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Benzylidène-5-hydroxy-4-dihydro-2,5-thiophènecarboxanilides-3-(Z): Synthèse et isomérisation en benzyl-5-hydroxy-4-thiophènecarboxanilides-3

✍ Scribed by Roland Jaunin

Publisher
John Wiley and Sons
Year
1980
Tongue
German
Weight
694 KB
Volume
63
Category
Article
ISSN
0018-019X

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✦ Synopsis

(Z)‐5‐Benzylidene‐2,5‐dihydro‐4‐hydroxy‐3‐thiophenecarboxanilides: Synthesis and Isomerization into 5‐Benzyl‐4‐hydroxy‐3‐thiophenecarboxanilides

Upon treatment with an arylamine in boiling xylene, the esters I yield predominantly the corresponding anilides II, along with a small but variable amount of the isomeric thiophene derivatives III (Table 1). On the other hand, the derivatives III can be readily prepared by base‐ or acid‐catalyzed isomerization of II. Esters I can also be isomerized to the corresponding thiophene derivatives IV (Scheme 6), but only in the presence of a strong acid (Table 4). The two series of isomers reported in Tables 2 and 3 present spectral differences which allow unambiguous structural assignments. The (Z)‐configuration for compounds of Table 2 is confirmed by a NOE study carried out on the O‐methyl derivatives 6a and 7a.

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