Synthesis and resolution of 1,1-bi-8-methylisoquinoline: Formation of an optically active complex with high chiral recognition

Tetrahedron Asymmetry

Volumn 7, Issue 4, 1996, Pages 1027-1032

  Chelucci, Giorgio ^a   Cabras, M Antonietta ^a   Saba, Antonio ^a   Sechi, Alessandra ^a  

^a UNIVERSITY OF SASSARI   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

1,1' BIS(8 METHYLQUINOLINE); ISOQUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; COMPLEX FORMATION; DRUG PURIFICATION; ENANTIOMER; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0029974490     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00107-3     Document Type: Article

References (18)

1. Chelucci, G. Gazz. Chim. Ital. 1992, 722, 89.
2. Rosini, C.; Franzini, L; Raffaelli, A.; Salvadori, P. Synthesis, 1992, 503. Narasaka, K. Synthesis, 1991, 1. Tomioka, K. Synthesis, 1990, 541.
3. Rosini, C.; Franzini, L; Raffaelli, A.; Salvadori, P. Synthesis, 1992, 503. Narasaka, K. Synthesis, 1991, 1. Tomioka, K. Synthesis, 1990, 541.
4. Rosini, C.; Franzini, L; Raffaelli, A.; Salvadori, P. Synthesis, 1992, 503. Narasaka, K. Synthesis, 1991, 1. Tomioka, K. Synthesis, 1990, 541.
5. Tichy, M.; Závada, J.; Podlaha, J,; Vojtísek, P. Tetrahedron: Asymmetry 1995, 6, 1279.
6. Rashidi-Ranjbar, P.; Sandström, J.; Wong, H.N.C.; Wang, X.C. J. Chem, Soc., Perkin Trans. 2, 1992, 1625.
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9. Pomeranz, C. Monatsch Chem., 1897, 18, 1.
10. Tiecco, M.; Testaferri, L.; Tingoli, M.; Chianelli, D.; Montanucci, M. Synthesis, 1984, 736.
11. Wang, X.C.; Cui, Y.X.; Mak, T.C.W.; Wong, H.N.C. J. Chem Soc., Chem. Commun., 1990, 167. Roberts, N.K.; Wild, S.B. J. Am. Chem. Soc., 1979, 101, 6254, and refs therein. See also refs. 10-11.
12. Wang, X.C.; Cui, Y.X.; Mak, T.C.W.; Wong, H.N.C. J. Chem Soc., Chem. Commun., 1990, 167. Roberts, N.K.; Wild, S.B. J. Am. Chem. Soc., 1979, 101, 6254, and refs therein. See also refs. 10-11.
13. Dai, L.; Zhou, Z.; Zhang Y.; Ni, C.; Zhang, Z.; Zhou, Y. J. Chem Soc., Chem. Comm., 1987, 1760.
14. Alcock, E.W.; Hulmes, D.I.; Brown, J.M. J. Chem Soc., Chem. Comm., 1995, 395.
15. 5)-12 was obtained in 89 % yield.
16. 1/2 = 3.42 h at 20°C) and, on the basis of the measured rate constants, the biquinolyl (S)-5 should not be recovered enantiomerically pure. Moreover, the yield of the complex 12 should be greater than 50% if the newly formed R-enantiomer is intercepted. A plausible explanation can be provided by the following considerations. If the reaction of (R)-5 with (R)-10 is fast compared with the racemisation process of the S-enantiomer, the (R)-10 excess completely intercepts the newly formed R-enantiomer. The remaining (S)-5 can therefore be recovered enantiomerically pure. The yield of complex 12 (45 %) refers only to the solid collected by filtration from the reaction mixture. Since the S -enantiomer was recovered in 31% yield from the mother liquors after filtration of 12, it is possible to foresee for 12 a total yield higher than 45% (up to 69 %). For a higher yield of complex 12 (up to 89 %) see Ref. 12.
17. Roberts, N.K.; Wild, S.B. J. Chem.Soc., Dalton Trans. 1979, 2015.
18. Allen, D.G.; McLaughlin, G.M.; Robertson, G.B.; Steffen, W.L.; Salem, G.; Wild, S.B. Inorg. Chem. 1982, 21, 1007.