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

New and stable ethyl 1,2-disubstituted 1,2-dihydroisoquinoline-3-carboxylates 6 and 12a 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 directl...

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Bibliographic Details
Published inSynlett no. 11; pp. 1703 - 1706
Main Authors Meziane, MAA, Bazureau, JP
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 2001
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
solvent-free quaternization
Grignard reaction
1,2-dihydroisoquinoline
ACID
lipophilic isoquinolinium salt
ionic methathesis
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Summary:New and stable ethyl 1,2-disubstituted 1,2-dihydroisoquinoline-3-carboxylates 6 and 12a 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-3carboxylates 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 perfuorobutanesulfonates 4 and 11a by ionic metathesis.
ISSN:0936-5214
DOI:10.1055/s-2001-18079