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

doi:10.1055/s-2001-18079

Synlett 2001; 2001(11): 1703-1706
DOI: 10.1055/s-2001-18079

letter

© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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

Abstract

als PDF herunterladen Alle Artikel dieser Rubrik

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.

1,2-dihydroisoquinoline - Grignard reaction - lipophilic isoquinolinium salt - ionic methathesis - solvent-free quaternization

PDF (76 kb)