41609-04-5Relevant articles and documents
Regioselective one-pot synthesis of functionalised 6,7-dihydro-1H-indol-4(5H )-ones
Alizadeh, Abdolali,Bayat, Fahimeh
, p. 166 - 169 (2015)
A one-pot two-step synthesis of functionalised 6,7-dihydro-1H-indol-4(5H )-ones from 1,3-cyclohexanediones, benzylamines, and 2-(2-oxo-2-phenylethylidene)-1H-indene-1,3(2H )-dione has been achieved. The advantages of this approach are operational simplicity, good yields of the products and avoidance of the use of any ligands, metal catalysts, acidic media, or column chromatography.
Cyclic enaminone as new chemotype for selective cyclooxygenase-2 inhibitory, anti-inflammatory, and analgesic activities
Kumar, Raj,Saha, Nirjhar,Purohit, Priyank,Garg, Sanjeev K.,Seth, Kapileswar,Meena, Vachan S.,Dubey, Sachin,Dave, Khyati,Goyal, Rohit,Sharma, Shyam S.,Banerjee, Uttam C.,Chakraborti, Asit K.
supporting information, (2019/08/26)
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.
Redox Property of Enamines
Li, Yao,Wang, Dehong,Zhang, Long,Luo, Sanzhong
, p. 12071 - 12090 (2019/10/11)
Enamines are electron-rich compounds bearing intriguing redox properties. Herein, a series of secondary enamines condensed from primary amine and β-ketocarbonyls were synthesized and their electrochemical oxidation properties were systematically studied by cyclic voltammetry. Furthermore, theoretical calculation of oxidation potentials of enamines, particularly those catalytic intermediates, was also conducted to further broaden the scope investigated. Possible structural factors on oxidation and the nature of the resulted radical cation intermediates were revealed and discussed. Correlation of redox potentials with molecular properties such as highest occupied molecular orbital energies and natural population analysis charge were explored, and there appears no simple linear correlation. On the other hand, a good correlation with Mayr's nucleophilicity parameter N was noted among a range of catalytically relevant enamines. Spin population analysis disclosed that enamine radical cations mainly exhibit the carbon-center free radical feature. Taking experimental and computation data together, a comprehensive picture about the redox property of enamines is presented, which would provide guidance in the development of oxidative enamine catalysis and transformations.
Cu catalyzed cross-dehydrogenative coupling reaction for the synthesis of 3-hydroxy-2-pyrrolidinones
Sarkar, Rajib,Mukhopadhyay, Chhanda
supporting information, p. 3069 - 3076 (2018/07/06)
A new convenient strategy for the synthesis of 3-hydroxy-2-pyrrolidinone derivatives featuring regioselective C–C coupling has been developed. This is a Cu (II) catalyzed cross dehydrogenative coupling (CDC) involving enamino-ketones of benzyl amines and di-alkyl acetylenedicarboxylate, followed by cyclization by primary amines. TBHP (tert-butyl hydroperoxide) has been used as the oxidant to promote the coupling protocol. This synthetic route principally demonstrates the scope of CDC reaction and also applicable to gram-scale synthesis.
An efficient method for retro-Claisen-type C-C bond cleavage of diketones with tropylium catalyst
Hussein,Huynh,Hommelsheim,Koenigs,Nguyen
supporting information, p. 12970 - 12973 (2018/11/23)
The retro-Claisen reaction is frequently used in organic synthesis to access ester derivatives from 1,3-dicarbonyl precursors. The C-C bond cleavage in this reaction is usually promoted by a number of transition-metal Lewis acid catalysts or organic Br?nsted acids/bases. Herein we report a new convenient and efficient method utilizing the tropylium ion as a mild and environmentally friendly organocatalyst to mediate retro-Claisen-type reactions. Using this method, a range of synthetically valuable substances can be accessed via solvolysis of 1,3-dicarbonyl compounds.
Hypervalent Iodine-Promoted Aromatization of Exocyclic β-Enaminones for the Synthesis of meta-N,N-Diarylaminophenols
Bhattacherjee, Dhananjay,Thakur, Vandna,Shil, Arun K.,Das, Pralay
supporting information, p. 2202 - 2208 (2017/07/07)
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.).
Continuous flow iodination using an automated computer-vision controlled liquid-liquid extraction system
O'Brien, Matthew,Cooper, Dennis A.,Dolan, Jonathan
, p. 829 - 834 (2017/02/10)
A dynamic computer-vision control system incorporating open-source software technologies (Python, OpenCV) was used to automate a gravity based in-line liquid-liquid extraction during the iodination of enaminones in continuous flow. The system was able to cope with significant colouration of the organic reaction stream and with significant volume/flow changes in the aqueous and organic phase streams due to extraction of the water soluble acetonitrile co-solvent.
Library design, synthesis and biological exploration of novel 3,4′-bicarbostyril derivatives as potent antimicrobial, antitubercular and antimalarial agents
Jardosh, Hardik H.,Vala, Nileshkumar D.,Patel, Manish P.
, p. 881 - 899 (2017/04/13)
Abstract: A library comprises diversely substituted novel 3,4′-bicarbostyril derivatives have been designed by molecular hybridization technique and synthesized via multi-component reaction. Compounds G22 (MIC = 12.5 μg/mL) and G38 (MIC = 25 μg/mL) exhibited 99% inhibition against Mycobacterium tuberculosis, while compounds G40 (IC50 = 0.019 μg/mL) and G20 (IC50 = 0.028 μg/mL) found to have excellent activity against Plasmodium falciparum. Compounds G37 (MIC = 25 μg/mL) and G8, G18, and G38 (MIC = 50 μg/mL) elicited excellent antimicrobial activity compared to standard drugs. Biological results revealed that the potency of the title compounds strongly depends on the length and flexibility of various spacers at N?1, the electronic influence of substituent at R1 and lipophilicity of CH3 group at R2 position on bicarbostyril system. Graphical Abstract: [InlineMediaObject not available: see fulltext.]
Nano-SiO2 catalyzed synthesis of β-enaminones under solvent free conditions
Alinezhad, Heshmatollah,Tajbakhsh, Mahmood,Sarkati, Malihe Norouzi,Zare, Mahboobe
, p. 1591 - 1596 (2016/08/16)
Nano-SiO2 efficiently catalyzed the synthesis of β-enaminones using direct condensation of various (cyclic and acyclic) β-diketones with aromatic and aliphatic amines under solvent-free conditions. This eco-friendly catalyst can be recovered and reused without significant loss of activity. This methodology provides a simple synthetic route to enaminones in excellent yields at room temperature. Graphical abstract: [Figure not available: see fulltext.]
Continuous Flow Liquid-Liquid Separation Using a Computer-Vision Control System: The Bromination of Enaminones with N -Bromosuccinimide
O'Brien, Matthew,Cooper, Dennis
supporting information, p. 164 - 168 (2015/12/26)
Incorporating open-source software components (Python, OpenCV), a computer-vision system was used to control the interface level in a gravity-based inline liquid-liquid separation device. This was used in the continuous flow bromination of a series of enaminone substrates. The main byproduct of the reaction, succinimide, was efficiently extracted into the aqueous stream, providing clean products without the need for further purification.
