Tetrahedron p. 4133 - 4152 (1999)
Update date:2022-08-11
Topics:
Tehrani, Kourosch Abbaspour
Borremans, Didier
De Kimpe, Norbert
Alkyl 3-chloropyrrole-2-carboxylates and 2-alkanoyl-3-chloropyrroles are conveniently prepared from 2-alkyl-1-pyrrolines by tetra- and pentahalogenation with N-chlorosuccinimide, subsequent base-induced aromatisation with sodium alkoxides in the corresponding alcohol and final acid hydrolysis of the resulting orthoester or acetal functions into the 3- chloropyrrole. The developed strategy is applied to the synthesis of the trail pheromone of the ant Atta texana.
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