scholarly journals Experimental and Computational Studies of Microwave-Assisted, Facile Ring Opening of Epoxide with Less Reactive Aromatic Amines in Nitromethane

ACS Omega ◽  
2020 ◽  
Vol 5 (30) ◽  
pp. 18746-18757
Author(s):  
Sumit Kumar ◽  
Charu Upadhyay ◽  
Meenakshi Bansal ◽  
Maria Grishina ◽  
Bhupender S. Chhikara ◽  
...  
Keyword(s):  
Aromatic Amines ◽  
Ring Opening ◽  
Computational Studies ◽  
Microwave Assisted ◽  
Ring Opening Of Epoxide

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>

ChemInform Abstract: An Efficient Method for the Ring Opening of Epoxide with Aromatic Amines by Sb(III) Chloride under Microwave Irradiation.

ChemInform ◽  
2008 ◽  
Vol 39 (41) ◽  
Author(s):  
Dadkhoda Ghazanfari ◽  
Mohammed M. Hashemi ◽  
Mohammad Mehdi Mottaghi ◽  
Mohammad Mehdi Foroughi
Keyword(s):  
Microwave Irradiation ◽  
Efficient Method ◽  
Aromatic Amines ◽  
Ring Opening ◽  
Ring Opening Of Epoxide

Microwave-assisted asymmetric ring opening of meso-epoxides with aromatic amines catalyzed by a Ti-S-(−)-BINOL complex

2006 ◽  
Vol 47 (30) ◽  
pp. 5277-5279 ◽  
Author(s):  
Rukhsana I. Kureshy ◽  
Surendra Singh ◽  
Noor-ul H. Khan ◽  
Sayed H.R. Abdi ◽  
Santosh Agrawal ◽  
...  
Keyword(s):  
Aromatic Amines ◽  
Ring Opening ◽  
Microwave Assisted ◽  
Asymmetric Ring Opening

Microwave-Assisted Asymmetric Ring Opening of meso-Epoxides with Aromatic Amines Catalyzed by a Ti—(S)-(-)-BINOL Complex.

ChemInform ◽  
2006 ◽  
Vol 37 (45) ◽  
Author(s):  
Rukhsana I. Kureshy ◽  
Surendra Singh ◽  
Noor-ul H. Khan ◽  
Sayed H. R. Abdi ◽  
Santosh Agrawal ◽  
...  
Keyword(s):  
Aromatic Amines ◽  
Ring Opening ◽  
Microwave Assisted ◽  
Asymmetric 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>

Reactions of 4-Pyrones with Azomethine Ylides as a Chemo­selective Method for the Construction of Multisubstituted Pyrano[2,3-c]pyrrolidines

Synthesis ◽  
2021 ◽  
Author(s):  
Dmitrii L. Obydennov ◽  
Vyacheslav D. Steben’kov ◽  
Konstantin L. Obydennov ◽  
Sergey A. Usachev ◽  
Vladimir S. Moshkin ◽  
...  
Keyword(s):  
Double Bond ◽  
Ring Opening ◽  
Azomethine Ylides ◽  
Azomethine Ylide ◽  
Dipolar Cycloaddition ◽  
Computational Studies ◽  
Carbon Double Bond ◽  
Reactivity Indexes ◽  
Reaction Proceeds

Abstract4-Pyrones bearing electron-donating and electron-withdrawing groups react with nonstabilized azomethine ylides to form pyrano[2,3-c]pyrrolidines in moderate to good yields. The reaction proceeds chemoselectively as a 1,3-dipolar cycloaddition of the azomethine ylide at the carbon–carbon double bond of the pyrone activated by the electron-withdrawing substituent. The reactivity of 4-pyrones toward azomethine ylides was rationalized by computational studies with the use of reactivity indexes. The pyrano[2,3-c]pyrrolidine moiety could be modified, for example by a ring-opening transformation under the action of hydrazine to provide pyrazolyl-substituted pyrrolidines.

LiClO4-Catalyzed Ring-Opening of Aziridines with Aromatic Amines

Synlett ◽  
2002 ◽  
Vol 2002 (01) ◽  
pp. 0053-0056 ◽  
Author(s):  
J. S. Yadav ◽  
B. V. S. Reddy ◽  
B. Jyothirmai ◽  
M. S. R. Murty
Keyword(s):  
Aromatic Amines ◽  
Ring Opening

Samarium Iodides Catalyzed meso-Epoxides Ring Opening by Aromatic Amines.

ChemInform ◽  
2005 ◽  
Vol 36 (4) ◽  
Author(s):  
Fabien Carree ◽  
Richard Gil ◽  
Jacqueline Collin
Keyword(s):  
Aromatic Amines ◽  
Ring Opening
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