89101-27-9

Upstream product

• 51-17-2 benzoimidazole 
• 3282-32-4 2-diazo-acetophenone 
• 70-11-1 α-bromoacetophenone 
• 2142-69-0 2-bromophenyl methyl ketone 
• 2849-93-6 2-benzimidazolecarboxylic acid 
• 5805-53-8 BICA methyl ester 
• 532-27-4 1-chloroacetophenone 
• 100-42-5 styrene 
• 93-91-4 1-phenylbutan-1,3-dione 

Downstream Products

• 34572-26-4 2-(1H-benzimidazol-1-yl)-1-phenylethanol 
• 442160-79-4 (E)-2-Benzoimidazol-1-yl-3-dimethylamino-1-phenyl-propenone 
• 1226569-91-0 C₂₁H₁₈N₄ 

Relevant academic research and scientific papers

Synthesis and structural analysis of complexes based on α-amino ketone derived from benzimidazole

Two cobalt (II) and nickel (II) coordination compounds have been synthesized starting from 2-(1H-benzimidazol-1-yl)-1-phenylethanone, an α-amino ketone with the N atom belonging to an imidazole ring. The newly synthesized compounds have been characterized by spectral methods (IR, UV-Vis-NIR), thermal analysis, magnetic data and single-crystal X-ray diffraction. The single-crystal X-ray structure of the cobalt (II) complex shows a tetragonal octahedral geometry with four organic ligands in the equatorial plane and two nitrate ions in the axial positions. An interesting feature is the dynamic disordering of the distortions inside the coordination units, due to one intra-molecular hydrogen bond traveling between one nitrate axial ligand and each of the four organic ligands. The electronic structure calculations, in the frame of Density Functional Theory (DFT), are sustaining this hypothesis, revealing optimized molecular geometries less symmetrical than the experimental shape, which is an average over equivalent distortions. The modeled reaction coordinate gave a shallow barrier, 2.36 kcal/mol, for the transformation between the four equivalent geometries corresponding to the intramolecular floppy hydrogen bonding. Entering methodological issues, we showed that the Time Dependent (TD) routines for computing electronic spectra in the DFT frame cannot account completely for ligand field driven d-d transitions. However, with dedicated analysis, useful information on the ligand field scheme can be extracted.

Synthesis of 3-Phenyl-1H-[1,4]oxazino[4,3-a]benzimidazol-1-one and Its Transformation into 4-Phenyl-2,5-dihydro-1H-[1,2,5]triazepino[5,4-a]benzimidazol-1-one

Abstract: A synthetic route has been proposed to 3-phenyl-1H-[1,4]oxazino[4,3-a]benzimidazol-1-one, which is the first representative of a new heterocyclic system. The transformation of the title compound to 4-phenyl-2,5-dihydro-1H-[1,2,5]triazepino[5,4-a]benzimidazol-1-one via reaction with hydrazine hydrate has been studied.

N - alkyne base benzene and preparation method for imidazole derivatives (by machine translation)

The invention discloses a preparation method of N-alkynyl benzimidazole derivatives, which comprises the following step: under the atmosphere of protective gas, sequentially adding LiHMDS, diethyl chlorophosphate and LiHMDS into an anhydrous solvent of 1-R1 formyl-methyl 2-R2 benzimidazole as shown in the general formula 2 so as to react to obtain an N-alkynyl benzimidazole derivative as shown in the general formula 1, wherein when LiHMDS is added for reacting, the temperature is controlled at -78-0 DEG C, and after ClP(O)(OEt)2 is added, the system temperature rises to 10-30 DEG C so as to react. The preparation method of the N-alkynyl benzimidazole derivatives has the advantages that (1) substrates can be conveniently prepared through cheap raw materials; (2) the universality is good, and preparation of benzimidazole alkyne amine derivatives containing different substituent combinations can be easily realized; (3) the operation is simple and convenient, and the separation of intermediates is not needed; and (4) target compounds are easy to separate and purify, and the yield is relatively high.

A METAL FREE PROCESS FOR THE PREPARATION OF ALPHA-SUBSTITUTED CARBONYL COMPOUNDS FROM ALKENES

The present invention discloses a novel metal free process for the regioselective synthesis of α-substituted carbonyl compounds of formula I from alkene, X is selected from the following compounds (A, B).

Regioselective oxo-amination of alkenes and enol ethers with N-bromosuccinimide-dimethyl sulfoxide combination: A facile synthesis of α-amino-ketones and esters

An unprecedented conversion of alkenes and enol ethers to the corresponding α-imido carbonyl compounds with excellent regioselectivity and yields has been developed. This oxo-amination process employs readily available N-bromosuccinimide (NBS) and secondary amines as N-sources and dimethyl sulfoxide (DMSO) as the oxidant and also leads to the production of amino alcohols in a single step on reduction, thus broadening the scope of this operationally simple reaction. For the first time, the formation of reactive Me2S+-O-Br species generated by the interaction of NBS with DMSO has been proven.

A facile protocol for N-alkylation of azoles using KOtBu as base under NBS-promoted conditions

A mild, transition metal-free, and environmentally benign NBS-promoted C-N bond formation of N-heterocycles is successfully demonstrated. A series of heterocyclic derivatives are readily prepared under mild conditions in moderate to good yields.

Design and synthesis of some novel oxiconazole-like carboacyclic nucleoside analogues, as potential chemotherapeutic agents

The syntheses of some novel carboacyclic nucleosides, 17a-17o, containing oxiconazole-like scaffolds, are described (Schemes 1-3). In this series of carboacyclic nucleosides, pyrimidine as well as purine and other imidazole derivatives were employed as an imidazole successor in oxiconazole. These compounds could be prepared in good yields by using two different strategies (Schemes 1 and 2). Due to Scheme 1, the N-coupling of nucleobases with 2-bromoacetophenones was attained for 18a-18e, and their subsequent oximation affording 19a-19e and finally O-alkylation with diverse alkylating sources resulted in the products 17a-17g, 17n, and 17o. In Scheme 2, use of 2-bromoacetophenone oximes 20, followed by N-coupling of nucleobases, provided 19f-19j whose final O-alkylation produced 17h-17m (Scheme 2). For the rational interpretation of the dominant formation of (E)-oxime ethers rather than (Z)-oxime isomers, PM3 semiempirical quantum-mechanic calculations were discussed and the calculations indicated a lower heat of formation for (E)-isomers.

REGIOSELECTIVE N-ALKYLATION OF BENZIMIDAZOLE VIA AN ORGANOTIN ROUTE

A simple and efficient method for the exclusive N-alkylation of benzimidazole with functional group compatibility has been achieved.