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Heilmittelchemische Studien in der heterocyclischen Reihe. 27. Mitteilung Hydropyridine I Die Reduktion von 1‐Methyl‐3‐cyan‐pyridiniumjodid mit Natriumborhydrid
Author(s) -
Schenker K.,
Druey J.
Publication year - 1959
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19590420626
Subject(s) - chemistry , pyridine , pyridinium , medicinal chemistry , methyl iodide , sodium dithionite , sodium borohydride , cyan , iodide , halide , catalysis , organic chemistry , art , visual arts
Reduction of 1‐methyl‐3‐cyano‐pyridinium iodide with excess sodium borohydride has been found to give l‐methyl‐3‐cyano‐l,2,5,6‐tetrahydro‐pyridine (I) and l‐methyl‐3‐cyano‐l,6‐dihydro‐pyridine (II a) in approximately equal yields.The constitution of IIa was deduced by comparison with l‐methyl‐3‐cyano‐1,4‐dihydro‐pyridine (II b), obtained exclusively on treatment of 1‐methyl‐3‐cyano‐pyridinium iodide with sodium dithionite, and by its catalytic hydrogenation to l‐methyl‐3‐cyano‐l,4,5,6‐tetrahydro‐pyridine (III).