scholarly journals Highly selective electrochemical fluorination of dithioacetal derivatives bearing electron-withdrawing substituents at the position α to the sulfur atom using poly(HF) salts

2015 ◽  
Vol 11 ◽  
pp. 85-91 ◽  
Author(s):  
Bin Yin ◽  
Shinsuke Inagi ◽  
Toshio Fuchigami
Keyword(s):  
Sulfur Atom ◽  
Nitrile Group ◽  
Amide Group ◽  
Sharp Contrast ◽  
Product Selectivity ◽  
Electrochemical Fluorination ◽  
Weak Electron ◽  
Electron Withdrawing Substituents

Anodic fluorination of dithioacetals bearing electron-withdrawing ester, acetyl, amide, and nitrile groups at their α-positions was comparatively studied using various supporting poly(HF) salts like Et3N·nHF (n = 3–5) and Et4NF·nHF (n = 3–5). In the former two cases, the corresponding α-fluorination products or fluorodesulfurization products were obtained selectively depending on supporting poly(HF) salts used. In sharp contrast, in the latter two cases, fluorination product selectivity was strongly affected by the electron-withdrawing ability of α-substituents: A dithioacetal bearing a relatively weak electron-withdrawing amide group provided a fluorodesulfurization product selectively while a dithioacetal having a strongly electron-withdrawing nitrile group gave the α-fluorination product predominantly regardless of the poly(HF) salts used.

Aromatic amides. VIII. Z,E Isomer ratios and stereochemistry about aryl-nitrogen bonds in N-aryl amides and thioamides

1974 ◽  
Vol 27 (12) ◽  
pp. 2611 ◽  
Author(s):  
DL Bate ◽  
ID Rae
Keyword(s):  
Amide Group ◽  
Isomer Ratio ◽  
Ring Plane ◽  
Nitrogen Bonds ◽  
Electron Withdrawing Substituents

For 4?-substituted 2?,6?-diethylacetanilides, the Z/E isomer ratio depends on the nature of the 4?- substituent, the Z isomer being relatively favoured by electron-withdrawing substituents. The acyla- tion shifts of the ortho aromatic protons for 4?-substituted thiopivalanilides are greatest when the substituent is electron- withdrawing. These relationships complement the previously observed changes in isomer ratios of thioamides and acylation shifts of amides. It is proposed that the Z isomer is more nearly planar when the 4?- substituent is electron-withdrawing. As the substituent becomes more electron-releasing, the amide group is able to twist more out of the ring plane and the Z isomer is destabilized, relative to the E isomer, by n-π electron repulsions.

Coulomb disintegration of weak electron fluxes and the photocounts

1995 ◽  
Vol 165 (8) ◽  
pp. 955 ◽  
Author(s):  
Vladimir P. Bykov ◽  
A.V. Gerasimov ◽  
V.O. Turin
Keyword(s):  
Weak Electron

Photocatalytic Alkylation of Pyrroles and Indoles with α-Diazo Esters

2019 ◽  
Author(s):  
Łukasz Ciszewski ◽  
Jakub Durka ◽  
Dorota Gryko
Keyword(s):  
Aromatic Compounds ◽  
Reaction Pathway ◽  
Alkylating Agents ◽  
Catalytic Amount ◽  
Radical Formation ◽  
Reaction Selectivity ◽  
Diazo Esters ◽  
Electron Withdrawing Substituents

This article describes direct photoalkylation of electron-rich aromatic compounds with diazo compoiunds. C-2 alkylated indoles and pyrroles are obtained with good yields even though the photocatalyst (Ru(bpy)3Cl2) loading is as low as 0.075 mol %. For substrates bearing electron-withdrawing substituents the addition of a catalytic amount of N,N-dimethyl-4-methoxyaniline is required. Both EWG-EWG and EWG-EDG substituted diazo esters are suitable as alkylating agents. The reaction selectivity and mechanistic experiments suggest that carbenes/carbenoid intermediates are not involved in the reaction pathway, instead radical formation is proposed.

