Cascade and sequential palladium catalysed cyclisation-azide capture-1,3-dipolar cycloaddition route to complex triazoles

Tetrahedron Letters

Volumn 39, Issue 5-6, 1998, Pages 435-438

  Gardiner, Mihaly ^a   Grigg, Ronald ^a   Sridharan, Visuvanathar ^a   Vicker, Nigel ^b  

^a UNIVERSITY OF LEEDS   (United Kingdom)

^b SANOFI   (France)

Author keywords

[No Author keywords available]

Indexed keywords

PALLADIUM; TRIAZOLE DERIVATIVE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CYCLIZATION; REACTION ANALYSIS; STEREOISOMERISM;

BETULACEAE;

EID: 0032576866     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10541-X     Document Type: Article

References (18)

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2. 1. Grigg, R.; Sansano, J. M.; Santhakumar, V.; Sridharan, V.; Thangavelanthum R.; Thornton-Pett, M.; Wilson, D., Tetrahedron, 1997, 53, 11803-11826; Grigg, R.; Brown S.; Sridharan V.; Uttley, M. D., Tetrahedron Lett., 1997, 38, 5031-5034; Grigg, R.; Pratt, R., Tetrahedron Lett., 1997, 38, 4489-4492; Grigg, R.; Loganathan, V.; Sridharan, V.; Stevenson, P.; Sukirthalingam, S.; Worakun, T., Tetrahedron, 1996, 52, 11479-11502; Grigg, R.; Savic, V., Tetrahedron Lett., 1996, 37, 6565-6568; Grigg, R.; Rasul, R.; Redpath, J.; Wilson, D.; Tetrahedron Lett., 1996, 37, 4609-4612; Grigg, R.; Sridharan, V.; Terrier, C.; Tetrahedron Lett., 1996, 37, 4221-4224; Grigg, R.; Sridharan, V.; Xu, H.-L.; J. Chem. Soc. Chem. Commun., 1995, 1903-1904; Grigg, R., J. Heterocyclic Chem., 1994, 31, 631-639.
3. 1. Grigg, R.; Sansano, J. M.; Santhakumar, V.; Sridharan, V.; Thangavelanthum R.; Thornton-Pett, M.; Wilson, D., Tetrahedron, 1997, 53, 11803-11826; Grigg, R.; Brown S.; Sridharan V.; Uttley, M. D., Tetrahedron Lett., 1997, 38, 5031-5034; Grigg, R.; Pratt, R., Tetrahedron Lett., 1997, 38, 4489-4492; Grigg, R.; Loganathan, V.; Sridharan, V.; Stevenson, P.; Sukirthalingam, S.; Worakun, T., Tetrahedron, 1996, 52, 11479-11502; Grigg, R.; Savic, V., Tetrahedron Lett., 1996, 37, 6565-6568; Grigg, R.; Rasul, R.; Redpath, J.; Wilson, D.; Tetrahedron Lett., 1996, 37, 4609-4612; Grigg, R.; Sridharan, V.; Terrier, C.; Tetrahedron Lett., 1996, 37, 4221-4224; Grigg, R.; Sridharan, V.; Xu, H.-L.; J. Chem. Soc. Chem. Commun., 1995, 1903-1904; Grigg, R., J. Heterocyclic Chem., 1994, 31, 631-639.
4. 1. Grigg, R.; Sansano, J. M.; Santhakumar, V.; Sridharan, V.; Thangavelanthum R.; Thornton-Pett, M.; Wilson, D., Tetrahedron, 1997, 53, 11803-11826; Grigg, R.; Brown S.; Sridharan V.; Uttley, M. D., Tetrahedron Lett., 1997, 38, 5031-5034; Grigg, R.; Pratt, R., Tetrahedron Lett., 1997, 38, 4489-4492; Grigg, R.; Loganathan, V.; Sridharan, V.; Stevenson, P.; Sukirthalingam, S.; Worakun, T., Tetrahedron, 1996, 52, 11479-11502; Grigg, R.; Savic, V., Tetrahedron Lett., 1996, 37, 6565-6568; Grigg, R.; Rasul, R.; Redpath, J.; Wilson, D.; Tetrahedron Lett., 1996, 37, 4609-4612; Grigg, R.; Sridharan, V.; Terrier, C.; Tetrahedron Lett., 1996, 37, 4221-4224; Grigg, R.; Sridharan, V.; Xu, H.-L.; J. Chem. Soc. Chem. Commun., 1995, 1903-1904; Grigg, R., J. Heterocyclic Chem., 1994, 31, 631-639.
5. 1. Grigg, R.; Sansano, J. M.; Santhakumar, V.; Sridharan, V.; Thangavelanthum R.; Thornton-Pett, M.; Wilson, D., Tetrahedron, 1997, 53, 11803-11826; Grigg, R.; Brown S.; Sridharan V.; Uttley, M. D., Tetrahedron Lett., 1997, 38, 5031-5034; Grigg, R.; Pratt, R., Tetrahedron Lett., 1997, 38, 4489-4492; Grigg, R.; Loganathan, V.; Sridharan, V.; Stevenson, P.; Sukirthalingam, S.; Worakun, T., Tetrahedron, 1996, 52, 11479-11502; Grigg, R.; Savic, V., Tetrahedron Lett., 1996, 37, 6565-6568; Grigg, R.; Rasul, R.; Redpath, J.; Wilson, D.; Tetrahedron Lett., 1996, 37, 4609-4612; Grigg, R.; Sridharan, V.; Terrier, C.; Tetrahedron Lett., 1996, 37, 4221-4224; Grigg, R.; Sridharan, V.; Xu, H.-L.; J. Chem. Soc. Chem. Commun., 1995, 1903-1904; Grigg, R., J. Heterocyclic Chem., 1994, 31, 631-639.
6. 1. