83792-76-1

Usage

Synthesis Reference(s)

Tetrahedron Letters, 40, p. 1103, 1999 DOI: 10.1016/S0040-4039(98)02592-1

Upstream product

• 108-91-8 cyclohexylamine 
• 95-54-5 1,2-diamino-benzene 
• 1122-82-3 isothiocyanatocyclohexane 
• 583-39-1 2,3-dihydrobenzimidazol-2-thione 
• 98154-63-3 2-ethyl-1,2,4-thiadiazolo[4,5-a]benzimidazole-3(2H)-one 
• 4426-69-1 cyclohexyl isoselenocyanate 
• 934-32-7 1H-benzimidazol-2-amine 
• 108-93-0 cyclohexanol 
• 931-53-3 Cyclohexyl isocyanide 
• 87504-17-4 2-cyclohexylbenzimidazo<1,2-d><1,2,4>thiadiazol-3(2H)-one 
• 85997-29-1 2-butylbenzimidazo<1,2-d><1,2,4>thiadiazol-3(2H)-one 
• 72885-92-8 2-phenyl-2H-benzo[4,5]imidazo[1,2-d][1,2,4]thiadiazol-3-one 
• 221013-91-8 1-(2-aminophenyl)-3-cyclohexylthiourea 

Relevant academic research and scientific papers

Cobalt-Catalyzed Aerobic Oxidative Cyclization of 2-Aminoanilines with Isonitriles: Facile Access to 2-Aminobenzimidazoles

A ligand- and additive-free aerobic cobalt-catalyzed synthesis of 2-aminobenzimidazoles from 2-aminoanilines was developed. A variety of aminoanilines and isonitriles undergo efficient coupling to furnish substituted 2-aminobenzimidazoles in moderate to excellent yields. This protocol enables efficient access to the unsubstituted 2-aminobenzimidazoles.

Cobalt-catalyzed oxidative isocyanide insertion to amine-based bisnucleophiles: Diverse synthesis of substituted 2-aminobenzimidazoles, 2-aminobenzothiazoles, and 2-aminobenzoxazoles

Cobalt catalysis: Synthesis of substituted 2-aminobenzimidazoles, 2-aminobenzothiazoles, and 2-aminobenzoxazoles was achieved by using cobalt(II) acetate catalyzed isocyanide insertion to o-diaminobenzene, 2-aminobenzenethiol, and 2-aminophenol derivatives in 1,4-dioxane (see scheme). It was found that the reaction proceeded efficiently to give the desired products in up to 95 % isolated yields by C-N and C-S (O, N) formation in a single step. Copyright

Regioselective N-alkylation of 2-aminoimidazoles with alcohols to 2-(N-Alkylamino)imidazoles catalyzed by the [Cp*IrCl2] 2/K2CO3 system

The direct N-alkylation of 2-aminoimidazoles to give the corresponding 2-(N-alkylamino)imidazoles was accomplished using alcohols as alkylating agents in the presence of a [Cp*IrCl2]2/K 2CO3 system. The iridium-catalyzed regioselective reaction is simple, efficient, general, and environmentally benign. The direct N-alkylation of 2-aminoimidazoles to give the corresponding 2-(N-alkylamino) imidazoles was accomplished using alcohols as alkylating agents in the presence of a [Cp*IrCl2]2/K2CO3 system. The iridium-catalyzed regioselective reaction is simple, efficient, general, and environmentally benign. Copyright

Phosphonium-mediated cyclization of N-(2-aminophenyl)thioureas: Efficient synthesis of 2-aminobenzimidazoles

BOP efficiently promoted the phosphonium-mediated cyclization of thioureas, leading to a convenient synthesis of 2-aminobenzimidazoles. Compared to conventional methods, the reactions were complete at room temperature with times ranging from a few minutes

Novel synthesis of 2-aminobenzimidazoles from isoselenocyanates

An efficient one-pot procedure for the synthesis of 2-aminobenzimidazoles from isoselenocyanates and various substituted diamines is described. Precipitation of elemental selenium from the reaction mixture greatly simplifies the purification procedure and also allows it to be re-used for preparation of isoseleno?cyanates. A possible mechanism for the formation of 2-aminobenzimidazoles is proposed. Georg Thieme Verlag Stuttgart - New York.

A convenient method for the synthesis of 2-amino substituted aza-heterocycles from N,N′-disubstituted thioureas using TsCl/NaOH

p-Toluenesulfonyl chloride (TsCl)/NaOH has been introduced as reagent combination for the synthesis of 2-amino-oxa- or 2-amino-thiazolidines from N-(2-hydroxyethyl)-thioureas, but its general application in heterocycle synthesis has not been investigated. In this paper the convenient and efficient synthesis of a variety of 2-amino-substituted 1-aza 3-(aza, oxo or thio) heterocycles of different substitution and ring sizes is described. The application of polymer-supported TsCl facilitates work-up and renders the reaction conditions very suitable for parallel or robot synthesis. Graphical Abstract

Synthesis of 2-(alkylamino)benzimidazoles

A general and highly convenient procedure for the synthesis of 2- (alkylamino)benzimidazoles has been developed and a variety of analogs have been efficiently prepared. Included is a dipeptide mimetic in which the guanidine group of an arginine residue ha

Fission of 1,2,4-Thiadiazol-3-ones by Triphenylphosphane: Triphenylphosphonio Thioimidazolates and Their Consecutive Reactions

Treatment of benzimidazothiadiazol-3(2H)-ones (1) and imidazothiadiazol-3(2H)-ones (17) with triphenylphosphan leads to the liberation of isocyanate and the formation of triphenylphosphonio-thiobenzimidazolat (4) and triphenylphosphonio-thioimidazolat (18), respectively. 2,4-Diphenyl-5-phenylimino-1,2,4-thiadiazol-3-one (23) is desulfurized with Ph3P and decomposed into phenyl isocyanate and diphenylcarbodiimide whereas the N-unsubstituted imino-thiadiazol-3-one (25) is attacked at the exocyclic imino group by Ph3P to give the N-phosphoranylidene thiourea (26).The structure of 4 can be rationalized as a dynamic system between polar and apolar valence isomeres.Reactions of 1 and 17 with cyanates, isocyanates, carbon disulfide, acetic anhydride, amines, benzyl chloride, grignard compounds, and CH acidic compounds are described.