41996-52-5

Upstream product

• 17087-90-0 N-(4-dimethylaminobenzylidene)-p-toluidine 
• 16954-74-8 (1,3-dioxoindan-2-ylidene)propanedinitrile 
• 24764-92-9 1,4-bis(p-tolyl)-1,4-diaza-1,3-butadiene 
• 16596-03-5 N,N'-di-p-tolylformamidine 
• 2272-45-9 benzal-p-toluidine 

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.

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.