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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

✍ Scribed by K. Schenker; J. Druey

Publisher
John Wiley and Sons
Year
1959
Tongue
German
Weight
257 KB
Volume
42
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

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.

📜 SIMILAR VOLUMES

Heilmittelchemische Studien in der heter
Heilmittelchemische Studien in der heterocyclischen Reihe. 29. Mitteilung. Hydropyridine III. Die Anlagerung von Phenylacetonitril an 1-Methyl-3-cyan-1,6-dihydro-pyridin
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## Abstract It has been shown that the reaction between kojic acid and hydrazine hydrate gives rise to two main products: 3,6‐dihydroxymethyl‐4‐oxo‐1,4‐dihydro‐pyridazine, and the hydrazone of 3‐hydroxymethyl‐pyrazol‐5‐yl‐hydroxyacetaldehyde, the structures of which were proved unambiguously.