55536-69-1

Upstream product

• 58052-80-5 2,4,6-trimethyl-hexahydro-[1,3,5]triazine; trihydrate 
• 105-45-3 acetoacetic acid methyl ester 
• 14205-39-1 methyl (E)-3-aminocrotonate 
• 75-07-0 acetaldehyde 
• 631-61-8 ammonium acetate 
• 108-05-4 vinyl acetate 

Downstream Products

• 39273-88-6 dimethyl 2,4,6-trimethylpyridine-3,5-dicarboxylate 
• 27525-74-2 dimethyl 2,6-dimethylpyridine-3,5-dicarboxylate 

Relevant academic research and scientific papers

1,4-Dihydropyridines: discovery of minimal AIEEgens and their mitochondrial imaging applications

Typical aggregation-induced emission enhancement fluorogens (AIEEgens) generally are designed as propeller-shaped molecules with multiple aromatic rotors. Described herein are 1,4-dihydropyridines, which have the minimum size necessary for AIEE, containing only a single ring, synthesized through a facile biocatalysis procedure. Owing to the AIEE property, intramolecular motion can be restrained by the surrounding environment, causing the radiative channel to open up. Both the fluorescence intensities and the lifetimes of the 1,4-dihydropyridine representatives increased with increasing viscosity, and high sensitivities were observed. On the basis of the single crystal X-ray structures, density functional theory (DFT) calculations were performed to explain the mechanism of the single-ring AIEE behaviour. Moreover, a few of the neutral AIEEgens were found to possess a high specificity towards mitochondria. As an example, one of the AIEEgens exhibited superior photostability and excellent storage tolerance, allowing for real-time imaging, viscosity mapping, and long-term tracking of the dynamics of the mitochondrial morphology.

Alkyl transfer from C-C cleavage

Hydrogenation was only the beginning: Hantzsch esters have now been used to transfer alkyl groups to imines under mild catalytic conditions to provide a variety of amines (see scheme). Benzyl, secondary alkyl, and tertiary alkyl groups containing ether, ester, and hydroxy functionalities were transferred successfully. The use of Hantzsch esters as alkylation reagents offers a practical and complementary alternative to organometallic processes. Copyright

Laccase-catalyzed oxidation of Hantzsch 1,4-dihydropyridines to pyridines and a new one pot synthesis of pyridines

The laccase-catalyzed oxidation of 1,4-dihydropyridines to pyridines using aerial O2 as the oxidant exclusively delivers pyridines with yields up to 95% under mild reaction conditions. Combination of the Hantzsch 1,4-dihydropyridine synthesis with the newly developed laccase-catalyzed oxidation forms the basis of a facile and environmentally benign method for the synthesis of pyridines in one pot.

One-pot synthesis of hantzsch dihydropyridine catalyzed by ionic liquid (BmimOAc) and the oxidative aromatization of dihydropyridine using FeCl 3·6H2O

A series of 1,4-dihydropyridines were synthesized in one pot synthesis with the yield of 80-93 % using ionic liquid [bmim]OAc as catalyst and DMF as solvent. The ionic liquid could be repeatedly utilized 5 times with no decrease of the yield. The aromatization of these dihydropyridines (4a, 4b, 4d, 4f, 4h and 4i) were executed by the action of iron chloride and the post-processing was simplified using ethanol instead of water in dissolving dihydropyridines.

Bismuth trichloride - A clean, green catalyst for the synthesis of Hantzsch 1,4-dihydropyridines (DHPs)

Hantzsch 1,4-dihydropyridines (DHPs) are synthesized in good to excellent yields from aldehydes, 1,3-dicarbonyl compounds and ammonium acetate using bismuth trichloride which acts as mild Lewis acid promoter and 10 mol% is enough for this protocol under solvent free conditions.

Aromatization of hantzsch 1,4-dihydropyridines with Al(NO 3)39H2O and/or Fe(NO3)39H2O in the presence of silica sulfuric acid under mild and heterogeneous conditions

A simple and convenient method for the aromatization of Hantzsch 1,4-dihydropyridines to the corresponding pyridines is achieved via combination of aluminum or ferric nitrates and silica sulfuric acid as environmentally friendly and novel oxidizing media.

Gallium(III) chloride as an efficient new catalyst for the production of Hantzsch 1,4-dihydropyridines

Hantzsch 1,4-dihydropyridines (DHPs) are synthesized in good to excellent yields from aldehydes, 1,3-dicarbonyl compounds and ammonium acetate using gallium(III) chloride which acts as dehydrating agents and 5 mol% is enough for this protocol under solvent free conditions.

New efficient protocol for the production of hantzsch 1,4-dihydropyridines using RuCl3

Hantzsch 1,4-dihydropyridines are synthesized in a few minutes and in good to excellent yields from aldehydes, 1,3-dicarbonyl compounds, and ammonium acetate. The reaction is performed in solvent-free conditions, and 5mol% of RuCl3 is enough for this protocol.

Efficient synthesis of Hantzsch esters and polyhydroquinoline derivatives in aqueous micelles

Hantzsch 1,4-dihydropyridine and polyhydroquinoline derivatives were synthesized in excellent yields in aqueous micelles. The reaction is catalyzed by PTSA and strongly accelerated by ultrasonic irradiation. Georg Thieme Verlag Stuttgart.

Synthesis of Hantsch 1,4-dihydropyridines by fermenting bakers' yeast

Hantsch 1,4-dihydropyridines are prepared by fermenting bakers' yeast with alkyl acetoacetate and ammonium acetate.