34551-62-7

Usage

Chemical class

Dihydropyridine derivatives

Physical state

Yellow crystalline solid

Molecular weight

354.4 g/mol

Pharmaceutical use

Research and drug development, particularly in calcium channel blockers

Therapeutic applications

Antihypertensive, anti-anginal, and antiarrhythmic agents

Chemical property

Presence of a nitro group, which may contribute to its pharmacological activity

Further research

Needed to fully understand potential applications and properties

Upstream product

• 99-61-6 3-nitro-benzaldehyde 
• 123-54-6 acetylacetone 
• 34551-63-8 (2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-diyl)diethanone 
• 1118-66-7 4-Aminopent-3-en-2-one 
• 60-35-5 acetamide 
• 21829-28-7 2,6-dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester 
• 506-87-6 ammonium carbonate 
• 552-89-6 2-nitro-benzaldehyde 

Downstream Products

• 99286-83-6 1-[(2R,3S,4R)-5-Acetyl-2,6-dimethyl-4-(3-nitro-phenyl)-1,2,3,4-tetrahydro-pyridin-3-yl]-ethanone 
• 99286-88-1 1-[(2R,3S,4S,5R,6S)-5-Acetyl-2,6-dimethyl-4-(3-nitro-phenyl)-piperidin-3-yl]-ethanone 

Relevant academic research and scientific papers

A Simple and Efficient One-pot Synthesis of 1,4-dihydropyridines Using Nano-WO3-supported Sulfonic Acid as an Heterogeneous Catalyst under Solvent-free Conditions

Nano-tungsten trioxide-supported sulfonic acid (n-WSA) was found to be an effective heterogeneous catalyst for the one-pot reaction of aromatic aldehydes, β-dicarbonyl compounds and ammonium acetate to afford 1,4-dihydropyridine derivatives in good to excellent yields. The other main advantages of the present method are short reaction times, simple workup, ease in purification and environmentally benign methodology. The reaction conditions were optimized employing Response Surface Method technique (Central Composite Design (CCD)) which is economically considerable because of the minimum number of experiments required to evaluate the effects of multiple parameters on the response.

Solvent-free efficient one-pot synthesis of Biginelli and Hantzsch compounds catalyzed by potassium phthalimide as a green and reusable organocatalyst

The usage of potassium phthalimide (PPI) for the simple and green one-step multicomponent synthesis of Hantzsch 1,4-dihydropyridines, polyhydroquinolines, 3,4-dihydropyrimidin-2(1H)-ones/thiones, and octahydroquinazolinones under solventless conditions at 120°C is reported. The method is operationally simple, environmentally benign, and has relatively high yields. The other merits of this method include efficient, clean, green, and catalyst reusability.

Ultrasound-mediated, uranyl nitrate hexahydrate-catalyzed synthesis of 1,4-dihydropyridines under mild conditions

Abstract Synthesis of 1,4-dihydropyridines by three-component condensation reaction of aldehyde, 1,3-dicarbonyl compounds, and ammonium acetate have been found to be efficiently catalyzed by uranyl nitrate hexahydrate [UO2(NO3)2 ·6H2O] at room temperature under ultrasound irradiation. This novel synthetic method offers the advantages of high yields, short reaction times, simplicity, and easy workup compared to the conventional methods reported in the literature.

Synthesis and 3D-QSAR study of 1,4-dihydropyridine derivatives as MDR cancer reverters

A series of symmetrical and unsymmetrical 1,4-dihydropyridines were synthesized by a rapid, single pot microwave irradiation (MWI) based protocol along with conventional approach and characterized by NMR, IR and mass spectroscopic techniques. The compound

Candida antarctica lipase B-catalyzed the unprecedented three-component Hantzsch-type reaction of aldehyde with acetamide and 1,3-dicarbonyl compounds in non-aqueous solvent

A direct approach to 1,4-dihydropyridines by lipase-catalyzed unprecedented three-component Hantzschtype reaction of aldehyde with 1,3-dicarbonyl compounds and acetamide in non-aqueous solvent has been developed. Some control experiments have been perform

Etidronic acid catalyzed synthesis of 1,4-dihydropyridines

One pot, three components cyclocondensation reaction of various arylaldehydes, ethyl acetoacetate/acetyl acetone and ammonium acetate with etidronic acid as catalyst afforded the corresponding 1,4-dihydropyridines in better yields under solvent free conditions.

Ionic liquid [EMIM]OAc under ultrasonic irradiation towards synthesis of 1,4-DHP's

The ionic liquid 1-ethyl-3-methylimidazole acetate ([EMIM]OAc) was found to be a mild and effective catalyst for the efficient, one-pot, three-component synthesis of 1,4-dihydropyridines from arylalde-hydes, ethylacetoacetate/ acetylacetone and ammonium acetate at room temperature under sonication. The developed method has many advantages, including devoid of harmful catalysts, reacting at room temperature, higher yields in a simple methodology or operational convenience.

Etidronic acid catalyzed synthesis of 1,4-dihydropyridines

One pot, three components cyclaconctensation reaction of various arylaldehydes. ethyl acetoacetate/acetyl acetone and ammonium acetate with etidronic acid as catalyst afforded the corresponding 1,4 -dihydropyridines in better yields under solvent free conditions.

Rapid and cleaner synthesis of 1,4-dihydropyridines in aqueous medium

The present investigation deals with a novel water soluble Lewis acid complex, Zn[(L)proline]2 catalyzed Hantzsch 1,4-dihydropyridine derivatives syntheses in aqueous medium assisted by microwave irradiation. The microwave promoted syntheses in aqueous medium afforded moderate to excellent yield (up to 98%) within short reaction time and allowed the reaction to take place with low microwave power (200 W). This synthetic methodology provides easier separation of products and the catalyst exhibits recycling ability without loss of its catalytic activity up to five reaction cycles.