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1-Chloroalkyl-, 1-(2,2-dichloroalkyl)-, and 1-(trichloromethyl)-3,4-dihydroisoquinolines are synthesized by chlorination of 1-alkyl-3,4-dihydroisoquinolines with N-chlorosuccinimide. These novel chlorinated 3,4-dihydroisoquinolines are suitable precursors for functionalized isoquinolines by aromatization involving sequential 1,4-dehydrochlorination, tautomerization, and nucleophilic substitution.
3-Chloro- and 3-bromo-2-arylpyrroles, which are potential physiologically active compounds in agrochemistry and pharmaceutical sciences, were efficiently prepared from the corresponding 2-aryl-1-pyrrolines by α,α-dihalogenation with N-halosuccinimides and subsequent base-induced monodehydrohalogenation using sodium methoxide in methanol.
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