36646-76-1

Upstream product

• 765-87-7 cyclohexane-1,2-dione 
• 100-01-6 4-nitro-aniline 
• 504-02-9 1,3-cylohexanedione 

Downstream Products

• 1206477-73-7 C₂₇H₂₃ClN₆O₃ 
• 1206477-67-9 2-amino-4-(5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)-1-(4-nitrophenyl)-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carbonitrile 
• 1260425-49-7 3-[(methyl)(4-nitrophenyl)amino]cyclohex-2-enone 
• 1396649-85-6 3-(bis(4-nitrophenyl)amino)phenol 
• 1394901-89-3 2-(4-nitrophenyl)pyrrolo[2,3,4-kl]acridin-1(2H)-one 
• 1431986-11-6 3-(4-hydroxy-2-oxo-2H-chromen-3-yl)-6,6-dimethyl-1,2-diphenyl-6,7-dihydro-1H-indol-4(5H)-one 
• 1396649-65-2 6-nitro-9-(4-nitrophenyl)-2,3-dihydro-1H-carbazol-4(9H)-one 
• 1396650-03-5 3-(bis(4-nitrophenyl)amino)-2-iodocyclohex-2-enone 
• 1220515-90-1 2-iodo-3-[(3-nitrophenyl)(4-nitrophenyl)amino]cyclohex-2-enone 
• 1220515-77-4 2-iodo-3-[(4-nitrophenyl)(phenyl)amino]cyclohex-2-enone 

Relevant academic research and scientific papers

Synthesis, polymorphic characterization and structural comparisons of the non-linear optically active and inactive forms of polymorphs of 3-(nitroanilino)cycloalk-2-en-1-ones

Three 3-(nitroanilino)cycloalk-2-en-1-ones have been synthesized and their non-linear optical (NLO) properties investigated. Two of these compounds have been found to exist in two polymorphic forms (α and β) that exhibit different second-order NLO properties. These polymorphic forms were prepared and characterized by second-harmonic generation measurements as well as the more conventional methods of X-ray powder diffraction and infrared spectroscopy. Of these polymorphs, the α- and β-forms of 3-(4-nitroanilino)cyclohex-2-en-1-one (4NACHD) have been further characterized by X-ray single-crystal diffraction and the crystal structures obtained have been compared with each other to rationalize why these two crystalline forms exhibit different second-order NLO properties. The α-form of 4NACHD crystallizes in a centrosymmetric space group (P21/c) with a = 6.863(7), b = 12.767(3), c = 13.410(4) A, β = 104.59 (5)°, Z = 4, Dc = 1.356 g cm-3 and R = 0.046, whereas the β-form crystallizes in a non-centrosymmetric space group (P212121) with a = 7.228(3), b = 12.064(3), c = 13.104(3) A, Z = 4, Dc = 1.350 g cm-3 and R = 0.076. Except for the slight difference in bond distances, both the α- and β-forms have the same orientation of the carbonyl group and hydrogen-bonding interactions. The carbonyl group is anti to the N-H group in both the two forms that result in the lambda (Λ) conformation. The whole molecule of 4NACHD is more twisted in the β-form than in the α-form. Based on structural comparisons of the polymorphs of 4NACHD and other compounds, the more twisted conformation in the β-form may bias molecules to pack into a non-centrosymmetric structure. Preliminary results suggest that 3-(nitroanilino)cycloalk-2-en-1-one compounds may have a higher chance of forming non-centrosymmetric crystal structures than normal achiral organic molecules.

Hypervalent Iodine(III)-Mediated Counteranion Controlled Intramolecular Annulation of Exocyclic β-Enaminone to Carbazolone and Imidazo[1,2-a]pyridine Synthesis

A highly efficient and flexible protocol for intramolecular annulation of exocyclic β-enaminones has been disclosed for the synthesis of carbazolones and imidazo[1,2-a]pyridines through a counter-anion-controlled free-radical mechanism promoted by hypervalent iodine(III). The cooperative behavior of HTIB and AgSbF6 plays a crucial role in the intramolecular annulation process through C?C and C?N bond formation to give the desired products. The mechanistic insights suggest that the two competitive reactions involved in the system are guided by the nature of the counteranion, which determines the formation of the final products. A wide variety of carbazolones and imidazo[1,2-a]pyridine molecules have been prepared and isolated in good to excellent yields.

