5805-74-3

Upstream product

• 143-33-9 sodium cyanide 
• 98711-52-5 1-methyl-3-(1-methyl-1,2,4-triazol-4-ylio)benzimidazolium bis-(methyl sulphate) 
• 1632-83-3 1-Methylbenzimidazole 
• 19158-51-1 P-toluenesulfonyl cyanide 
• 35342-95-1 1-methyl-2-trimethylsilanyl-1H-benzoimidazole 
• 75318-43-3 4,5-dichloro-1,2,3-dithiazolium chloride 
• 4760-34-3 N-methyl-1,2-phenylenediamine 
• 75106-99-9 4-(benzimidazol-1-yl)-4H-[1,2,4]triazole 
• 773837-37-9 sodium cyanide 
• 34734-15-1 1-methyl-2-iodo-1H-benzo[d]imidazole 
• 1849-02-1 2-chloro-1-methyl-benzimidazole 

Downstream Products

• 43102-10-9 1-Methyl-2-thiocarbamoylbenzimidazol 

Relevant academic research and scientific papers

Synthesis and in vitro cytotoxic evaluation of some thiazolylbenzimidazole derivatives

A novel kind of thiazolylbenzimidazole derivatives were designed and synthesized and evaluated for their antitumor activity against SMMC-7721 and A549 cell lines. Most compounds showed good antitumor activities, and compound 11b displayed remarkable in vi

Copper-catalyzed cyanation of heterocycle carbon-hydrogen bonds

A method for regioselective cyanation of heterocycles has been developed. A number of aromatic heterocycles as well as azulene can be cyanated in reasonable to good yields by using a copper cyanide catalyst and an iodine oxidant.

New route to 2-cyanobenzimidazoles

N-Monosubstituted 1,2-diaminobenzenes 4 (R = Me, Ph, PhCH2, and 3,4- Me2C6H3CH2) react with 4,5-dichloro-1,2,3-dithiazolium chloride 1 in dichloromethane at room temperature to give the corresponding 2- cyanobenzimidazoles 6. If pyridine is added at the beginning of the reaction, the intermediate imino-1,2,3-dithiazoles 5 can be isolated. Upon thermolysis, most of the imines 5 give the 2-cyanobenzimidazoles 6 in fair to good yields. 1.2-Diaminobenzene can be converted in high yield into the mono-imine 5i or the bis-imine 12, R = H; thermolysis of 5i gives 2-cyanobenzimidazole in high yield. Conversion of 5 into 6 involves the loss of both sulfur atoms and with the N-phenylimino derivative 5b singlet diatomic sulfur, S2, has been intercepted with norbornene and with 2.3-diphenylbutadiene to give the expected cycloadducts 7 and 8.

Synthesis of heteroarenecarbonitriles by electrophilic cyanation; Reaction of metalated heteroarenes with p-toluenesulfonyl cyanide

Several heteroarenecarbonitriles (5) were synthesized in moderate yields from heteroarenes (3) through metalation, followed by electrophilic cyanation using p-toluenesulfonyl cyanide. Similarly, trimethylsilylheteroarenes (8) were converted to heteroarenecarbonitriles (5) in good yields by treatment with p-toluenesulfonyl cyanide.

Direct synthesis of 2-cyanobenzimidazoles and the generation of S2

2-Cyanobenzimidazoles 6 are readily prepared from 1,2-diaminobenzenes 4 and 4,5-dichloro-1,2,3-dithiazolium chloride 1, either directly or through thermal or acid-catalysed rearrangement of the isolated imine intermediates 5; thermolysis of the imine 5b at 140-150°C simultaneously generates diatomic sulfur, S2, as shown by its interception.

Nucleophilic Substitution in Quaternary Salts of NN'-Linked Biazoles and Related Systems.

Some reactions of dicationic and monocationic N,N'-linked biazoles and of quaternized 1-(N-azolyl)pyridinium ions with nucleophiles have been studied.Although the pyrrolyl nucleus has been found to be a poor leaving group in these reactions, in other cases nucleophilic attack readily takes place at an azolyl carbon atom, with subsequent elimination of the N-substituent.The 1-methyl-3-(1-methyl-1,2,4-triazol-4-ylio)benzimidazolium dication (1) reacted at room temperature with ammonium, diethylamine, methoxyde, hydroxide, and cyanide ions, and with sodium borohydride, giving in all cases the corresponding 2-substituted benzimidazoles in good yield.In the case of the 2,4,6-trimethyl-1-(2-methylpyrazol-1-io)pyridinium dication (6), the reaction with cyanide ion afforded, regioselectively, 5-cyano-1-methylpyrazole, with no trace of the isomeric 3-cyano-1-methylpyrazole.The synthesis of the cations and dications from N-aminoazoles was easily performed.The reaction of 1-aminobenzimidazole with dehydroacetic acid in aqueous hydrochloric acid gave not only the expected 1-benzimidazol-1-yl-2,6-dimethylpyridin-4(1H)-one (9), but also 3-acetyl-1-benzimidazol-1-yl-4-hydroxy-6-methylpyridin-2(1H)-one (11).In pyridine, a pyran-2,4-dione intermediate (10), isomeric to (11), was also isolated.The quaternization reactions were easily performed, but high temperatures caused cleavage of the N-N bond.