Alkali metal-mediated synthesis of 1- and 4-substituted N-alkyl-1,2,3,4-tetrahydroisoquinolines

Heterocycles

Volumn 63, Issue 2, 2004, Pages 401-409

  Azzena, Ugo ^a   Pisano, Luisa ^a   Pittalis, Mario ^a  

^a UNIVERSITY OF SASSARI   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALI METAL; LITHIUM; ORGANOMETALLIC COMPOUND; POTASSIUM; TETRAHYDROISOQUINOLINE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; ELECTRON TRANSPORT; METALLATION; NONPHOTOCHEMICAL QUENCHING; PROTON NUCLEAR MAGNETIC RESONANCE; REDUCTION; SYNTHESIS;

EID: 0842312244     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-03-9936     Document Type: Article

References (20)

1. J. Weston and H. Ahlbrecht, Tetrahedron, 1999, 55, 2289.
2. S. V. Kessar and P. Singh, Chem. Rev., 1997, 97, 721.
3. M. Schlosser and D. Limat, J. Am. Chem. Soc., 1995, 117, 12342.
4. U. Azzena, Trends in Organic Chemistry, 1997, 6, 55.
5. U. Azzena, L. Pilo, and E. Piras, Tetrahedron, 2000, 56, 3775.
6. U. Azzena, J. Chem. Soc., Perkin Trans. 1, 2002, 360.
7. R. L. Hillard III, C. A. Parnell, and K. P. C. Vollhardt, Tetrahedron, 1983, 39, 905.
8. J. W. Bunting, V. S. F. Chew, and G. Chu, J. Org. Chem., 1982, 47, 2308.
9. W. Schneider and B. Müller, Arch. Pharm. (Weinheim), 1961, 294, 360.
10. For recent reviews on the arene-catalyzed reductive metalation procedure, see: (a) M. Yus, Synlett 2001, 1197;
11. (b) D. J. Ramón and M. Yus, Eur. J. Org. Chem., 2000, 225. For a recent paper on the mechanism of this reaction, see:
12. (c) M. Yus, R. P. Herrera, and A. Guijarro, Chem. Eur. J., 2002, 8, 2574.
13. K. Hashigaki, S. Ishikawa, W. Wan, and M. Yamato, Synthesis, 1988, 1001.
14. W. Schneider and B. Müller, Arch. Pharm. (Weinheim), 1962, 295, 571.
15. H. Möhrle, E. Tot, and S. Steiner, J. Prakt. Chem., 1996, 338, 711, and references therein.
16. M. Schlosser, M. 'Organometallics in Synthesis, A Manual', ed. by M. Schlosser, Wiley, New York, 1994, pp. 1-166 (particularly pp. 18-38), and references therein.
17. W. I. O'Sullivan, F. W. Swamer, W. J. Humphlett, and C. R. Hauser, J. Org. Chem., 1961, 26, 2306.
18. J. Blagg, S. J. Coote, S. G. Davies, and B. E. Mobbs, J. Chem. Soc., Perkin Trans 1, 1986, 2257.
19. M. Freund and G. Boole, Ber., 1909, 42, 1746.
20. J. von Braun, O. Braunsdorf, and K. Räth, Ber., 1922, 55, 1666.