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Chemie der Cumalinsäurederivate. I. Synthese und Diels-Alder-Reaktionen von 1-Arylamino-2-methoxycarbonylbutadienen

✍ Scribed by Vratislav Kvita; Hanspeter Sauter; Grete Rihs

Publisher
John Wiley and Sons
Year
1983
Tongue
German
Weight
435 KB
Volume
66
Category
Article
ISSN
0018-019X

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✦ Synopsis

The nucleophilic attack of substituted anilines at position 6 of methyl coumalate (1) opens the α‐pyrone ring to form 4‐arylamino‐3‐(methoxycarbonyl)butadien‐1‐carboxylic acid 2 (Scheme 1). The latter are easily decarboxylated at room temperature in polar aprotic solvents to 1‐arylamino‐2‐(methoxycarbonyl)butadiene 4 which smoothly undergo regio‐ and stereospecific Diels‐Alder reactions with different dienophiles.

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