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.

Reactions of Benzotriazoles with Diethyl Ethoxymethylenemalonate; Ethylation and Michael Addition. Comparison with Other Esters and W-Heterocycles / Sanna, P; Carta, Antonio; Paglietti, G.. - In: JOURNAL OF HETEROCYCLIC CHEMISTRY. - ISSN 0022-152X. - 34:97(1997), pp. 97-106.

Reactions of Benzotriazoles with Diethyl Ethoxymethylenemalonate; Ethylation and Michael Addition. Comparison with Other Esters and W-Heterocycles

CARTA, Antonio;
1997-01-01

Abstract

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.
1997
Reactions of Benzotriazoles with Diethyl Ethoxymethylenemalonate; Ethylation and Michael Addition. Comparison with Other Esters and W-Heterocycles / Sanna, P; Carta, Antonio; Paglietti, G.. - In: JOURNAL OF HETEROCYCLIC CHEMISTRY. - ISSN 0022-152X. - 34:97(1997), pp. 97-106.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11388/46942
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