Reduction of quinolines to 1,2,3,4-tetrahydro derivatives employing a combination of NaCNBH3 and BF3.OEt2

Tetrahedron

Volumn 52, Issue 5, 1996, Pages 1631-1636

  Srikrishna, Adusumilli ^a   Reddy, T Jagadeeswar ^a   Viswajanani, Ranganathan ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

QUINOLINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; TECHNIQUE;

EID: 0030053407     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(95)00991-4     Document Type: Article

References (25)

1. Murahashi, S.-I.; Imada, Y.; Hirai, Y. Bull. Chem. Soc., Jpn., 1989, 62, 2968 and references cited therein.
2. Fish, R.H.; Tan, J.L.; Thormodsen, A.D. J. Org. Chem., 1984, 49, 4500. For ammonium formate mediated transfer hydrogenation see: Balczewski, P.; Joule, J.A. Synth. Commun., 1990, 20, 2815.
3. Fish, R.H.; Tan, J.L.; Thormodsen, A.D. J. Org. Chem., 1984, 49, 4500. For ammonium formate mediated transfer hydrogenation see: Balczewski, P.; Joule, J.A. Synth. Commun., 1990, 20, 2815.
4. Keller, P.C.; Marks, R.L.; Rund, J.V. Polyhedron, 1983, 2, 595. See also, Kikugawa, Y.; Saito, K.; Yamada, S.-I. Synthesis, 1978, 447.
5. Keller, P.C.; Marks, R.L.; Rund, J.V. Polyhedron, 1983, 2, 595. See also, Kikugawa, Y.; Saito, K.; Yamada, S.-I. Synthesis, 1978, 447.
6. Nose, A.; Kudo, T. Chem. Pharm. Bull., 1988, 36, 1529; 1986, 34, 3905; 1990, 38, 2097.
7. Nose, A.; Kudo, T. Chem. Pharm. Bull., 1988, 36, 1529; 1986, 34, 3905; 1990, 38, 2097.
8. Nose, A.; Kudo, T. Chem. Pharm. Bull., 1988, 36, 1529; 1986, 34, 3905; 1990, 38, 2097.
9. Gribble, G.W.; Heald, P.W. Synthesis, 1975, 650.
10. Hutchins, R.O.; Natale, N.R. Synthesis, 1979, 281.
11. Blough, B.E.; Carroll, F.I. Tetrahedron Lett., 1993, 34, 7239.
12. Srikrishna, A.; Sattigeri, J.A.; Viswajanani, R.; Yelamaggad, C.V. Synlett, 1995, 93; J. Org. Chem., 1995, 60, 2260; Srikrishna, A.; Viswajanani, Tetrahedron, 1995, 51, 3339.
13. Srikrishna, A.; Sattigeri, J.A.; Viswajanani, R.; Yelamaggad, C.V. Synlett, 1995, 93; J. Org. Chem., 1995, 60, 2260; Srikrishna, A.; Viswajanani, Tetrahedron, 1995, 51, 3339.
14. Srikrishna, A.; Sattigeri, J.A.; Viswajanani, R.; Yelamaggad, C.V. Synlett, 1995, 93; J. Org. Chem., 1995, 60, 2260; Srikrishna, A.; Viswajanani, Tetrahedron, 1995, 51, 3339.
15. Srikrishna, A.; Viswajanani, R.; Sattigeri, J.A.; Yelamaggad, C.V. Tetrahedron Lett., 1995, 36, 2347.
16. Hutchins, R.O.; Su, W.-Y; Sivakumar, R.; Cistone, F.; Stercho, Y.P. J. Org. Chem., 1983, 48, 3412.
17. Braude, E.A.; Hannah, J.; Linstead, R. J. Chem. Soc., 1960, 3249.
18. (a) Handbook of proton NMR spectra and data, Ed. Asahi Research Centre, Academic press, Vol. 7, 1986;
19. (b) Handbook of data on organic compounds, Eds. R.C. Weast and J.G. Grasselli, 2nd edition, CRC Press, Boca Raton, 1985;
20. (c) Klebe, G.; Hensen, K.; Jouanne, J.v. J. Organomet. Chem., 1983, 258, 137;
21. (d) Kokko, J.P.; Goldstein, J.H. Spectrochim. Acta, 1963, 19, 1119.
22. Srikrishna, A.; Viswajanani, R.; Sattigeri, J.A.; Vijaykumar, D. J. Org. Chem., 1995, 60, 5961.
23. Roy, R.B.; Swan, G.A. J. Chem. Soc. C, 1968, 80.
24. Willems, J.F.; van Veelen, G.F. Phot. Sci. Eng., 1962, 6, 49; Chemical Abstracts: 1962, 56, 11109f.
25. Willems, J.F.; van Veelen, G.F. Phot. Sci. Eng., 1962, 6, 49; Chemical Abstracts: 1962, 56, 11109f.