1, 4-Dehydrochlorination of 1-(1-haloalkyl)-3, 4-dihydroisoquinolines as a convenient route to functionalized isoquinolines

…, P Markusse, P De Cooman, L Maat, N De Kimpe

Index: Jacobs, Jan; Van, Tuyen Nguyen; Stevens, Christian V.; Markusse, Peter; De Cooman, Paul; Maat, Leendert; De Kimpe, Norbert Tetrahedron Letters, 2009 , vol. 50, # 26 p. 3698 - 3701

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Citation Number: 4

Abstract

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.