71908-66-2

Upstream product

• 98-86-2 acetophenone 
• 109-77-3 malononitrile 
• 5447-87-0 2-(1-phenylethylidene)propanedinitrile 

Downstream Products

• 1228010-41-0 2-methyl-2,4-diphenyl-3,8-dihydro-2H-pyrazolo[3,4-h][1,6]naphthyridine-5,9-diamine 
• 1228010-37-4 2-(3-cyano-6-methyl-4,6-diphenyl-5-(2-phenylhydrazono)-5,6-dihydropyridin-2(1H)-ylidene)-malononitrile 
• 1228010-42-1 2-methyl-2,4,8-triphenyl-3,8-dihydro-2H-pyrazolo[3,4-h][1,6]naphthyridine-5,9-diamine 
• 1228010-39-6 2-[3-cyano-6-methyl-4,6-diphenyl-5-(2-(4-tolyl-hydrazono))-5,6-dihydropyridin-2(1H)-ylidene]-malononitrile 
• 1228010-38-5 2-(5-(2-(4-chlorophenyl)-hydrazono)-3-cyano-6-methyl-4,6-diphenyl-5,6-dihydropyridin-2(1H)-ylidene)-malononitrile 
• 1228010-40-9 2-[3-cyano-6-methyl-4,6-diphenyl-5-(2-(4-methoxyphenyl)-hydrazono)-5,6-dihydropyridin-2(1H)-ylidene]-malononitrile 
• 1449764-13-9 C₂₅H₂₃N₃O 
• 1449764-02-6 C₂₃H₁₉N₃O 
• 1449764-15-1 C₂₂H₁₉N₅ 

Relevant academic research and scientific papers

Synthetic dihydropyridines as novel antiacanthamoebic agents

Background: Acanthamoeba is an opportunistic pathogen widely spread in the envi-ronment. Acanthamoeba causes excruciating keratitis which can lead to blindness. The lack of ef-fective drugs and its ability to form highly resistant cyst are one of the foremost limitations against successful prognosis. Current treatment involves mixture of drugs at high doses but still recurrence of infection can occur due to ineffectiveness of drugs against the cyst form. Pyridine and its natural and synthetic derivatives are potential chemotherapeutic agents due to their diverse biological ac-tivities. Objective: To study the antiamoebic effects of four novel synthetic dihydropyridine (DHP) compounds against Acanthamoeba castellanii belonging to the T4 genotype. Furthermore, to evaluate their activity against amoeba-mediated host cells cytopathogenicity as well as their cytotoxicity against human cells. Method: Dihydropyridines were synthesized by cyclic dimerization of alkylidene malononitrile derivatives. Four analogues of functionally diverse DHPs were tested against Acanthamoeba castellanii by using amoebicidal, encystation and excystation assays. Moreover, Lactate dehydro-genase assays were carried out to study cytopathogenicity and cytotoxicity against human cells. Results: These compounds showed significant amoebicidal and cysticidal effects at 50 μM con-centration, whereas, two of the DHP derivatives also significantly reduced Acanthamoeba-mediated host cell cytotoxicity. Moreover, these DHPs were found to have low cytotoxicity against human cells suggesting a good safety profile. Conclusion: The results suggest that DHPs have potential against Acanthamoeba especially against the more resistant cyst stage and can be assessed further for drug development.

Dialkylated Dihydroazulene and Vinylheptafulvene Derivatives – Synthesis and Switching Properties

Functionalization of molecular photoswitches at specific positions offers a way of tuning their switching properties. The work presented here describes the development of a new protocol towards the synthesis and functionalization of the dihydroazulene/vinylheptafulvene (DHA/VHF) photo-/thermoswitch. The key step is a facile condensation reaction using a functionalized tropone derivative, and the new synthetic method was employed in the regioselective preparation of a novel dimethyl-substituted DHA photoswitch. This compound presents the first accessible derivative with alkyl groups on the seven-membered ring of the system ― at positions C5 and C7. From experimental and theoretical kinetics studies on the thermal VHF-to-DHA electrocyclic reaction, the influence of the electron-donating methyl groups was elucidated. In addition, we subjected a small selection of 4,8a-dialkylated compounds to a computational study to elucidate how steric interactions can alter the relative DHA–VHF stabilities. The synthetic methodology offers access to novel DHA scaffolds and substitution patterns, which in turn can lead to systems that can help to address broader questions concerning the potential applicability of the DHA/VHF system in the context of solar-thermal energy-storage systems or other photochromic applications.

