5622-83-3

Basic information

• Product Name: Pyrido[1,2-a]benzimidazole, 1,2,3,4-tetrahydro- (6CI,7CI,8CI,9CI)
• Synonyms: Pyrido[1,2-a]benzimidazole, 1,2,3,4-tetrahydro- (6CI,7CI,8CI,9CI)
• CAS NO: 5622-83-3
• Molecular Formula: C₁₁H₁₂N₂
• Molecular Weight: 172.23
• Product Categories: BENZIMIDAZOLE
• Mol File: 5622-83-3.mol

Chemical Properties

• Boiling Point: 472.2°C at 760 mmHg
• Flash Point: 239.4°C
• Appearance: /
• Density: 1.609g/cm³
• Vapor Pressure: 1.01E-09mmHg at 25°C
• Refractive Index: 1.805
• CAS DataBase Reference: Pyrido[1,2-a]benzimidazole, 1,2,3,4-tetrahydro- (6CI,7CI,8CI,9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Pyrido[1,2-a]benzimidazole, 1,2,3,4-tetrahydro- (6CI,7CI,8CI,9CI)(5622-83-3)
• EPA Substance Registry System: Pyrido[1,2-a]benzimidazole, 1,2,3,4-tetrahydro- (6CI,7CI,8CI,9CI)(5622-83-3)

Safety Data

• Hazardous Substances Data: 5622-83-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C18H11N3O4S/c19-9-13(6-11-4-5-16(22)17(23)7-11)18-20-15(10-26-18)12-2-1-3-14(8-12)21(24)25/h1-8,10,20,23H/b11-6+,18-13+

Upstream product

• 191542-44-6 1-<4-(phenylselanyl)butyl>-2-(phenylsulfanyl)-1H-benzimidazole 
• 22780-54-7 2-iminopiperidine 
• 615-42-9 1,2-Diiodobenzene 
• 710311-72-1 2-(4-chlorobutyl)-1H-benzo[d]imidazole 
• 95-54-5 1,2-diamino-benzene 
• 335645-39-1 2-(4-chlorobutyl)-2-ethoxy-1,3-dioxolane 
• 37859-43-1 2-chloromethylbenzothiazole 
• 1445-69-8 2,3-dihydrophthalazine-1,4-dione 
• 54624-57-6 2-bromo-1H-1,3-benzodiazole 
• 2453-51-2 4-(Benzimidazol-2-yl)-butan-1-ol 
• 542-28-9 3,4,5,6-tetrahydro-2H-pyran-2-one 
• 348-54-9 2-Fluoroaniline 
• 110-89-4 piperidine 
• 586-96-9 Nitrosobenzene 

Downstream Products

• 1343091-79-1 methyl-(2-piperidin-1-yl-phenyl)amine 
• 39643-31-7 2-piperidin-1-yl-phenylamine 
• 49809-51-0 2,3,4,5,6,7-hexahydro-1H-benzo[b][1,4]diazonine 

Relevant articles and documents

Switchable Regioselective 6-endo or 5-exo Radical Cyclization via Photoredox Catalysis

Controlling the regioselectivity of radical cyclizations to favor the 6-endo mode over its kinetically preferred 5-exo counterpart is difficult without introducing substrate prefunctionalization. To address this challenge, we have developed a simple method for reagent controlled regioselective radical cyclization of halogenated N-heterocycles onto pendant olefins. Radical generation occurs under mild photoredox conditions with control of the regioselectivity governed by the rate of hydrogen atom transfer (HAT). Utilizing a polarity-matched thiol-based HAT agent promotes the highly selective formation of the 5-exo cyclization product. Conversely, limiting the solubility of the HAT reagent Hantzsch ester (HEH) leads to selective formation of the thermodynamically favored 6-endo product. This occurs through an initial 5-exo cyclization, with the resulting alkyl radical intermediate undergoing neophyl rearrangement to form the 6-endo product. Development of this switchable catalysis strategy allows for two modes of divergent reactivity to form either the 6-endo or 5-exo product, generating fused N-heteroaromatic/saturated ring systems.

Electrochemical Synthesis of Benzo[ d]imidazole via Intramolecular C(sp3)-H Amination

An electrochemical dehydrogenative amination for the synthesis of benzimidazoles was developed. This electrosynthesis method could address the limitations of the C(sp3)-H intramolecular amination synthesis reaction and provide novel access to obtain 1,2-disubstituted benzimidazoles without transition metals and oxidants. Under undivided electrolytic conditions, various benzimidazole derivatives could be synthesized, exhibiting functional group tolerance.

Study of the Effect of Substituents of ortho-Phenylenediamines in the Opening of Lactones and Lactams for Access to Benzimidazol-2-yl Alkanols and Benzimidazol-2-yl Alkylamines

Benzimidazoles represent common chemical moieties in bioactive compounds. The synthesis of this heterocycle often involves a condensation of an ortho-phenylenediamine with a carboxylic acid derivative. The observed dialkylation of the starting ortho-phenylenediamine is avoided by opening of lactones or lactams. This strategy can directly yield 1 H-benzimidazoles substituted at the 2-position by a functionalized chain. We present herein a study of the effect of different electron-withdrawing or electron-donating groups at the 4-position of ortho-phenylenediamines on the opening of lactones or lactams to synthesize benzimidazol-2-yl alkanols and benzimidazol-2-yl alkylamines.

Electroreductive heterocyclization of ortho-piperidino substituted nitro(het)arenes

Electrochemical reduction of ortho-piperidino substituted nitro(het)arenes in an undivided cell on a lead cathode in 8% HCl gave either 1,2,3,4-tetrahydropyrido[1,2-a]-benzimidazoles or 6,7,8,9-tetrahydropyrido[3′,2′:4,5]- imidazo[1,2-a]pyridines. The red

Synthesis of rutaecarpine alkaloids: Via an electrochemical cross dehydrogenation coupling reaction

Substrates are directly oxidized at the anode without using any metal catalyst and oxidant to obtain a series of nitrogen heterocyclic compounds, including benzimidazoles and quinolinones. These compounds are highly tolerant to various functional groups and heterocycle-containing substrates. In addition, natural alkaloids, such as rutaecarpine and deoxyvasicinone, can be synthesized by this method.

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.

Copper-Catalyzed Double C-N Bond Formation for the Synthesis of Diverse Benzimidazoles from N -Alkyl-2-iodoaniline and Sodium Azide

An efficient approach to the synthesis of benzimidazole derivatives has been achieved by copper-catalyzed double C-N bonds formation of N-alkyl-2-iodoaniline and sodium azide. The reaction was supposed to proceed through copper-catalyzed tandem reaction of SNAr reaction, aerobic oxidation of C(sp3)-H bond and intramolecular C-N bond formation sequence. Structurally diverse 2-aryl, alkenyl and alkyl benzoimidazole derivatives were assembled by this methodology.

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.

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.