Chemie der Cumalinsäurederivate. I. Synthese und  Diels‐Alder ‐Reaktionen von 1‐Arylamino‐2‐methoxycarbonylbutadienen | Zendy

Kvita Vratislav | Zendy; Sauter Hanspeter | Zendy; Rihs Grete | Zendy

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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.

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