scholarly journals An Unprecedented Straightforward Synthesis of Chiral Pyrrolo[3,4-b]quinolone and Pyrrolo[3,2-b]quinolone Backbones Starting fromtrans-4-Hydroxy-L-proline

2016 ◽  
Vol 2016 ◽  
pp. 1-5
Author(s):  
Sébastien Comesse ◽  
Adam Daïch
Keyword(s):  
Carbonyl Compounds ◽  
Good Yield ◽  
Anticancer Activities ◽  
Carbonyl Derivatives

The straightforward synthesis of pyrrolo[3,4-b]quinolone and pyrrolo[3,2-b]quinolone backbones, which can be found in molecules exhibiting anticancer activities, is presented. The key step of the process is an efficient and unprecedented Friedländer condensation between an oxoproline carbamate, obtained in 3 steps and good yield starting from commercially available and relatively cheaptrans-4-hydroxy-L-proline, and various 2-amino-substituted carbonyl derivatives. It was demonstrated that the formation of the two possible regioisomers was fully triggered by both the R substituent onto the 2-amino-substituted carbonyl compounds and the ester function onto the oxoproline carbamate. Thus, in some cases, a complete regiocontrol for the Friedländer reaction could be attained.

scholarly journals Transition Metal-Catalyzed α-Position Carbon–Carbon Bond Formations of Carbonyl Derivatives

Catalysts ◽  
2020 ◽  
Vol 10 (8) ◽  
pp. 861 ◽  
Author(s):  
Ha-Eun Lee ◽  
Dopil Kim ◽  
Ahrom You ◽  
Myung Hwan Park ◽  
Min Kim ◽  
...  
Keyword(s):  
Transition Metal ◽  
Carbonyl Compounds ◽  
Bond Formation ◽  
Chiral Ligand ◽  
Catalytic Systems ◽  
Carbon Bond ◽  
Carbonyl Derivatives ◽  
Carbon Carbon Bond ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

α-Functionalization of carbonyl compounds in organic synthesis has traditionally been accomplished via classical enolate chemistry. As α-functionalized carbonyl moieties are ubiquitous in biologically and pharmaceutically valuable molecules, catalytic α-alkylations have been extensively studied, yielding a plethora of practical and efficient methodologies. Moreover, stereoselective carbon–carbon bond formation at the α-position of achiral carbonyl compounds has been achieved by using various transition metal–chiral ligand complexes. This review describes recent advances—in the last 20 years and especially focusing on the last 10 years—in transition metal-catalyzed α-alkylations of carbonyl compounds, such as aldehydes, ketones, imines, esters, and amides and in efficient carbon–carbon bond formations. Active catalytic species and ligand design are discussed, and mechanistic insights are presented. In addition, recently developed photo-redox catalytic systems for α-alkylations are described as a versatile synthetic tool for the synthesis of chiral carbonyl-bearing molecules.

scholarly journals Correction: Surowiak, A.K.; Lochyński, S.; Strub, D.J. Unsubstituted Oximes as Potential Therapeutic Agents. Symmetry 2020, 12, 575

Symmetry ◽  
2020 ◽  
Vol 12 (6) ◽  
pp. 1006
Author(s):  
Alicja K. Surowiak ◽  
Stanisław Lochyński ◽  
Daniel J. Strub
Keyword(s):  
Biological Activity ◽  
Adjuvant Therapy ◽  
Chemical Synthesis ◽  
Carbonyl Compounds ◽  
Therapeutic Agents ◽  
Bioactive Molecules ◽  
Anticancer Activities ◽  
Medical Sector ◽  
Cancer And Inflammation ◽  
Increased Activity

Oximes, which are highly bioactive molecules, have versatile uses in the medical sector and have been indicated to possess biological activity. Certain oximes exist in nature in plants and animals, but they are also obtained by chemical synthesis. Oximes are known for their anti-inflammatory, antimicrobial, antioxidant and anticancer activities. Moreover, they are therapeutic agents against organophosphate (OP) poisoning. Two oximes are already commonly used in therapy. Due to these abilities, new oxime compounds have been synthesized, and their biological activity has been verified. Often, modification of carbonyl compounds into oximes leads to increased activity. Nevertheless, in some cases, oxime activity is connected to the activity of the substrate. Recent works have revealed that new oxime compounds can demonstrate such functions and thus are considered to be potential drugs for pathogenic diseases, as adjuvant therapy in various types of cancer and inflammation and as potential next-generation drugs against OP poisoning.

A new tandem synthesis of bis(β,β′-dialkoxy carbonyl) compounds by oxidative cleavage of aziridines under metal-free conditions

2020 ◽  
Vol 18 (3) ◽  
pp. 551-556 ◽  
Author(s):  
Satyajit Samanta ◽  
Sougata Santra ◽  
Rana Chatterjee ◽  
Adinath Majee
Keyword(s):  
Carbonyl Compounds ◽  
Oxidative Cleavage ◽  
One Pot ◽  
Metal Free ◽  
One Pot Synthesis ◽  
Carbonyl Derivatives ◽  
Tandem Synthesis

One-pot synthesis of bis(β,β′-dialkoxy carbonyl) derivatives has been reported by the oxidative cleavage of aziridines.

