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Chemie der Cumalinsäurederivate. I. Synthese und Diels‐Alder ‐Reaktionen von 1‐Arylamino‐2‐methoxycarbonylbutadienen
Author(s) -
Kvita Vratislav,
Sauter Hanspeter,
Rihs Grete
Publication year - 1983
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.19830660845
Subject(s) - chemistry , stereospecificity , ring (chemistry) , nucleophile , diels–alder reaction , regioselectivity , medicinal chemistry , stereochemistry , organic chemistry , catalysis
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.