79613-20-0

Upstream product

• 4414-88-4 1H-benzimidazol-2-acetonitrile 
• 123-11-5 4-methoxy-benzaldehyde 
• 154198-90-0 (E)-3-p-anisyl-2-cyano-2-propenoyl azide 
• 95-54-5 1,2-diamino-benzene 
• 27888-23-9 (E)-3-p-anisyl-2-cyano-2-propenoyl chloride 
• 2826-26-8 2-(4-methoxyphenylmethylene)malononitrile 

Downstream Products

• 2620-81-7 2-(4-methoxyphenyl)-1H-benzimidazole 
• 105508-19-8 2-Acetyl-3-(4-methoxy-phenyl)-1-oxo-1,2-dihydro-benzo[4,5]imidazo[1,2-a]pyridine-4-carbonitrile 
• 105508-22-3 1-Amino-4-cyano-3-(4-methoxy-phenyl)-benzo[4,5]imidazo[1,2-a]pyridine-2-carboxylic acid hydrazide 

Relevant academic research and scientific papers

Magnetic nanoparticle supported amine: An efficient and environmental benign catalyst for versatile Knoevenagel condensation under ultrasound irradiation

Amine functionalized silica coated Fe3O4 nanoparticles (SiO2@MNP-A) were successfully prepared as a novel heterogeneous amine. The catalyst was characterized by XRD, FT-IR, TEM, magnetic measurement, elemental analysis and was found to be a magnetically separable and highly active catalyst for ambient Knoevenagel condensation of aromatic aldehydes and a-aromatic (heteroaromatic or polyaromatic)-substituted methylene compounds in water under ultrasonic irradiation to afford the corresponding products in good to excellent yields. Very interestingly, SiO2@MNP-A successfully catalyze the reaction of the non-cyano substituted compound with benzaldehyde to achieve a key intermediate for the preparation of Atorvastatin calcium in green and atom-economic manner. In addition, the catalyst SiO2@MNP-A can be reused for 8 times without any obvious loss of its activity. The role of ultrasonication in the Knoevenagel condensation was also discussed with the assistance of UV-vis spectrometry.

Knoevenagel condensation reaction using ionic liquid [ADPQ][CF3SO3] as green and reusable catalyst

Knoevenagel condensation reaction of aromatic aldehydes with some active methylene compounds proceeded efficiently without solvent using ionic liquids as catalyst. The experimental results show that these ionic liquids have good catalytic activities to th

Synthesis, x-ray crystal structures, stabilities, and in vitro cytotoxic activities of new heteroarylacrylonitriles

Twenty-three acrylonitriles, substituted at position 2 with either triazoles or benzimidazoles and at position 3 with various substituted furan, thiophene, or phenyl rings, were prepared by Knoevenagel condensation and tested for in vitro cytotoxic potency on 11 human cancer cell lines. X-ray crystal analysis of two representative compounds showed that the olfenic bond is E-configured. Structure-activity-relationships (SAR) indicated that position 2 is flexible for substituents with various nitrogen heterocyclics while position 3 is very sensitive to change; the most potent compounds contained a 5-nitrothiophen-2-yl ring at position 3 and either benzimidazol-2-yl (11) or a 5-benzyl-1H-[1,2,4]-triazol-3-yl (7) group at position 2 of acrylonitrile. SARs for the thiophen-2-yl-benzimidazoles show the following trend for position 5: NO2 ? H > Cl = CH3. Compound 11 was on average 10- and 3-fold more potent than cisplatin and etoposide, respectively. However, the acrylonitrile functionality is not an absolute requirement for cytotoxic activity because replacement of the nitrile group for either a hydrogen or a methyl group also gave active compounds. The acrylonitriles caused delayed cell death characterized by giant cells with multilobed nuclei. Compound 11 was found to bring about the increase in the activities of caspases 3 and 9 in the HL-60 cell line in a manner similar to etoposide, strongly indicating that apoptosis is the mechanism of cell death. The selectivity of various compounds toward cancer cells was estimated by comparing the IC50 values obtained from a noncancerous epithelial cell line, h-TERT-RPE1, with the average IC50 value from the cancer cell lines; 11 showed an average 1.7-fold greater activity toward cancer cells. The stabilities of the new compounds under cell culture conditions, estimated by HPLC, indicated that a major fraction of the compounds were lost from the medium over the first 24 h.

Synthesis and insecticidal activity of novel acrylonitrile derivatives

(E)-3-p-Anisyl-2-cyano-2-propenoyl chloride and/or azide (1b and c) underwent successful nucleophilic displacement reactions, with urea and thiourea derivatives to give the mono-or di-displacement products (4, 8, 2 and 5) respectively, beside other cyclic

Synthesis of Polyazaheterocycles by Michael Addition of CH Acids to α,β-Unsaturated Nitriles. Synthesis of Pyridobenzimidazole and Pyrimidopyridobenzimidazole Derivatives

Addition of 1H-benzimidazole-2-carbonitrile (1) to arylidenemalononitrile (2) gave 1-amino-3-aryl pyridobenzimidazole-2,4-dicarbonitrile (3), 2-aryl-benzimidazole (4) and 1H-benzimidazole-2-acetonitrile, α-(arylmethylene) (5).Compounds (3) reacted with formamide yielding 4-amino-5-aryl pyrimidopyridobenzimidazole (6).