Tetrahedron

Synthesis of 2-acyl-3-chloropyrroles: application to the synthesis of the trail pheromone of the ant Atta texana

KA Tehrani, D Borremans, N De Kimpe

文献索引：Tehrani, Kourosch Abbaspour; Borremans, Didier; De Kimpe, Norbert Tetrahedron, 1999 , vol. 55, # 13 p. 4133 - 4152

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被引用次数: 23

摘要

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 ...