Cyclic enaminone as new chemotype for selective cyclooxygenase-2 inhibitory, anti-inflammatory, and analgesic activities

The cyclic enaminone moiety has been identified as a new scaffold for selective inhibition of cyclooxygenase-2 with anti-inflammatory and analgesic activities. The designed cyclic enaminones have been synthesized conveniently through the development of a new catalyst-free methodology and evaluated for cyclooxygenase (COX-1 and COX-2) inhibitory activities. Three compounds 7d, 8, and 9 predominantly inhibited COX-2 with selectivity index of 74.09, 19.45 and 108.68, respectively, and were assessed for in vivo anti-inflammatory activity in carrageenan induced rat paw edema assay. The anti-inflammatory activity of 7d was comparable to that of celecoxib at a dose of 12.5 mg/kg. However, the compounds 8 and 9 were more/equally effective as anti-inflammatory agent compared to celecoxib at the doses of 12.5 mg/kg and 25 mg/kg and also exhibited anti-inflammatory activity comparable to that of diclofenac. The therapeutic potential of the most active compound 9 was further assessed by performing in vivo thermal and mechanical hyperalgesia tests using various models that revealed its analgesic activity. The in vivo non-ulcerogenicity of 9 revealed the gastrointestinal safety as compared to the non-selective COX inhibitor indomethacin. The in vitro antioxidant activity and in vivo experiments on heart rate and blood pressure provided the cardiovascular safety profile of 9. The molecular docking studies rationalize the COX-2 selectivity of the newly found anti-inflammatory compounds 7d, 8, and 9.

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.).

Tailoring of spectral response and intramolecular charge transfer in β-enaminones through band gap tuning: Synthesis, spectroscopy and quantum chemical studies

In this paper, we investigate the synthetic tailoring of the spectral response and intramolecular charge transfer (ICT) of β-enaminones through bandgap modulation. Two donor/acceptor substituted β-enaminones, namely, 3-(4-methoxyphenylamino)-2-cyclohexen-1-one (OACO) and 3-(4-nitrophenylamino)-2-cyclohexen-1-one (NACO) have been synthesized along with their unsubstituted counterpart, 3-(phenylamino)-2-cyclohexen-1-one (PACO). Steady state as well as time resolved spectroscopic techniques with picosecond resolution are used to record their spectral responses. Substitution of the donor group (-OCH3) mildly enhances the charge transfer from the phenyl ring to the enaminone moiety, while substitution of the acceptor group (-NO2) jeopardizes the charge transfer through mutual electron withdrawing effects of PNA and enaminone moieties. Combined experimental and quantum chemical investigations reveal that the ground state photophysics of OACO and NACO in water are controlled by both microscopic and macroscopic solvation with dominant contribution from the former. Time dependent density functional theory (TDDFT) calculations predict that the HOMO to [LUMO+1] transition gives rise to the absorption spectra of OACO in water, while the absorption by the enaminone moiety of NACO arises as a result of a HOMO to LUMO transition. A crossing between the first (S1) and the second excited (S2) states takes place in the microclusters of PACO, OACO and NACO with water. The intersystem crossing (ISC) has been found to be the major reason for low quantum yields in these molecules. The band gap modulation through waxing and waning of the conjugation strength is expected to throw light on many ICT-driven processes and provides means of tuning the properties depending on it.

Synthesis of N-substituted carbazolones from α-iodo enaminones via Pd(0)-catalyzed intramolecular coupling under microwave irradiation

A variety of N-aryl and N-alkyl carbazolones were conveniently achieved in good to high yields via Pd2(dba)3-mediated intramolecular coupling of N-substituted α-iodo enaminones under microwave irradiation. The Pd(0)-catalyzed cyclization was found to proceed favorably with the more electron-deficient phenyl ring during the reactions involving unsymmetrical N,N-diaryl α-iodo enaminones. This unique property enables the construction of carbazolone skeleton containing nitro substituted benzenoid ring.

Mild and efficient method for synthesis of eaminones using ytterbium triflate as catalyst

A mild and efficient procedure for synthesis of-enaminones by the condensation of-dicarbonyl compounds and amines using ytterbium triflate [Yb(OTf)3] as catalyst is described. The catalyst can be easily recovered and reused without loss of activity. Taylor & Francis Group, LLC.

Concurrent α-iodination and N-arylation of cyclic β-enaminones

A variety of N-substituted 3-aminocyclohex-2-enones were converted into the corresponding N-arylated α-iodo enaminones in high yields via concurrent N-iodination and N-arylation mediated by ArI(OAc)2. A mechanism is postulated to account for the reaction differences between the cyclic and the acyclic -enaminones, which undergo predominant β-acetoxylation under the same reaction conditions.

Solid-state synthesis of β-enamino ketones from solid 1,3-dicarbonyl compounds and ammonium salts or amines

A facile amination of solid 1,3-dicarbonyl compounds with ammonium salts or amines in solid state has been achieved by mechanochemical grinding in the presence of KHSO4 and SiO2. Most of the reactions proceed smoothly at room temperature under solid-state conditions and give their corresponding β-imino derivatives in high yields. The method has the advantage of simple manipulation and mild conditions. Georg Thieme Verlag Stuttgart.

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.