1-Butylimidazole-derived ionic liquids: synthesis, characterisation and evaluation of their antibacterial, antifungal and anticancer activities

RSC Advances ◽  
2014 ◽  
Vol 4 (96) ◽  
pp. 53634-53644 ◽  
Author(s):  
Prabodh Ranjan ◽  
Bheru Singh Kitawat ◽  
Man Singh
Keyword(s):  
Ionic Liquids ◽  
Good Yield ◽  
Solvent Free ◽  
Anticancer Activities ◽  
Antifungal Activities ◽  
Antibacterial And Antifungal Activities ◽  
Antibacterial And Antifungal

The reaction of 1-butylimidazole (1a) with aryl/alkoxy halides (2a–h) using a microwave solvent-free approach delivered imidazolium-based ILs (3a–h) in good yield. Some of them showed promising antibacterial and antifungal activities.

Nitrones and oxaziridines. XIII. A convenient method for the oxidation of primary- and secondary-alkyl amines to carbonyl compounds

1975 ◽  
Vol 28 (11) ◽  
pp. 2547 ◽  
Author(s):  
DSC Black ◽  
NA Blackman
Keyword(s):  
Convenient Method ◽  
Carbonyl Compounds ◽  
Good Yield ◽  
Acidic Hydrolysis ◽  
Alkyl Amines ◽  
Hydrolysis Of

Primary- and secondary-alkyl amines have been converted in good yield into the related carbonyl compounds by sequential conversion into isopropylidene imines and 3,3-dimethyloxaziridines, followed by acidic hydrolysis of the latter. Intermediates need not be isolated.

Organometallic reactions in aqueous media — Antimony-mediated allylation of carbonyl compounds and the nature of allylstibine intermediates

2001 ◽  
Vol 79 (11) ◽  
pp. 1536-1540
Author(s):  
Lian-Hai Li ◽  
Tak Hang Chan
Keyword(s):  
Carbonyl Compounds ◽  
Good Yield ◽  
Allyl Bromide ◽  
Aqueous Media ◽  
Organometallic Reactions ◽  
Homoallylic Alcohols ◽  
Reaction Proceeds

Commercial antimony metal, in aqueous 1 M H(D)Cl solution, reacts with allyl bromide and aldehydes to give the corresponding homoallylic alcohols in good yield. The reaction proceeds through the formation of allylstibine intermediates. The structures of the allylstibine intermediates are likely to be allylstibine dibromide and diallylstibine bromide.Key words: allylation reaction, aqueous organometallic reactions, homoallylic alcohols, allylstibine dibromide, diallylstibine bromide.

Electrophilic fluorination of stereodefined disubstituted silyl ketene hemiaminals en route to tertiary α-fluorinated carbonyl derivatives

2018 ◽  
Vol 16 (7) ◽  
pp. 1079-1082 ◽  
Author(s):  
Jian Qiang Huang ◽  
Zackaria Nairoukh ◽  
Ilan Marek
Keyword(s):  
Carbonyl Compounds ◽  
Diastereoselective Synthesis ◽  
Carbonyl Derivatives ◽  
Electrophilic Fluorination

A highly diastereoselective synthesis of tertiary α-fluoro carbonyl compounds is reported in only two chemical steps from a simple alkyne through the reaction of stereodefined fully substituted silyl ketene hemiaminal derivatives with Selectfluor.

scholarly journals Bioactive Phytochemicals: Efficient Synthesis of Optically Active Substituted Flav-3-enes and Flav-3-en-3-o-R Derivatives

2017 ◽  
Vol 2017 ◽  
pp. 1-11
Author(s):  
Matthew Chilaka Achilonu ◽  
Moosa Mahmood Sedibe ◽  
Karabo Shale
Keyword(s):  
Good Yield ◽  
Biological Activities ◽  
Optically Active ◽  
Synthetic Chemistry ◽  
Efficient Synthesis ◽  
Anticancer Activities ◽  
Wide Range ◽  
Significant Interest ◽  
Bioactive Phytochemicals ◽  
Pharmacological Profiles

The structural core of flavene (2-phenyl-2H-chromene) is commonly found in plant flavonoids, which exhibit a wide range of biological activities and diverse pharmacological profiles (e.g., antioxidant and anticancer activities). Flavonoids have attracted significant interest in medicinal and synthetic chemistry. Substituted flav-3-ene 13 was exclusively synthesized by the stereoselective elimination of the O-mesyl moiety on C-3 of 5,7,3′,4′-tetramethoxyflavan-3-mesylate 12 with 1,8-diazabicyclo[5.4.0]undec-7-ene. The reaction of 5,7,3′,4′-tetramethoxyflavan-3-one 15 with ytterbium trifluoromethanesulfonate in methanol afforded a novel 3-O-substituted flav-3-ene derivative (3,5,7,3′,4′-pentamethoxyflav-3-ene) 17. The reduction of 4-(1,3,5-trihydroxybenzene)-5,7,3′,4′-tetra-O-benzylflavan-3-one 19b with hydrogen afforded a new compound: 3-hydroxy-4-(1,3,5-trihydroxybenzene)-5,7,3′,4′-tetrahydroxyflavan-3-en-3-ol 21 in good yield (95%), while the acetylation of 19a and 21 afforded the expected novel flav-3-en-3-acetoxy derivatives 20 (92%) and 22 (90%), respectively.

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