(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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Bibliographic Details
Published in	Tetrahedron Vol. 67; no. 1; pp. 167 - 172
Main Authors	Giomi, Donatella, Alfini, Renzo, Brandi, Alberto
Format	Journal Article
Language	English
Published	OXFORD Elsevier Ltd 07.01.2011 Elsevier
Subjects	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 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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ISSN	0040-4020 1464-5416
DOI	10.1016/j.tet.2010.11.008

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Summary:	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]
Bibliography:	http://dx.doi.org/10.1016/j.tet.2010.11.008 ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	0040-4020 1464-5416
DOI:	10.1016/j.tet.2010.11.008