3190-03-2

Upstream product

• 108-94-1 cyclohexanone 
• 95-54-5 1,2-diamino-benzene 
• 27429-80-7 spiro[2H-benzimidazole-2,1'-cyclohexane] 

Downstream Products

• 100381-49-5 1-(cyclohex-1-enyl)-1,3-dihydro-2H-benzimidazol-2-one 
• 100615-14-3 1-cyclohexyl-1,3-dihydro-2H-benzimidazol-2-one 
• 63953-62-8 5,6-bis-phenylsulfanyl-spiro[benzoimidazole-2,1'-cyclohexane] 
• 65023-38-3 5-benzenesulfonyl-1,3-dihydro-spiro[benzoimidazole-2,1'-cyclohexane] 
• 63953-64-0 5-phenylsulfanyl-6-piperidin-1-yl-spiro[benzoimidazole-2,1'-cyclohexane] 
• 65023-45-2 5-phenylsulphonyl-2H-benzimidazole-2-spirocyclohexane 
• 882-33-7 diphenyldisulfane 
• 117644-40-3 5-p-tolylsulphonyl-2H-benzimidazole-2-spirocyclohexane 
• 94526-35-9 N,N'-Bis-(5-benzenesulfonyl-spiro[benzoimidazole-2,1'-cyclohex]-4-yl)-hexane-1,6-diamine 
• 94526-34-8 N,N'-Bis-(5-benzenesulfonyl-spiro[benzoimidazole-2,1'-cyclohex]-4-yl)-ethane-1,2-diamine 
• 94526-58-6 5-phenylsulphonyl-4,6-bisphenylthioisobenzimidazole-2-spirocyclohexane 
• 94526-59-7 5-phenylsulphonyl-4,6-bis-t-butylthioisobenzimidazole-2-spirocyclohexane 
• 94526-31-5 5-Benzenesulfonyl-4-[(E)-2-(4-methyl-piperazin-1-yl)-vinyl]-spiro[benzoimidazole-2,1'-cyclohexane] 
• 94526-24-6 5-Benzenesulfonyl-4-(4-methyl-piperazin-1-yl)-spiro[benzoimidazole-2,1'-cyclohexane] 

Relevant academic research and scientific papers

Alumina supported 12-tungstophosphoric acid as an efficient and reusable catalyst for synthesis of 1,5-benzodiazepines

Alumina supported 12-tungstophosphoric acid catalyzes efficiently the reaction of o-phenylenediamine with ketones under solvent-free condition to afford the corresponding 1,5-benzodiazepines in good to excellent yields. The catalyst can be recovered and r

Electrochemical oxidation of o-phenylenediamine and 1,3 dihydrospiro[benzo[d]imidazole-2,1′-cyclohexane]. A comprehensive study and introducing a novel case of CE mechanism

Electrochemical behavior of o-phenylenediamine (PDA) and 1,3-dihydrospiro[benzo[d]imidazole-2,1′-cyclohexane] (DBI) was extensively studied in water and water/ethanol mixture using different voltammetric techniques. Our data showed that the oxidation of P

Reactions of fluoroalkyl-containing lithium 1,3-diketonates with diaminoarenes and 2-aminobenzenethiol

1,5-Benzo[b]- and 1,5-naphtho[2,3-b]diazepines were synthesized by the reaction of lithium 1,3-diketonates with 1,2-diaminobenzene and 2,3-diaminonaphthalene in an MeOH-AcOH-HCl mixture at 0°C. The reactions of fluoroalkyl-containing lithium 1,3-diketonates with 1,2-diaminobenzene and 1,2-diamino-4,5-difluorobenzene under reflux in acetic acid afford 2-fluoroalkyl-containing benzimidazoles as the major products, whereas the reaction with 2-aminothiophenol gives 2-phenylbenzothiazole. The reactions of lithium diketonate containing the cyclohexane and cyclopentane moieties with 1,2-diaminoarenes and 2-aminobenzenethiol are accompanied by the opening of the carbocycle to form 2-(6-oxo-7,7,7-trifluoroheptyl)benzimidazole and 2-(5-oxo-6,6,6-trifluorohexyl)benzothiazole hydrates, respectively.

Rearrangement of spiro-benzimidazolines: preparation of N-alkenyl- and N-alkyl-benzimidazol-2-ones

A synthetically useful protocol has been developed for the preparation of highly functionalized N-alkenyl-benzimidazol-2-ones. Reaction of commercially available o-phenylenediamines with variously substituted cyclic ketones provides spiro-benzimidazolines. Treatment of these spiro-benzimidazolines with triphosgene in the presence of potassium carbonate results in rapid rearrangement and formation of N-alkenyl-benzimidazol-2-ones in modest to excellent yield for the two-step sequence. Extension of this methodology toward the preparation of a μ opiate receptor antagonist and droperidol, a potent antiemetic and antipsychotic agent, currently a marketed pharmaceutical is also described. Upon treatment of spiro-benzimidazolines with triphosgene in the presence of sodium triacetoxyborohydride, N-alkyl-benzimidazol-2-ones were formed.