(2-Pyridyl)phenyl methanol: a new reagent for metal-free reduction of nitro aromatic compounds
As previously reported for 1-(2-pyridyl)-2-propen-1-ol, (2-pyridyl)phenyl methanol is able to react as hydrogen donor towards nitro aromatic and heteroaromatic compounds. Operating in the presence of methyl acrylate as an aza-Michael acceptor, a domino process involving reduction and conjugate addit...
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Published in | Tetrahedron Vol. 67; no. 1; pp. 167 - 172 |
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Main Authors | , , |
Format | Journal Article |
Language | English |
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07.01.2011
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ISSN | 0040-4020 1464-5416 |
DOI | 10.1016/j.tet.2010.11.008 |
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Abstract | As previously reported for 1-(2-pyridyl)-2-propen-1-ol, (2-pyridyl)phenyl methanol is able to react as hydrogen donor towards nitro aromatic and heteroaromatic compounds. Operating in the presence of methyl acrylate as an aza-Michael acceptor, a domino process involving reduction and conjugate addition steps allows the one pot formation of β-amino esters. The crucial role of the pyridine nucleus in making this purely thermal reactivity of carbinols possible has been shown.
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AbstractList | As previously reported for 1-(2-pyridyl)-2-propen-1-ol, (2-pyridyl)phenyl methanol is able to react as hydrogen donor towards nitro aromatic and heteroaromatic compounds. Operating in the presence of methyl acrylate as an aza-Michael acceptor, a domino process involving reduction and conjugate addition steps allows the one pot formation of β-amino esters. The crucial role of the pyridine nucleus in making this purely thermal reactivity of carbinols possible has been shown.
[Display omitted] As previously reported for 1-(2-pyridyl)-2-propen-1-ol, (2-pyridyl)phenyl methanol is able to react as hydrogen donor towards nitro aromatic and heteroaromatic compounds. Operating in the presence of methyl acrylate as an aza-Michael acceptor, a domino process involving reduction and conjugate addition steps allows the one pot formation of beta -amino esters. The crucial role of the pyridine nucleus in making this purely thermal reactivity of carbinols possible has been shown. As previously reported for 1-(2-pyridyl)-2-propen-1-ol, (2-pyridyl)phenyl methanol is able to react as hydrogen donor towards nitro aromatic and heteroaromatic compounds. Operating in the presence of methyl acrylate as an aza-Michael acceptor, a domino process involving reduction and conjugate addition steps allows the one pot formation of beta-amino esters. The crucial role of the pyridine nucleus in making this purely thermal reactivity of carbinols possible has been shown. (C) 2010 Elsevier Ltd. All rights reserved. As previously reported for 1-(2-pyridyl)-2-propen-1-ol, (2-pyridyl)phenyl methanol is able to react as hydrogen donor towards nitro aromatic and heteroaromatic compounds. Operating in the presence of methyl acrylate as an aza-Michael acceptor, a domino process involving reduction and conjugate addition steps allows the one pot formation of β-amino esters. The crucial role of the pyridine nucleus in making this purely thermal reactivity of carbinols possible has been shown. |
Author | Giomi, Donatella Alfini, Renzo Brandi, Alberto |
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Keywords | Hantzsch ester 1,4-dihydropyridine mimics UYESUYBXKHPUDU-UHFFFAOYSA-N Pyridyl carbinols Nitro derivatives Metal-free reductions GCSHUYKULREZSJ-UHFFFAOYSA-N 1-(2-PYRIDYL)-2-PROPEN-1-OL ACIDS TRANSFER HYDROGENATION ALDEHYDES HANTZSCH ESTERS N-OXIDES CHEMISTRY DIHYDROPYRIDINES ASYMMETRIC ORGANOCATALYSIS DERIVATIVES Acrylic acid ester Michael addition One pot reaction Nitro compound Chemical reagent Nitrogen heterocycle Thermal reaction Pyridine derivatives Chemical reduction Aminoester Addition reaction Aromatic compound Dihydropyridine derivatives Electron acceptor Ethylenic compound Electron donor Methanol Successive reaction |
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Snippet | As previously reported for 1-(2-pyridyl)-2-propen-1-ol, (2-pyridyl)phenyl methanol is able to react as hydrogen donor towards nitro aromatic and heteroaromatic... |
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SubjectTerms | Aromatic compounds chemical reduction Chemistry Chemistry, Organic Conjugates Esters Exact sciences and technology Hantzsch ester 1,4-dihydropyridine mimics Heteroaromatic compounds Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives hydrogen Metal-free reductions methanol Methyl alcohol Nitro derivatives Organic chemistry Physical Sciences Preparations and properties Pyridines Pyridyl carbinols Reduction Science & Technology synthesis Tetrahedrons |
Title | (2-Pyridyl)phenyl methanol: a new reagent for metal-free reduction of nitro aromatic compounds |
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