scholarly journals Intramolecular π−π Stacking Interactions in 2-SubstitutedN,N-Dibenzylaziridinium Ions and Their Regioselectivity in Nucleophilic Ring-Opening Reactions

2010 ◽  
Vol 75 (3) ◽  
pp. 885-896 ◽  
Author(s):  
Saron Catak ◽  
Matthias D’hooghe ◽  
Norbert De Kimpe ◽  
Michel Waroquier ◽  
Veronique Van Speybroeck
Keyword(s):  
Ring Opening ◽  
Stacking Interactions ◽  
Π Stacking ◽  
Ring Opening Reactions ◽  
Nucleophilic Ring Opening

scholarly journals Microwave Heating Promotes the S-Alkylation of Aziridine Catalyzed by Molecular Sieves: A Post-Synthetic Approach to Lanthionine-Containing Peptides

Molecules ◽  
2021 ◽  
Vol 26 (20) ◽  
pp. 6135
Author(s):  
Valentina Verdoliva ◽  
Giuseppe Digilio ◽  
Michele Saviano ◽  
Stefania De Luca
Keyword(s):  
Microwave Irradiation ◽  
Molecular Sieves ◽  
Ring Opening ◽  
Cysteine Residue ◽  
Biologically Active ◽  
Synthetic Approach ◽  
Stepwise Approach ◽  
Valuable Alternative ◽  
Ring Opening Reactions ◽  
Nucleophilic Ring Opening

Aziridine derivatives involved in nucleophilic ring-opening reactions have attracted great interest, since they allow the preparation of biologically active molecules. A chemoselective and mild procedure to convert a peptide cysteine residue into lanthionine via S-alkylation on aziridine substrates is presented in this paper. The procedure relies on a post-synthetic protocol promoted by molecular sieves to prepare lanthionine-containing peptides and is assisted by microwave irradiation. In addition, it represents a valuable alternative to the stepwise approach, in which the lanthionine precursor is incorporated into peptides as a building block.

Nucleophilic ring opening reactions of aziridines

2018 ◽  
Vol 22 (2) ◽  
pp. 447-501 ◽  
Author(s):  
Rabia Akhtar ◽  
Syed Ali Raza Naqvi ◽  
Ameer Fawad Zahoor ◽  
Sameera Saleem
Keyword(s):  
Ring Opening ◽  
Ring Opening Reactions ◽  
Nucleophilic Ring Opening

ChemInform Abstract: Ruthenium-Catalyzed Nucleophilic Ring-Opening Reactions of 7-Oxabenzonorbornadienes with Methanol.

ChemInform ◽  
2013 ◽  
Vol 44 (29) ◽  
pp. no-no
Author(s):  
Kelsey Jack ◽  
Elisabeth Fatila ◽  
Colleen Hillis ◽  
William Tam
Keyword(s):  
Ring Opening ◽  
Ring Opening Reactions ◽  
Nucleophilic Ring Opening

Catalyst Free, Nitromethane Assisted Facile Ring Opening of Epoxide with Less Reactive Aromatic Amines

2020 ◽  
Author(s):  
Sumit Kumar ◽  
Meenakshi Bansal ◽  
Charu Upadhyay ◽  
Maria Grishina ◽  
Vladimir Potemkin ◽  
...  
Keyword(s):  
Aromatic Amines ◽  
Ring Opening ◽  
Spectroscopic Studies ◽  
Bioactive Scaffolds ◽  
Chemistry Research ◽  
Ring Opening Reactions ◽  
Ring Opening Of Epoxide ◽  
Sterically Hindered ◽  
First Time ◽  
Nucleophilic Ring Opening

<p>Nucleophilic ring opening reactions of epoxides with aromatic amines are in the forefront of the synthetic organic chemistry research to build new bioactive scaffolds. Here, a convenient, green and highly efficient regioselective ring opening of sterically hindered (2R,3S)-3-(<i>N</i>-Boc-amino)-1-oxirane-4-phenylbutane with various poorly reactive aromatic amines are accomplished under microwave irradiation in nitromethane. All the reactions effectively implemented for various aromatic amines involves reuse of nitromethane that supports its dual role as a solvent and catalyst. The corresponding new β-alcohol analogs of hydroxyethylamine (HEA) are isolated in 41-98% yields. The reactions proceed under mild conditions for a broad range of less reactive and sterically hindered aromatic amines. Proton NMR and UV-visible spectroscopic studies suggest that the nucleophilicity of amines is influenced by nitromethane, which is substantiated by the extensive computational studies. Overall, this methodology elucidates the first time use of nitromethane as a solvent for the ring opening reactions under microwave conditions involving equimolar ratio of epoxide and aromatic amine without any catalyst, facile ring opening of complex epoxide by less reactive aromatic amines, low reaction time, less energy consumption, recycling of the solvent and simple workup procedures.</p>

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