Journal of Heterocyclic Chemistry p. 97 - 106 (1997)
Update date:2022-08-03
Topics:
Sanna, Paolo
Carta, Antonio
Paglietti, Giuseppe
Bacchi, Alessia
Pelizzi, Giancarlo
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 detenruned by crystallographic analysis.
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