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Heilmittelchemische Studien in der heterocyclischen Reihe. 28. Mitteilung. Hydropyridine II Die Reaktion von 1‐Methyl‐3‐cyan‐1,6‐dihydro‐pyridin mit Maleinsäureanhydrid
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.19590420627
Subject(s) - chemistry , maleic anhydride , bicyclic molecule , pyridine , adduct , cyan , yield (engineering) , medicinal chemistry , maleic acid , catalysis , polymer chemistry , organic chemistry , copolymer , art , materials science , visual arts , metallurgy , polymer
1‐Methyl‐3‐cyano‐l, 6‐dihydro‐pyridine (III) was allowed to react under mild conditions with maleic anhydride. After acid hydrolysis of the resulting adduct IV, followed by esterification of the dicarboxylic acid V, 2‐methyl‐5,6‐dicarbomethoxy‐7‐cyano‐2‐aza‐bicyclo[2.2.2]octene‐(7) (VI) was formed in an overall yield of more than 40%. The structure of VI was deduced from its spectral data and its catalytic hydrogenation to l‐methyl‐5,6‐dicarbomethosy‐7‐cyano‐2‐aza‐bicyclo[2.2.2]octane (VII). The DIELS‐ALDER reaction provides unambiguous structural proof for 111.