A highly effective synthesis of haloalkylidene-substituted heterocycles by copper(II)-catalyzed cyclization of alkynyl ureas and secondary amides has been developed. The reaction, which involves a catalytic amount of CuCl2 and a stoichiometric amount of N-halosuccinimide, occurs selectively through an alkoxyhalogenation process. Alternatively, alkoxychlorination and alkoxybromination reactions can be performed working solely with stoichiometric CuCl, and CuBr2, respectively.

Copper(II)-catalyzed alkoxyhalogenation of alkynyl ureas and amides as a route to haloalkylidene substituted heterocycles

Gazzola, S.;BROGGINI, GIANLUIGI
2015-01-01

Abstract

A highly effective synthesis of haloalkylidene-substituted heterocycles by copper(II)-catalyzed cyclization of alkynyl ureas and secondary amides has been developed. The reaction, which involves a catalytic amount of CuCl2 and a stoichiometric amount of N-halosuccinimide, occurs selectively through an alkoxyhalogenation process. Alternatively, alkoxychlorination and alkoxybromination reactions can be performed working solely with stoichiometric CuCl, and CuBr2, respectively.
2015
GOLD-CATALYZED CYCLOISOMERIZATION; ACTIVATION/C-O CYCLIZATION; EFFICIENT SYNTHESIS; INTRAMOLECULAR HYDROALKOXYLATION; BOND FORMATION; STEREOCONTROLLED SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; CARBOAMINATION REACTIONS; ALKENE CARBOAMINATION; 2,3-OR 3,4-ALLENOLS
Gazzola, S.; Beccalli, E. M.; Borelli, T.; Castellano, C.; Chiacchio, M. A.; Diamante, D.; Broggini, Gianluigi
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11383/2022761
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