19979-46-5

Basic information

• Product Name: 6H-Azepino[1,2-a]benzimidazole,7,8,9,10-tetrahydro-(7CI,8CI,9CI)
• Synonyms: 6H-Azepino[1,2-a]benzimidazole,7,8,9,10-tetrahydro-(7CI,8CI,9CI)
• CAS NO: 19979-46-5
• Molecular Formula: C₁₂H₁₄N₂
• Molecular Weight: 186.25296
• Product Categories: BENZIMIDAZOLE
• Mol File: 19979-46-5.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 6H-Azepino[1,2-a]benzimidazole,7,8,9,10-tetrahydro-(7CI,8CI,9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 6H-Azepino[1,2-a]benzimidazole,7,8,9,10-tetrahydro-(7CI,8CI,9CI)(19979-46-5)
• EPA Substance Registry System: 6H-Azepino[1,2-a]benzimidazole,7,8,9,10-tetrahydro-(7CI,8CI,9CI)(19979-46-5)

Safety Data

• Hazardous Substances Data: 19979-46-5(Hazardous Substances Data)

Upstream product

• 201230-82-2 carbon monoxide 
• 134856-37-4 N-(pent-4-enyl)benzene-1,2-diamine 
• 51-17-2 benzoimidazole 
• 111-24-0 1,5-dibromo-pentane 
• 88-73-3 2-Chloronitrobenzene 
• 105-60-2 caprolactam 
• 615-36-1 2-bromoaniline 
• 1370281-21-2 N-[azepan-2-ylidene]-2-bromoaniline 
• 63086-94-2 spiro[2H-benzimidazole-2,1'-cyclohexane]-1-oxide 
• 31983-86-5 spiro[2H-benzimidazole-2,1'-cyclohexane]-1,3-dioxide 
• 1426222-10-7 methyl 6-(1H-benzimidazol-1-yl)hexanoate 
• 1426221-93-3 6-(1H-benzimidazol-1-yl)hexanoic acid 
• 14273-90-6 methyl 6-bromohexanoate 
• 51627-46-4 2-(azepan-1-yl)aniline 

Relevant articles and documents

Metal-Free Sequential C(sp2)-H/OH and C(sp3)-H Aminations of Nitrosoarenes and N-Heterocycles to Ring-Fused Imidazoles

Hydrogen bond assisted ortho-selective C(sp2)-H amination of nitrosoarenes and subsequent α-C(sp3)-H functionalization of aliphatic amines is achieved under metal-free conditions. The annulation of nitrosoarenes and 2-hydroxy-C-nitroso compounds with N-heterocycles provides a facile excess to a wide range of biologically relevant ring-fused benzimidazoles and structurally novel polycyclic imidazoles, respectively. Nucleophilic aromatic hydrogen substitution (SNArH) was found to be preferred over classical SNAr reaction during the C(sp2)-H amination of halogenated nitrosoarenes.

Formic acid as a sustainable and complementary reductant: An approach to fused benzimidazoles by molecular iodine-catalyzed reductive redox cyclization of: O -nitro- t -anilines

Molecular iodine was found to be an excellent catalyst for reductive redox cyclization of o-nitro-t-anilines 1 into fused tricyclic or 1,2-disubtituted benzimidazoles 2. A range of functional groups such as halides (F, Cl, Br), methoxy, ester, trifluoromethyl, cyano, pyridine and even nitro groups were tolerated using formic acid as a clean, safe, user-friendly and complementary reductant. When iodine was used in a stoichiometric amount (50 mol%), the methodology allowed the direct synthesis of benzimidazole hydroiodides 2·HI in high yields by simple precipitation from the reaction mixture.

Synthesis of benzimidazoles via iridium-catalyzed acceptorless dehydrogenative coupling

Iridium-catalyzed acceptorless dehydrogenative coupling of tertiary amines and arylamines has been developed. A number of benzimidazoles were prepared in good yields. An iridium-mediated C-H activation mechanism is suggested. This finding represents a novel strategy for the synthesis of benzimidazoles.

Barton esters for initiator-free radical cyclisation with heteroaromatic substitution

S-(1-Oxido-2-pyridinyl)-1,1,3,3-tetramethylthiouronium hexafluorophosphate (HOTT) facilitates the first examples of efficient radical cyclisation with (hetero)aromatic substitution via Barton ester intermediates. Cyclopropyl and alkyl radicals allow acces

Synthesis of annulated benzimidazoles via amidine cyclization

Structurally diverse annulated benzimidazoles were synthesized via two copper(I)-catalyzed cyclocondensation reactions. In the first case the title compounds were prepared from lactams and o-bromoaniline. An alternative route consisted of an intramolecular cyclization of o-bromoarylamidines.

Thermal transformations of 2H-benzimidazole 1,3-dioxides

Thermal transformations of 2H-benzimidazole 1,3-dioxides represented by spiro[2H-benz-imidazole-2,1′-cyclohexane] 1,3-dioxide and its 5-nitro derivative were studied. Their heating resulted in reversible isomerization to spiro[3H-[2,1,4]benzoxadiazine-3,1

Aromatic homolytic substitution using solid phase synthesis

Solid phase synthesis has been used to carry out intramolecular aromatic homolytic substitution with benzoimidazole precursors. The protocol attaches the radical precursors to the resins via the radical leaving groups (in the aromatic homolytic substitution). When the radical reactions are complete, the leaving group, unaltered starting material and reduced uncylised products remain attached to the resin, which facilitates easy separation of the cyclised products. Novel use of focussed microwave irradiation in solid phase radical reactions drastically shortens the reactions times. Tributylgermanium hydride has been used to replace the toxic and troublesome tributyltin hydride in the radical reactions.

Synthesis of annelated imidazoles and benzimidazoles

A variety of fused ring imidazole or benzimidazole derivatives were prepared through two successive condensations of a dihalide with 4,5- diphenylimidazole or benzimidazole. The 2-methyl substituted derivatives of 4,5-diphenylimidazole or benzimidazole were also used. The size of the annelated ring, which is dependent on the dihalide used, can be varied from five to seven atoms. Initially, N-alkylhalo derivatives were prepared by condensation of the heterocyclic starting materials with a dihalide. Ring closure was then effected through intramolecular condensation of a carbanion derived from the 2-position or the 2-methyl group of the parent heterocyclic ring with the N-alkylhalo moiety.

Radical cyclisation onto imidazoles and benzimidazoles

New synthetic methodology has been developed for the synthesis of [1,2- a]fused imidazoles and benzimidazoles using intramolecular homolytic aromatic substitution. In the intramolecular substitution, N-(ω-alkyl) radicals are generated using Bu3SnH from N-(ω-phenylselanyl)alkyl side chains. Phenylselanyl groups are used as radical leaving groups to avoid problems in the N-alkylation of imidazoles and benzimidazoles. Arylsulfones for imidazoles, and phenylsulfides for benzimidazoles, are used at the leaving groups in the homolytic substitutions.

Radical cyclisation onto imidazoles and benzimidazoles

A new protocol for the synthesis of [1,2-a]-fused benzimidazoles and imidazoles has been developed using intramolecular homolytic aromatic substitution via ω-alkyl radicals generated from 1-(ω-benzeneselenylakyl)-2(benzenesulfenyl)- benzimidazoles and -2-(p-toluenesulfonyl)imidazoles.