51408-72-1

Upstream product

• 504-02-9 1,3-cylohexanedione 
• 108-44-1 1-amino-3-methylbenzene 
• 765-87-7 cyclohexane-1,2-dione 

Downstream Products

• 85049-96-3 3-m-Toluidino-phenol 

Relevant academic research and scientific papers

Iodine(III)-Promoted Ring Contractive Cyanation of Exocyclic β-Enaminones for the Synthesis of Cyanocyclopentanones

A highly efficient hypervalent iodine-promoted regiocontrolled ring contractive cyanation (RCC) reaction of exocyclic β-enaminones for the synthesis of cyanocyclopentanone (CCP) was demonstrated at ambient temperature with a wide substrate scope. The meth

Hypervalent Iodine-Promoted Aromatization of Exocyclic β-Enaminones for the Synthesis of meta-N,N-Diarylaminophenols

A metal- and additive-free milder cascade approach for the synthesis of meta-N,N-diarylaminophenols (DAAP) starting from exocyclic β-enaminones has been developed. The feasibility of the process is rationalized by the suitable molecular geometry of β-enaminones for tandem N-arylative α-iodination and aromatization under milder basic conditions. Furthermore, the developed strategy has been extended to the synthesis of meta-N-benzyl-N-arylaminophenols (BAAP). 4-Ethylpropionyl-2-cyclohexenone has been explored to give 7-diarylaminochroman-2-one (DAAC) by employing a similar one-pot approach. The plausible mechanistic steps were deduced based upon isolation of a stable intermediate and structural identification through X-ray crystallographic analysis. (Figure presented.).

Synthesis, crystal structure and effect of indeno[1,2-b]indole derivatives on prostate cancer in vitro. Potential effect against MMP-9

A highly regiospecific synthesis of a series of indenoindoles is reported, together with X-ray studies and their activity against human prostate cancer cells PC-3 and LNCaP in vitro. The most effective compound 7,7-dimethyl-5-[(3,4-dichlorophenyl)]-(4bRS,9bRS)-dihydroxy-4b,5,6,7,8,9bhexahydro-indeno[1,2-b]indole-9,10-dione 7q reduced the viability in both cell lines in a time and dose-dependent manner. Inhibitory effects were also observed on the adhesion, migration, and invasion of the prostate cancer cells as well as on clonogenic possibly by inhibition of MMP-9 activity. Molecular docking of 7q and 6k into MMP-9 human active site was also performed to determine the probable binding mode.

Palladium-catalyzed synthesis of natural and unnatural 2-, 5-, and 7-oxygenated carbazole alkaloids from N-arylcyclohexane enaminones

A palladium-catalyzed synthesis of the carbazole framework is described, including the preparation of 2-, 5-, and 7-oxygenated natural and unnatural carbazole alkaloids. A series of N-arylcyclohexane enaminones, generated by condensation of cyclohexane-1,3-dione with diverse anilines, were aromatized by a Pd(0)-catalyzed thermal treatment to afford the corresponding diarylamines. The latter were submitted to a Pd(II)-catalyzed cyclization and methylation processes to provide the desired carbazoles, including clausine V. Following an inverse strategy, a new and short total synthesis of glycoborine is also reported.

NMR of enaminones part 3 ? - 1H, 13C and 17O NMR spectroscopic studies of acyclic and cyclic N-aryl enaminones: Substituent effects and intramolecular hydrogen bonding

17O, 13C and 1H NMR spectra for para-and meta-substituted 4-arylaminopent-3-en-2-ones (acyclic enaminones, 1 and 2) and 3-arylaminocyclohex-2-en-1-ones (cyclic enaminones, 3 and 4) are reported. The 17O, 13C and 1H shift values of these enaminones correlate well with σm0 and σp- constants in the correlations for meta and para derivatives, and with pKa values of the corresponding anilines. Dual substituent parameters analyses were also performed. Correlations of 17O and 13C chemical shifts of the carbonyl groups with those of the corresponding N-acylanilines indicate that the enaminone moiety as a whole has electronic properties similar to those of the RCONH group. The 17O shift values of the carbonyl O atoms of enaminones correlate well with their 1H and 13C data. Shieldings of 33-45 ppm for O atoms are observed for 1 and 2 compared with 3 and 4, respectively. This is attributed to intramolecular hydrogen bonding.