The Gender Troubles of Feofan Prokopovich

2020 ◽  
Vol 54 (1-3) ◽  
pp. 198-228
Author(s):  
Gary Marker
Keyword(s):  
Sharp Contrast ◽  
Close Reading ◽  
Dual Codes ◽  
Minimalist Approach ◽  
Holy Women ◽  
Gender Trouble

Abstract This essay constitutes a close reading of the works of Feofan Prokopovich that touch upon gender and womanhood. Interpretively it is informed by Judith Butler’s book Gender Trouble, specifically by her model of gender-as-performance. Prokopovich’s writings conveyed a negative characterization of holy women and Russian women of power, a combination of glaring silences and Scholastic dual codes that in toto denied the association of womanhood with glory or wisdom. In this he stood apart from other East Slavic Orthodox homilists of his day, even though they too invariably associated virtue with masculinity (muzhestvo). For Prokopovich, wisdom, strength, constancy, etc., were innately masculine. Women, by contrast, were weak, inconstant, non-rational, and guided by emotion. His sermons nominally in praise of Catherine I and Anna Ioannovna were suffused with narrative gestures that, to those attuned to the nuances of Scholastic rhetoric, ran entirely counter to their nominal message. Several panegyrics to Anna, for example, made no mention of her at all, a practice in sharp contrast to his sermons to male rulers, which typically placed the honoree firmly in the foreground. Even more startling is his singularly minimalist approach to Mary, for whom he composed almost no sermons and whose presence he barely mentioned in tracts where one would have expected otherwise. This essay concludes that this attitude reflected both his personal preferences and influence that Protestant Pietism had on his thinking.

Synthesis and Biological Properties of some New Lead Sulphonamide and Carboxamide Scaffolds Bearing Coumarin Moiety (Mini Review)

2020 ◽  
Vol 20 ◽  
Author(s):  
Cosmas Chinweike Eze ◽  
Mercy Amarachukwu Ezeokonkwo ◽  
Benjamin Ebere Ezema ◽  
Abraham Efeturi Onoabedje ◽  
David Izuchukwu Ugwu
Keyword(s):  
Biological Properties ◽  
Therapeutic Agents ◽  
Amide Group ◽  
Pharmacological Properties ◽  
Important Class ◽  
Synthetic Route ◽  
Therapeutic Activities

: Coumarin, sulphonamide and amide scaffolds exhibit diverse pharmacological features and constitute an important class of therapeutic agents. In this review, we have discussed the synthesis, biological properties, and SAR of coumarins containing sulphonamide or amide group in the last seven years. Many reviews on the therapeutic activities of coumarins, sulphonamides, and amides have been published, hence the authors focused on coumarin-linked sulphonamide or amide scaffolds. The review provides information on the synthetic route to new coumarins containing sulphonamide or amide groups with improved pharmacological properties.

(Substituted)-benzo[b]thiophene-4-carboxamide Synthesis and Antiproliferative Activity Study

2020 ◽  
Vol 17 (5) ◽  
pp. 563-573 ◽  
Author(s):  
Chandrakant Dhondiram Pawar ◽  
Dattatraya Navnath Pansare ◽  
Devanand Baburao Shinde
Keyword(s):  
Anticancer Activity ◽  
Cell Lines ◽  
Proliferative Activity ◽  
Thiophene Ring ◽  
Amide Group ◽  
Peptide Coupling ◽  
Ic50 Value ◽  
Important Building Block ◽  
Mcf 7

Background: Thiophene ring forms important building block in medicinal chemistry. Literature reveals that thiophene ring in combination with different groups shows different activity. By keeping these things in mind we have designed and synthesized a new series of amide and sulfonamide coupled thiophene. A series of novel substituted 3-sulfamoylbenzo[b]thiophene-4- carboxamide molecules containing sulfonamide and amide group were designed, synthesized and used for anti-proliferative activity study. Methods: The final compounds 16-36 were synthesized by using series of reactions comprising sulfonation, sulfonamide coupling, hydrolysis and peptide coupling. The yields of compounds 16- 36 are in the range of 90-98%. The structures of the synthesized compounds were elucidated and confirmed by 1H NMR, 13C NMR, LCMS and the purity was checked through HPLC analysis. The compounds were further tested for their in vitro anticancer activity against a series of cell lines A549, HeLa, MCF-7 and Du-145. Results: The intermediates 8-13, 15 and final compounds 16-36 were synthesized in good yields. The synthesized compounds were further tested for their anticancer activity and most of compounds showed moderate to good anticancer activity against all four cell lines. Conclusion: We have synthesized 21 compounds and were screened for anticancer activity against MCF-7, HeLa, A-549 and Du-145 cancer cell lines. Most of the compounds were active for tested cell lines with IC50 value in the range of 1.81 to 9.73 μM. The compounds 18, 19, 21, 25, 30, 31 and 33 are most active in cell line data with IC50 value in the range of 1.81 to 2.52 μM.

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