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Synlett 2001; 2001(11): 1703-1706
DOI: 10.1055/s-2001-18079
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
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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.
1,2-dihydroisoquinoline - Grignard reaction - lipophilic isoquinolinium salt - ionic methathesis - solvent-free quaternization