59523-27-2

Upstream product

• 120914-37-6 Benzoic acid N,N'-dimethyl-N'-(2-nitro-phenyl)-hydrazide 
• 120914-33-2 1,2-dimethyl-3-phenyl-1,2-dihydro-1,2,4-benzotriazine 
• 120914-36-5 N,N'-Dimethyl-N-(2-nitro-phenyl)-hydrazine 
• 98-88-4 benzoyl chloride 
• 2622-63-1 1-methyl-2-phenylbenzimidazole 
• 36016-40-7 mesitylenesulfonylhydroxylamine 

Downstream Products

• 120914-32-1 1-methyl-2-phenylbenzimidazolium 3-(4-nitrobenzoyl)imide 

Relevant academic research and scientific papers

Synthesis and Thermal Reactions of 1,2-Dihydro-1,2,4-benzotriazines

The 1,2-dimethyl-1,2,4-benzotriazines (7),(8), and (9) were prepared by acid-catalysed cyclisation of the 2-aminophenylhydrazine derivatives derived from (12), (13), and (14) respectively.Compounds (7) and(9) undergo a thermal elimination to fully aromatic benzotriazines.However, the 2-acyl derivative (18) rearranges to the thermodynamically more stable 4-acyl compound (21).In the presence of traces of water, a ring contraction to benzimidazoles is a competing reaction.For (18) the nitrogen fragment is retained in the benzamide (22).A mechanism for the ring contraction has been suggested in which initial hydration of the imine bond gives 1,2,3,4-tetrahydrobenzotriazines which ring-open, then re-cyclise to benzimidazoles.The benzimidazophthalazine (23) was shown not to be an intermediate in the water-mediated ring contraction of (18).