One-pot synthesis of tetrazole-1,2,5,6-tetrahydronicotinonitriles and cholinesterase inhibition: Probing the plausible reaction mechanism via computational studies

In the present study, one-pot synthesis of 1H-tetrazole linked 1,2,5,6-tetrahydronicotinonitriles under solvent-free conditions have been carried out in the presence of tetra-n-butyl ammonium fluoride trihydrated (TBAF) as catalyst and solvent. Computatio

Pseudo-five-component domino strategy for the combinatorial library synthesis of [1,6] naphthyridines - An on-water approach

This work features the base-promoted on-water synthesis of [1,6]-naphthyridines from methyl ketones, malononitrile and phenols or thiols. The reaction conditions were carefully tuned to drive the product selectivity from 3H-pyrroles to [1,6]-naphthyridines. The advantages of this method lie in its simplicity, cost effectiveness, and environmental friendliness, representing a new effort toward the on-water synthesis of [1,6]-naphthyridines without starting from a nitrogen-containing heterocycle and highlighting the versatility of the nitrile functional group.

Synthesis of some novel polyaza fused heterocyclic compounds

(Chemical Equation Presented) 2-(1-Aryl-ethylidene)-malononitriles 1a-d undergo self dimerization in ethanol catalyzed by sodium ethoxide to afford 2-[4,6-diaryl-3-cyano-6-methyl-5,6-dihydropyridin-2(1H)-ylidene]-malononitrile derivatives 3a-d, respectively. The structure of the dimer was elucidated by X-ray crystallography and a plausible mechanism for its formation is depicted. Compound 3a couples with arene diazonium salts 4a-d to afford the hydrazo derivatives 5a-d; and reacts with hydrazine hydrate and phenylhydrazine 6a,b to afford the pyrazolo[3,4-h][1,6]naphthyridine derivatives7a,b; and with urea and thiourea 8a,b to afford the pyrimido[4,5-h][1,6]naphthyridine derivatives 9a,b, respectively.

Regiochemistry in alkylation, acylation and methoxycarbonylation of alkali salts from 2-substituted alkenylpropanedinitriles

Alkali salts (4-) of several 2-substituted alkenylpropanedinitriles are prepared, isolated and characterised by 1H and 13C NMR spectroscopy. By treating the salt 4a- with 4a a dimer, 2-dicyanomethylene-6-methyl-4,6-diphenyl-1,2,5,6-tetrahydronicotinonitrile 6, is formed, for which a single-crystal X-ray structure is presented. Alkylation of the ambident salts 4- with MeX (X = I, Tf, or Br) leads to regioisomers, 1-and 3-alkylation, and comparison with O vs. C-alkylation of ketones is made. Double alkylation is also observed, 3-alkylation followed by 1-alkylation. Thus from 4a- a mixture of (E)-and (Z)-2-methyl-2-(1-phenylprop-1-enyl)propanedinitrile 9b is formed, and the X-ray structure of the former is presented. Acylation of 4a- with benzoyl chloride gives only the 3-regioisomer; using equimolar amounts of reactants gives a ring-closure product, 2-oxo-4,6-diphenyl-2H-pyran-3-carbonitrile 12, while excess of benzoyl chloride gives the double-acylation product, (Z)-4,4-dicyano-1,3-diphenylbuta-1,3-dienyl benzoate (Z)-13, for which the X-ray structure is presented. Acylation of 4a- with acetyl chloride gives both regioisomers; the 1-acylated product evaded isolation, and the 3-acylation product reacted further to give the (E)- and (Z)-form of 4,4-dicyano-1-methyl-3-phenylbuta-1,3-dienyl acetate 15. The X-ray structure of the latter isomer, (Z)-15, is presented. Methoxycarbonylation of salts 4- with methyl chloroformate gives both regioisomers, while use of methyl cyanoformate gives only the 3-regioisomer, in addition to a Michael adduct from reaction of the CN- group with protonated salt 4-.

Synthesis of Cyanosubstituted Di- and Tetrahydropyridines in DIMCARB (Dimethylamine-CO2-Adduct)

A new selective method for base-catalyzed ring closure reaction of acetophenones (1a-1) with malononitrile in DIMCARB (dimethylamine-CO2-addition-compound) as solvent of high dimethy lamine concentration is reported, which allows effective syntheses of (1.2-dihydro-4-pyrid-6-yl)dicyanomethanides and 5-cyano-6-dicyanomethylene-1,2,3,6-tetrahydropyridines in good yields. The structure of the two new classes of compounds is proved by X-ray diffraction analysis.