scholarly journals Biocatalytic Aromaticity-Breaking Epoxidation of Naphthalene and Nucleophilic Ring-Opening Reactions

ACS Catalysis ◽  
2021 ◽  
Vol 11 (5) ◽  
pp. 2644-2649 ◽  
Author(s):  
Wuyuan Zhang ◽  
Huanhuan Li ◽  
Sabry H. H. Younes ◽  
Patricia Gómez de Santos ◽  
Florian Tieves ◽  
...  
Keyword(s):  
Ring Opening ◽  
Ring Opening Reactions ◽  
Nucleophilic Ring Opening

ChemInform Abstract: SYNTHESIS AND NUCLEOPHILIC RING-OPENING REACTIONS OF ACTIVATED BICYCLO(3.1.0)HEXANES

1977 ◽  
Vol 8 (10) ◽  
pp. no-no
Author(s):  
K. KONDO ◽  
E. HIRO ◽  
D. TUNEMOTO
Keyword(s):  
Ring Opening ◽  
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.

Understanding the Unusual Regioselectivity in the Nucleophilic Ring-Opening Reactions ofgem-Disubstituted Cyclic Sulfates. Experimental and Theoretical Studies

2003 ◽  
Vol 68 (11) ◽  
pp. 4506-4513 ◽  
Author(s):  
Alberto Avenoza ◽  
Jesús H. Busto ◽  
Francisco Corzana ◽  
José I. García ◽  
Jesús M. Peregrina
Keyword(s):  
Ring Opening ◽  
Theoretical Studies ◽  
Ring Opening Reactions ◽  
Cyclic Sulfates ◽  
Experimental And Theoretical Studies ◽  
Nucleophilic Ring Opening

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: Stereochemistry of Nucleophilic Ring-Opening Reactions of Optically Active N-Acetyl-2-methoxycarbonylaziridine.

ChemInform ◽  
2010 ◽  
Vol 27 (1) ◽  
pp. no-no
Author(s):  
P. DAVOLI ◽  
A. FORNI ◽  
I. MORETTI ◽  
F. PRATI
Keyword(s):  
Ring Opening ◽  
Optically Active ◽  
Ring Opening Reactions ◽  
Nucleophilic Ring Opening

Nucleophilic ring-opening reactions of morpholin-2-ones. A resolution of dl-(secondary-alkyl)amines

1989 ◽  
Vol 54 (4) ◽  
pp. 789-792 ◽  
Author(s):  
Choji Kashima ◽  
Kazuo Harada
Keyword(s):  
Ring Opening ◽  
Alkyl Amines ◽  
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

Regioselective nucleophilic ring opening reactions of 2,2-disubstituted aziridines — the asymmetric synthesis of α,α-disubstituted amino acids

Tetrahedron ◽  
1996 ◽  
Vol 52 (40) ◽  
pp. 13035-13050 ◽  
Author(s):  
Beatrice G.M. Burgaud ◽  
David C. Horwell ◽  
Allessandro Padova ◽  
Martyn C. Pritchard
Keyword(s):  
Amino Acids ◽  
Asymmetric Synthesis ◽  
Ring Opening ◽  
Ring Opening Reactions ◽  
Disubstituted Amino Acids ◽  
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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