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

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-(N-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.

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

ACS Omega ◽

10.1021/acsomega.0c01760 ◽

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

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ChemInform Abstract: An Efficient Method for the Ring Opening of Epoxides with Aromatic Amines Catalyzed by Indium Trichloride.

ChemInform ◽

10.1002/chin.200124101 ◽

2010 ◽

Vol 32 (24) ◽

pp. no-no

Author(s):

L. Rajender Reddy ◽

M. Arjun Reddy ◽

N. Bhanumathi ◽

K. Rama Rao

Keyword(s):

Efficient Method ◽

Aromatic Amines ◽

Ring Opening ◽

Ring Opening Of Epoxides

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An efficient method for regioselective ring opening of epoxides by amines under microwave irradiation using Bi(NO3)3·5H2O as a catalyst

New Journal of Chemistry ◽

10.1039/c6nj03701a ◽

2017 ◽

Vol 41 (7) ◽

pp. 2668-2671 ◽

Cited By ~ 6

Author(s):

Shobha Bansal ◽

Yogendra Kumar ◽

Parveen Pippal ◽

Dipak K. Das ◽

Panchanan Pramanik ◽

...

Keyword(s):

Microwave Irradiation ◽

Efficient Method ◽

Ring Opening ◽

Amino Alcohols ◽

Solvent Free ◽

Environmentally Benign ◽

Highly Efficient ◽

Ring Opening Of Epoxides ◽

Nucleophilic Ring Opening

Bi(NO3)3·5H2O a highly efficient environmentally benign catalyst, is used for the nucleophilic ring opening of epoxides with aromatic, aliphatic and heteroaromatic amines under solvent free microwave conditions to afford the corresponding β-amino alcohols in good to excellent yields with high regioselectivity.

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

10.26434/chemrxiv.12022908.v1 ◽

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

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-(N-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.

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An Efficient Method for the Ring Opening of Epoxides with Aromatic Amines Catalyzed by Bismuth Trichloride.

ChemInform ◽

10.1002/chin.200303074 ◽

2003 ◽

Vol 34 (3) ◽

Author(s):

Thierry Ollevier ◽

Guillaume Lavie-Compin

Keyword(s):

Efficient Method ◽

Aromatic Amines ◽

Ring Opening ◽

Ring Opening Of Epoxides

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Microwave Irradiation Syntheses and Crystal Structures of Two Series of Novel Fivemembered Heterocyclic Mono-Imine Compounds

Current Organic Synthesis ◽

10.2174/1570179416666181207125604 ◽

2019 ◽

Vol 16 (3) ◽

pp. 444-448 ◽

Cited By ~ 1

Author(s):

Biyun Su ◽

Yaning Li ◽

Dandan Pan ◽

Paison Faida ◽

Tingyu Yan ◽

...

Keyword(s):

Microwave Irradiation ◽

Aromatic Amines ◽

Imine Group ◽

Polymerization Catalysis ◽

Elementary Analysis ◽

Toluene Sulfonic Acid ◽

Ft Ir ◽

Coordination Ability ◽

Imine Compounds ◽

Late Transition

Aim and Objective: The late transition metal complexes with five-membered heterocyclic mono-imine ligands have attracted much attention because of their potential application in olefin polymerization catalysis. In order to increase the coordination ability of heteroatom N and S to center metals, CH3 group was introduced into the side arm of pyrrole imine and thiophene imine respectively, to get two series of novel five-membered heterocyclic imine compounds, mono(imino)pyrroles and mono(imino)thiophenes Materials and Methods: Two series of novel five-membered heterocyclic compounds with the mono-imine group were synthesized from the p-toluene sulfonic acid catalyzed Schiff base condensation of aromatic amines and 2-acetylpyrrole/ 2-acetylthiophene respectively, using CH3 group to substitute the common H atom on the side arm of pyrrole imine/ thiophene imine. Results: All the heterocyclic mono-imine compounds were characterized adequately by means of 1H NMR, 13C NMR, FT-IR, elementary analysis, as well as X-ray crystallographic diffraction. The reactivity differences between two precursor 2-acetylpyrrole and 2-acetylthiophene with aromatic amines were compared and discussed in detail. Conclusion: Compared to traditional heating methods, the solvent-free microwave irradiation seemed more efficient to prepare these series of five-membered heterocyclic mono-imine compounds, which resulted in a higher yield and cleaner product.

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