Title
Synthesis of 2-acyl-3-chloropyrroles : application to the synthesis of the trail pheromone of the ant **Atta texana** Synthesis of 2-acyl-3-chloropyrroles : application to the synthesis of the trail pheromone of the ant **Atta texana**
Author
Faculty/Department
Faculty of Sciences. Chemistry
Publication type
article
Publication
Oxford ,
Subject
Chemistry
Source (journal)
Tetrahedron. - Oxford
Volume/pages
55(1999) :13 , p. 4133-4152
ISSN
0040-4020
ISI
000079403800029
Carrier
E
Target language
English (eng)
Abstract
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 texnna. (C) 1999 Elsevier Science Ltd. All rights reserved.
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