3659-76-5

Upstream product

• 97810-87-2 N-[1]naphthyl-benzamide oxime 
• 100-44-7 benzyl chloride 
• 85-84-7 1-phenylazo-2-naphthylamine 
• 10146-04-0 1-p-Tolylazo-naphthalen-2-ylamine 
• 5316-02-9 1-Anilino-2-phenylnaphth<1,2-d>imidazole 
• 108979-84-6 1-[2]naphthyl-5-phenyl-1H-tetrazole 
• 644-13-3 C₆H₅COC₁₀H₇ 
• 38396-17-7 N-(2-nitro-[1]naphthyl)-benzamide 
• 10224-78-9 1-(2'-nitrobenzeneazo)-2-amino-naphthalene 
• 607-54-5 N-(naphthalen-1-yl)benzimidamide 
• 13672-18-9 benzyl-2-naphthylamine 
• 938-25-0 1,2-diaminonaphthalene 
• 98-88-4 benzoyl chloride 
• 606-57-5 1-nitro-2-naphthylamine 

Downstream Products

• 109571-80-4 2-cyclohexyl-6,7,8,9-tetrahydro-1⁽³⁾H-naphth[1,2-d]imidazole 

Relevant academic research and scientific papers

Syntheses of condensed imidazoles by lead tetraacetate oxidation of amidines

2-Phenylbenzimidazoles, 2-benzylbenzimidazoles, 2-phenyl-1H-naphtholimidazole, and 2-benzyl-1H-naphtholimidazole have been synthesized in excellent yields (77-98percent) by lead tetraacetate oxidation of suitable N-arylbenzimides, N-arylphenylacetamidines, N-α-naphthylbenzimidine, and N-α-naphthylphenylacetamidine respectively.The mechanism of nitrene insertation and intramolecular competitive nitrene insertation leading to these heterocycles has also been discussed.

Thermal and Photochemical Transformations of 1-(Arylazo)-N-arylidene-2-naphthylamines

1-(Arylazo)-N-arylidene-2-naphthylamines 3a-e, prepared by the reaction of 1-(arylazo)-2-naphthylamines 1a,b with aromatic aldehydes 2a-d on refluxing in toluene, gave the corresponding 1-(arylamino)-2-phenylnaphthimidazoles 6a-e in yields ranging between 50 and 60percent.Refluxing of 3a in o-dichlorobenzene, however, gave 1H-2-phenylnaphthimidazole (7, 45percent) and 2H-2-phenylnaphthotriazole (9, 5percent).Reaction of 3a with dimethyl acetylenedicarboxylate gave dimethyl benzoquinoxaline-2,3-dicarboxylate (10, 11percent), dimethyl-α-benzal-α'-imino>succinate (11, 7percent), dimethyl aminofumarate (12, 2percent), and benzanilide (13, 6percent).The reaction of 1-(phenylazo)-2-naphthylamine (1a) with DMAD, however, gave 10 (32percent) and 12 (3percent).Photolysis of 3a in benzene gave 2H-2-phenylnaphthotriazole (9, 5percent) and N-benzoyl-1-(phenylazo)-2-naphthylamine (19, 41percent), whereas the photolysis in methanol gave a mixture of 6a (10percent), 19 (25percent), 1a (1percent), and the naphthotriazole 9 (4percent).Reasonable mechanisms have been suggested for the formation of the various products in these reactions.