Synthesis of triazolo- and tetrazolo-tetrahydroisoquinolines and isoquinolines via temperature controlled palladium catalysed allene/azide incorporation/intramolecular 1,3-dipolar cycloaddition cascades

Tetrahedron Letters

Volumn 46, Issue 35, 2005, Pages 5899-5902

  Gai, Xinjie ^a   Grigg, Ronald ^a   Rajviroongit, Shuleewan ^b   Songarsa, Saiphon ^a   Sridharan, Visuvanathar ^a  

^a UNIVERSITY OF LEEDS   (United Kingdom)

^b Mahidol University   (Thailand)

Author keywords

Catalysis; Cycloaddition; Multicomponent reaction

Indexed keywords

ALKENE; ALLENE DERIVATIVE; ALLYL COMPOUND; AZIDE; IODIDE; ISOQUINOLINE DERIVATIVE; PALLADIUM; TETRAHYDROISOQUINOLINE DERIVATIVE; TRIAZOLE DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CYCLOADDITION; STEREOCHEMISTRY;

EID: 23044505858     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.06.120     Document Type: Article

References (16)

1. K. Iwasa, M. Moriyasu, Y. Tachibana, H.S. Kim, Y. Watanya, W. Wiegrebe, K.F. Bastow, M. Cosentino, M. Kozuka, and K.H. Lee Bioorg. Med. Chem. 9 2001 2781 2884
2. H. Dhne E. Schumann Methoden der Organischen chemie (Houben Weyl) Vol. E8d 1994 Thieme Stuttgart 305
3. C. Biot, H. Baver, R.H. Schimer, and E. Davioud-Charvet J. Med. Chem. 47 2004 5972 5983
4. R.J. Herr Bioorg. Med. Chem. 10 2002 3379 3393
5. Y. Kohara, K. Kubo, E. Imamiya, Y. Inada, and T. Naka J. Med. Chem. 39 1996 5228 5235
6. A.J. Link, and D.A. Tirrell J. Am. Chem. Soc. 125 2003 11164 11165
7. A.E. Speers, G.C. Adam, and B.F. Cravatt J. Am. Chem. Soc. 125 2003 4686 4687
8. L.V. Lee, M.L. Mitchell, S.-J. Huang, V.V. Fokin, K.B. Sharpless, and C.-H. Wong J. Am. Chem. Soc. 125 2003 9588 9589
9. R. Grigg, S. Brown, V. Sridharan, and M.D. Uttley Tetrahedron Lett. 39 1998 3247 3250
10. R. Grigg, A. Liu, D. Shaw, S. Suganthan, M.L. Washington, D.E. Woodall, and G. Yoganathan Tetrahedron Lett. 41 2000 7129 7133
11. X. Gai, R. Grigg, I. Köppen, J. Marchbank, and S. Sridharan Tetrahedron Lett. 44 2003 7445 7448
12. M. Gardiner, R. Grigg, M. Kordes, V. Sridharan, and N. Vicker Tetrahedron 57 2001 7729 7735
13. M. Gardiner, R. Grigg, V. Sridharan, and N. Vicker Tetrahedron Lett. 39 1998 435 438
14. S. Kamijo, T. Jin, Z. Huo, and Y. Yamamoto J. Org. Chem. 69 2004 2386 2393
15. S. Kamijo, T. Jin, Z. Huo, and Y. Yamamoto J. Am. Chem. Soc. 125 2003 7786 7787
16. g (11.5-14.5%)..