Synthesis and X-ray crystal structure of unexpected novel thiazolidinone/1,3,4-thiadiazole heterocycle via S-alkylation and Smiles rearrangement dual approaches
Sign Up to like & getrecommendations! Published in 2021 at "Journal of Molecular Structure"
DOI: 10.1016/j.molstruc.2021.130156
Abstract: Abstract A new unexpected hybrid based on the arylidene-thiazolidinone and 1,3,4-thiadiazole scaffolds via combined S-alkylation and Smiles rearrangement dual protocols. The one-pot reaction of arylidene-thiazolidinone with the hydrazonoyl chloride in a basic medium (Et3N) with… read more here.
Keywords: alkylation smiles; smiles rearrangement; rearrangement dual; structure ... See more keywords
Access to ortho-Hydroxyphenyl Ketimines via Imine Anion-Mediated Smiles Rearrangement.
Sign Up to like & getrecommendations! Published in 2022 at "Organic letters"
DOI: 10.1021/acs.orglett.2c01349
Abstract: We have achieved a facile access to N-(2-halophenyl)-2-hydroxyphenylimine derivatives via imine anion-mediated Smiles rearrangement. When 2-(2-halophenoxy)benzonitriles were treated with 1.2-1.4 equiv of organolithium reagents, nucleophilic addition to the nitrile group followed by Smiles rearrangement occurred… read more here.
Keywords: smiles rearrangement; imine anion; anion mediated; access ... See more keywords
Electrochemical Reductive Smiles Rearrangement for C-N Bond Formation.
Sign Up to like & getrecommendations! Published in 2019 at "Organic letters"
DOI: 10.1021/acs.orglett.8b03178
Abstract: A conceptually new and synthetically valuable radical Smiles rearrangement reaction is reported under undivided electrolytic conditions. This protocol employs an entirely new strategy for the electrochemical radical Smiles rearrangement. Remarkably, an amidyl radical generated from… read more here.
Keywords: rearrangement bond; bond formation; bond; electrochemical reductive ... See more keywords
Switchable Smiles Rearrangement for Enantioselective O-Aryl Amination.
Sign Up to like & getrecommendations! Published in 2019 at "Organic letters"
DOI: 10.1021/acs.orglett.9b01848
Abstract: Asymmetric assembly of atropisomeric anilines from abundant and readily available precursors is one of the most challenging but valuable processes in organic synthesis. The use of highly efficient Smiles rearrangement to accomplish switchable enantioselective amination… read more here.
Keywords: switchable smiles; enantioselective aryl; aryl amination; amination ... See more keywords
Synthesis of Various 2-Aminobenzoxazoles: The Study of Cyclization and Smiles Rearrangement
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DOI: 10.1021/acsomega.9b02702
Abstract: This study reports two synthetic approaches leading to 2-aminobenzoxazoles and their N-substituted analogues. Our first synthetic strategy involves a reaction between various o-aminophenols and N-cyano-N-phenyl-p-toluenesulfonamide as a nonhazardous electrophilic cyanating agent in the presence of… read more here.
Keywords: cyclization smiles; synthesis various; aminobenzoxazoles study; various aminobenzoxazoles ... See more keywords
Unexpected Gas-Phase Nitrogen-Oxygen Smiles Rearrangement: Collision-Induced Dissociation of Deprotonated 2-(N-Methylanilino)ethanol and Morpholinylbenzoic Acid Derivatives.
Sign Up to like & getrecommendations! Published in 2022 at "Journal of the American Society for Mass Spectrometry"
DOI: 10.1021/jasms.2c00210
Abstract: A nitrogen-oxygen Smiles rearrangement was reported to occur after collisional activation of the PhN(R)CH2CH2O- (R = alkyl) anion, which undergoes a five-membered ring rearrangement to form a phenoxide ion C6H5O-. When R = H, such… read more here.
Keywords: nitrogen oxygen; smiles rearrangement; phenoxide ion; oxygen ... See more keywords
A visible light-mediated, decarboxylative, desulfonylative Smiles rearrangement for general arylethylamine syntheses.
Sign Up to like & getrecommendations! Published in 2020 at "Chemical communications"
DOI: 10.1039/d0cc05049k
Abstract: A decarboxylative, desulfonylative Smiles rearrangement is presented that employs activated-ester/energy transfer catalysis to decarboxylate β-amino acid derived starting materials at room-temperature under visible light irradiation. The radical Smiles rearrangement gives a range of biologically active… read more here.
Keywords: arylethylamine; desulfonylative smiles; light mediated; visible light ... See more keywords