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Molecules ; 20(9): 15797-806, 2015 Aug 31.
Artigo em Inglês | MEDLINE | ID: mdl-26334262

RESUMO

A series of simple 2-methylpyridines were synthesized in an expedited and convenient manner using a simplified bench-top continuous flow setup. The reactions proceeded with a high degree of selectivity, producing α-methylated pyridines in a much greener fashion than is possible using conventional batch reaction protocols. Eight 2-methylated pyridines were produced by progressing starting material through a column packed with Raney(®) nickel using a low boiling point alcohol (1-propanol) at high temperature. Simple collection and removal of the solvent gave products in very good yields that were suitable for further use without additional work-up or purification. Overall, this continuous flow method represents a synthetically useful protocol that is superior to batch processes in terms of shorter reaction times, increased safety, avoidance of work-up procedures, and reduced waste. A brief discussion of the possible mechanism(s) of the reaction is also presented which involves heterogeneous catalysis and/or a Ladenberg rearrangement, with the proposed methyl source as C1 of the primary alcohol.


Assuntos
Técnicas de Química Sintética/instrumentação , Técnicas de Química Sintética/métodos , Piridinas/síntese química , Catálise , Metilação , Estrutura Molecular , Picolinas/síntese química , Picolinas/química , Piridinas/química
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