14529-53-4Relevant articles and documents
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Kornblum,Coffey
, p. 3447 (1966)
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Newbold,Spring
, p. 1864 (1948)
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Novel synthesis method for ortho-alkane superseded pyridine
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Paragraph 0018; 0019; 0020; 0021, (2017/07/19)
The invention relates to a novel synthesis method for ortho-alkane superseded pyridine. According to the method, ortho halogenated pyridine serves as raw materials, the ortho halogenated pyridine and corresponding alcohol react to obtain the ortho-alkane superseded pyridine under the action of sodium hydroxide. The reaction has universality for the ortho halogenated pyridine, and the method is simple and practical. Influence of consumption of the sodium hydroxide on mono-substitution and di-substitution in the reaction is inspected, alkoxy mono-substitution products and alkoxy di-substitution production are acquired, and a novel simply-operated, economical and favorable process for synthesis ortho-alkane superseded pyridine is provided.
NaBH4-TMEDA and a palladium catalyst as efficient regio- and chemoselective system for the hydrodehalogenation of halogenated heterocycles
Chelucci, Giorgio,Figus, Susanna
, p. 191 - 209 (2014/07/21)
The pair NaBH4-TMEDA as hydride source and a palladium catalyst in THF prove to be an efficient system for the hydrodehalogenation of halogenated heterocycles with one or more heteroatoms. In general, Pd(OAc) 2-PPh3 rapidly hydrodehalogenates reactive halo-heterocycles such as bromo-pyridines, -quinolines, -thiophenes, -indoles, -imidazoles, etc., at room temperature in very good yields, whereas in most cases PdCl2(dppf) reduces less reactive halides such as chloro-pyridines, -quinolines, -pyrimidines and bromo-indoles, -benzofurans, etc. Moreover, PdCl2(tbpf) shows to be even more active removing the 2- and 5-chlorine from both thiophene and thiazole rings. The reaction conditions tolerate various functional groups, allowing highly chemoselective reactions in the presence of halide, ester, alkyne, alkene and nitrile substituents. Moreover, with a proper selection of the catalyst it is also possible to obtain a good control in the regioselective hydrodehalogenation of a variety of polyhalogenated substrates.
