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1,2,3-Benzotriazin-4(3H)one is used to prepare 3-methoxymethyl-3H-benzo[d][1,2,3]triazin-4-one by reacting with dimethoxymethane. Further, it undergoes thermal condensation with alfa-amino acids to give 3H-1,4-benzodiazepin-(1H,4H)-2,5-diones. In addition to this, it is employed as a reagent to synthesize 1,2,3-bBenzotriazin-4-one-arylpiperazine derivatives.
Thermolysis with loss of N2 gives a reactive keteneimine intermediate which undergoes [4+2] cycloaddition reactions: Tetrahedron Lett., 3465 (1966). For similar reaction with scheme, see Isatoic anhydride, A14603.
Wang, H.; Yu, S. Synthesis of Isoquinolones Using Visible-Light-Promoted Denitrogenative Alkyne Insertion of 1,2,3-Benzotriazinones. Org. Lett. 2015, 17 (17), 4272-4275.
Fang, Z. J.; Zheng, S. C.; Guo, Z.; Guo, J. Y.; Tan, B.; Liu, X. Y. Asymmetric Synthesis of Axially Chiral Isoquinolones: Nickel-Catalyzed Denitrogenative Transannulation. Angew. Chem. Int. Ed. 2015, 127 (33), 9664-9668.
Gefahrenhinweise (EU): H301-H332-H361
Toxic if swallowed. Harmful if inhaled. Suspected of damaging fertility or the unborn child.
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