New chiral isoquinolinium salt derivatives from chiral primary amines via zincke reaction

Journal of Organic Chemistry

Volumn 61, Issue 26, 1996, Pages 9596-9598

  Barbier, Denis ^a   Marazano, Christian ^a   Das, Bhupesh C ^a   Potier, Pierre ^a  

^a INSTITUT DE CHIMIE DES SUBSTANCES NATURELLES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001628090     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961539b     Document Type: Article

References (13)

1. Génisson, Y.; Marazano, C.; Mehmandoust, M.; Gnecco, D.; Das, B. C. Synlett 1992, 431.
2. (a) Gnecco, D.; Marazano, C.; Das, B. C. J. Chem. Soc., Chem. Commun. 1991, 625.
3. (b) Génisson, Y.; Marazano, C.; Das, B. C. J. Org. Chem. 1993, 58, 2052.
4. (c) Wong, Y.-S.; Marazano, C.; Gnecco, D.; Das, B. C. Tetrahedron Lett. 1994, 35, 707.
5. (d) Génisson, Y.; Mehmandoust, M.; Marazano, C.; Das, B. C. Heterocycles 1994, 39, 811.
6. Zincke, T. H.; Weisspfenning, G. Justus Liebigs Ann. Chem. 1913, 396, 103. For an extension of this reaction to hydrazine derivatives, see: Agai, B.; Lempert, K. Tetrahedron 1972, 28, 2069.
7. Zincke, T. H.; Weisspfenning, G. Justus Liebigs Ann. Chem. 1913, 396, 103. For an extension of this reaction to hydrazine derivatives, see: Agai, B.; Lempert, K. Tetrahedron 1972, 28, 2069.
8. For a description of the mechanism, see ref 1 and two reviews: (a) Kost, A. N.; Gromov, S. P.; Sagitullin, R. S. Tetrahedron 1981, 37, 3423. (b) Becher, J. Synthesis 1980, 589.
9. For a description of the mechanism, see ref 1 and two reviews: (a) Kost, A. N.; Gromov, S. P.; Sagitullin, R. S. Tetrahedron 1981, 37, 3423. (b) Becher, J. Synthesis 1980, 589.
10. Polniaszek, R. P.; Kaufman, C. R. J. Am. Chem. Soc 1989, 111, 4859.
11. Zhao, B.; Snieckus, V. Tetrahedron Lett. 1991, 32, 5277.
12. For an alternative synthesis of isoquinoline 11, see: Birch, A. J.; Jackson, A. H.; Shannon, V. R. J. Chem. Soc., Perkin Trans. 1 1974, 2185.
13. Kabachnik, M. I., Zitser, A. I. Zh. Obshch. Khim. 1937, 7, 162;