones. − Recently, Liu et al also demonstrated the asymmetric denitrogenative transannulation reaction of 1,2,3-benzotriazinones by synthesizing axially chiral isoquinolones in high yields with high enantioselectivity .…”

“…In this context, Murakami et al demonstrated a series of nickel-catalyzed transannulation reaction of 1,2,3-benzotriazinones with various π-components such as alkyne, alkene, allene, benzyne, and isocyanides to prepare isoquinolones and isoindolinones. − Recently, Liu et al also demonstrated the asymmetric denitrogenative transannulation reaction of 1,2,3-benzotriazinones by synthesizing axially chiral isoquinolones in high yields with high enantioselectivity . Interestingly, these reactions proceed through a five-membered aza-nickelacycle intermediate I (Figure ) which is in sharp contrast to rhodium- and palladium-catalyzed reactions of other 1,2,3-triazoles such as pyridotriazoles, N -sulfonyl-1,2,3-triazoles, and N -aroylbenzotriazoles that proceed via a metallocarbene intermediate …”

Anthra[1,2-d][1,2,3]triazine-4,7,12(3H)-triones as a New Class of Antistaphylococcal Agents: Synthesis and Biological Evaluation

“…It is known that diazotization of the corresponding ortho-amino amides with NaNO 2 or t-BuONO under slightly acidic conditions is one of the most common methods for the formation of the 1,2,3-triazin-4-one ring [15]. Despite the widespread use of this method, condensed carbocyclic 1,2,3-triazin-4-one derivatives are known only for the benzene and naphthalene systems [24]. In the context of the above, herein we report a method for the synthesis of new triazine-containing anthraquinone structures and the study their antibacterial effect for identifying potential antimicrobial agents.…”

Synthesis of ortho-Methylated Benzamides via Palladium-Catalyzed Denitrogenative Cross-Coupling Reaction of [1,2,3]-Benzotriazin-4(3H)-ones with DABAL-Me3

“…[1,2,3]-Benzotriazin-4­(3 H )-ones are an important class of N -heterocyclic compounds that find wide applications in pharmaceuticals, dyes, recording/imaging materials, fluorescence, and chemiluminescence . The cyclic triazene unit imparts high reactivity to these heterocyclic compounds and thus makes them versatile intermediates for different synthetic transformations.…”