38756-10-4

Upstream product

• 24978-42-5 1,4-bis(4'-methoxyphenyl)-1,4-diazabuta-1,3-diene 
• 16954-74-8 (1,3-dioxoindan-2-ylidene)propanedinitrile 
• 22365-62-4 N¹,N²-di(4-chlorophenyl)acetamidine 
• 71709-26-7 N,N'-bis-(4-methoxy-phenyl)-acetamidine 
• 1152-75-6 N,N'-bis(4-methoxyphenyl)iminoformamide 
• 783-08-4 [4-(benzylideneamino)phenyl]methanol 
• 1749-04-8 N-(4-(N,N-dimethylamino)benzal)-p-anisidine 
• 173847-23-9 1-[(4-Methoxy-phenylamino)-methyl]-1H-benzoimidazole-2-thiol 

Relevant academic research and scientific papers

A new synthesis of quinoxaline, imidazolidine, indole and carbazole derivatives

Reactions of bis-benzalethylenediamine (1), N,N'-bis(aryl)- and N,N'-bis(cyclohexyl)ethane-1,2-diylidenediamines as well as N,N'-bis(aryl)benzene-1,4-diyldimethylidenediamines 2 with benzo- and naphthoquinones as well as α,β-unsaturated ketones such as 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ); 2,3,5,6-tetrachloro-1,4-benzoquinone (CHl-p); 3,4,5,6-tetrachloro-1,2-benzoquinone (CHl-o); 2,3-dichloro-1,4-naphthoquinone (DCNQ); 2,3-dicyano- l,4-naphthoquinone (DCNQ) and dicyanomethyleneindane-1,3-dione (CNIND) afforded quinoxaline, pyrazinoquinoxaline, imidazolidine, indole and carbazole derivatives as well as arylaminobenzo-, and napthoquinones.

Studies with arylaminomethylbenzimidazolethiols: Novel synthesis of 1,3-diazepino- and 1,2,4-triazepino[1,2-a] benzimidazole derivatives

The reaction of 3-(p-substituted arylaminomethyl)benzimidazole-2-thiols 1a,b with tetracyanoethylene (TCNE) afforded 1,3-diazepino[1,2-a]benzimidazole derivatives 8. 2-Hydrazinobenzimidazole 2 reacted with TCNE and dicyanomethyleneindane-1,3-dione (CNIND) to form 1,2,4-triazepino[1,2-a]benzimidazole derivatives 17 and 18.

Reaction of N1,N2-diarylamidines with dicyanomethylene compounds

2-Arylamino-2-(1,3-dioxo-2,3-dihydro-1H-inden-2-ylidene)ethanenitriles 6a-c together with the corresponding formanilides 7a-c have been obtained from the reaction of N1,N2-diarylformamidines 1a-c with 2-(1,3-dioxo-2,3-dihydro-1H-inden-2-ylidene)propanedinitrile 2 in ethyl acetate solution, while the analogous N1,N2-diarylacetamidines 8b-e with 2 gave indenoazepines 17b-e and in two cases 2-arylamino-(1,3-dioxo-2,3-dihydro-1H-inden-2-ylidene)ethanenitriles 6b,c as minor products.In contrast, 2-oxospiro-5'-carbonitriles 22b,c were obtained from the reaction of 8b,c with 2-(2-oxo-2,3-dihydro-1H-indol-2-ylidene)propanedinitrile 18.The structure assignment of spiro compound 22b has been confirmed on the basis of an X-ray crystal structure determination.

Reaction of Imines with Naphthoquinones and 2-(Dicyanomethylene)-1,3-indandione

Benzylideneanilines react with 2,3-dichloro-1,4-naphthoquinone and 2,3-dicyano-1,4-naphthoquinone to give 2-arylamino-3-chloro-1,4-naphthoquinones and 2-arylamino-3-cyano-1,4-naphthoquinones respectively together with the corresponding aldehydes.Similarly benzylideneanilines react with 2-(dicyanomethylene)-1,3-indandione to give 2-arylamino-2-(1,3-dioxo-2-indanylidene)acetonitriles.