Synthesis and stability of strongly acidic benzamide derivatives

Abstract

Reactivity studies of strong organic acids based on the replacement of one or both of the oxygens in benzoic acids with the trifluoromethanesulfonamide group are reported. Novel derivatives of these types of acids were synthesized in good yields. The generated N-triflylbenzamides were further functionalized through cross-coupling and nucleophilic aromatic substitution reactions. All compounds were stable in dilute aqueous solutions. Studies of stability under acidic and basic conditions are also reported.

Lignin‐Inspired Polybenzylethersulfone Synthesis via SNAr Reaction

“…Based on our broad experience with S N Ar‐based chemistry, we envisioned that this methodology could be expanded to the synthesis of HTP polyethers from lignin‐derivable monomers. [ 21–23 ] We rationalized that the incorporation of aliphatic ether bonds similar to the ones found in lignin could enhance the potential degradability of the polymer. Two diols, 4‐hydroxybenzyl alcohol (4‐HBA, gastrodigenin) and 2‐(4‐hydroxyphenyl)ethanol (4‐HPEA, tyrosol), were chosen as simple model structures of the natural lignin precursors, namely para‐ coumaryl, coniferyl, and sinapyl alcohol.…”

Synthesis, Characterization and Insilico Toxicity Prediction, Anti-Microbial Study of Ortho-Amino Substituted Benzamide Derivatives

“…Benzamides are an identical structural unit present in many compounds having biological activities. They are synthesized from different organic sources that are extracted from natural sources 1,2 . For example proteins play an essential role in all biological process such as immune protection, enzyme catalysis, transport or storage (hemoglobin's) and mechanical support (collagen).…”

Dihydroquinazolinones via A3‐Type Reactions of N‐Carbamoyliminium Ions

“…In the first step, hydrogenationo ft he nitro group under basic conditions led to the correspondinga niline,w hich wasc onverted into the pentafluoroophenyl carbamate by reaction with bis-pentafluoroophenylc arbonate. Based on prior experience with nucleophilic aromatic substitution (S N Ar) reactions [37][38][39][40] we presumed that the fluoro-substituent could be exchanged via an S N Ar reaction. After testing various conditions, the formation of the corresponding methoxy-substituted derivative ( 22)i na92 %y ield was obtained from adding solid sodium hydroxide to am ethanol solution of 20.T he intermediate (22)w as subsequently converted to pentafluorophenyl carbamate 23 in 94 %y ield, followingt he same procedure as for the synthesis of 21.…”