Synlett 2001; 2001(11): 1703-1706
DOI: 10.1055/s-2001-18079
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Regioselective Addition of Grignard Reagents to New Lipophilic Isoquinolinium Salts Applied to the Synthesis of Stable Ethyl 1,2-disubstituted 1,2-Dihydroisoquinoline-3-carboxylates and Derivatives

Mohamed Aït Amer Meziane* , Jean Pierre Bazureau
  • *Université de Rennes 1, Institut de Chimie, Synthèse & Electrosynthèse Organiques 3, UMR 6510, Bât. 10A, Campus de Beaulieu, Avenue du Général Leclerc, CS 74205, 35042 Rennes Cedex, France; Fax + 33(299)28 63 74; E-mail: jean-pierre.bazureau@univ-rennes1.fr
Further Information

Publication History

Publication Date:
29 October 2001 (online)

New and stable ethyl 1,2-disubstituted 1,2-dihydroisoquinoline-3-carboxylates 6 and 12 a were synthesized in good yields by regioselective addition reactions of alkyl Grignard reagents to lipophilic and soluble isoquinolinium salts 4 and 11. The salts 4 and 11 were obtained quantitatively and directly from isoquinoline-3-carboxylates 1(a,b) with the corresponding alkyl halides 2 or symmetric alkyl dihalides 7 using solventless quaternization reaction conditions and were converted into the corresponding isoquinolinium perfluorobutanesulfonates 4 and 11 a by ionic metathesis.