Indium as a reducing agent: Selective reduction of the heterocyclic rings in quinolines, isoquinolines and quinoxalines

Synlett

Volumn , Issue 9, 1998, Pages 1029-1030

  Moody, Christopher J ^a   Pitts, Michael R ^a  

^a UNIVERSITY OF EXETER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001059891     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1836     Document Type: Article

References (13)

1. Katritzky, A. R.; Rachwal, S.; Rachwal, B. Tetrahedron 1996, 52, 15031-15070
2. For a compilation of references, see: reference 1, and Srikrishna, A.: Reddy, J. R.; Viswajanani, R. Tetrahedron 1996, 52, 1631-1636.
3. For a review, see: Cintas, P. Synlett 1995, 1087-1096.
4. For more recent uses of allylindium reagents, see: Loh, T. P.; Cao, G. Q.; Pei, J. Tetrahedron Lett. 1998, 39, 1453-1456;
5. Yi, X. H.; Meng, Y.; Li, C. J. Chem. Commun. 1998, 449-450;
6. Paquette, L. A.; Isaac, M. B. Heterocycles 1998, 47, 107-110.
7. Others have reported the use of indium hydride reagents for reduction reactions in organic synthesis: for examples, see Miyai, T.; Inone, K.; Yasuda, M.; Shibata, I.; Baba, A. Tetrahedron Lett. 1998, 39, 1929-1932;
8. Yamada, M.; Horie, T.; Kawai, M.; Yamamura, H.; Araki, S. Tetrahedron 1997, 53, 15685-15690;
9. Yamada, M.; Taneka, K.; Butsugan, Y.; Kawai, M.; Yamamura, H.; Araki, S. Main Group Metal Chem. 1997, 20, 241-246;
10. Yamada, M.; Tanaka, K.; Araki, S.; Butsugan, Y. Tetrahedron Lett. 1995, 36, 3169-3172.
11. 4) and concentrated in vacuo. The crude product was purified by flash chromatography to yield the 1,2,3,4-tetrahydro compound, the identity of which was confirmed by comparison of spectroscopic data with literature values.
12. There is a reported example of an apparent nitro group reduction in the presence of indium metal during an attempted addition of the allylindium reagent to 4-nitrobenzaldehyde (Chan, T. H.; Isaac, M. B. Pure Appl. Chem. 1996, 68, 919-924).
13. We have found that the reduction of nitro groups with indium metal is a general reaction (C. J. Moody and M. R. Pitts, Synlett 1998, 1028).