Benzotriazole and its 5-methyl- and 5-nitro derivatives react with diethyl ethoxymethylenemalonate by ethylation at each of the ring N-atoms and through Michael addition, to give the isomeric esters ethyl (E/Z) 3[5(6)-R-benzotriazol-1-yl]propenoates. Benzotriazole and its 5-nitro derivative react similarly with ethyl acetoacetate but N-ethyl derivatives are obtained in lower yields. Other 1,2,3-triazoles derivatives and indole were ineffective in this reaction while benzimidazole produced similar results but accompanied with a small amount of a benzimidazoline addition product, whose structure has been determined by crystallographic analysis.
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|Titolo:||Reactions of Benzotriazoles with Diethyl Ethoxymethylenemalonate; Ethylation and Michael Addition. Comparison with Other Esters and W-Heterocycles|
|Autori interni:||CARTA, Antonio|
|Data di pubblicazione:||1997|
|Rivista:||JOURNAL OF HETEROCYCLIC CHEMISTRY|
|Appare nelle tipologie:||1.1 Articolo in rivista|