Triflate ion-promoted addition reactions of allylsilane to quinolines and isoquinolines acylated by chloroformate esters

Tetrahedron Letters

Volumn 38, Issue 3, 1997, Pages 403-406

  Yamaguchi, Ryohei ^a   Hatano, Bunpei ^a   Nakayasu, Tatsuya ^a   Kozima, Sinpei ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ISOQUINOLINE DERIVATIVE; QUINOLINE DERIVATIVE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; METHODOLOGY; REACTION ANALYSIS;

EID: 0031021708     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02310-6     Document Type: Article

References (16)

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11. (a) Chatgilialoglu, C. Acc. Chem. Res. 1992, 25, 188-194;
12. (b) Chatgilialoglu, C. Chem. Rev. 1995, 95, 1229-1251;
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14. 1H NMR showed new signals at 10.02, 9.34, and 8.75 ppm, probably due to the assumed 5, which disappeared by addition of allyltrimethylsilane to the mixture giving the adduct 3a. This preliminary result should support the plausible reaction pathway shown in Scheme 1.
15. It has been reported that trimethylsilyl triflate promotes the reactions of allyltrimethylsilane with αalkoxyamides. For example, see Bernardi, A.; Micheli, F.; Potenza, D.; Scolastico, C.; Villa, R. Tetrahedron Lett. 1990, 31, 4949-4952.
16. All new compounds gave satisfactory spectral and analytical data.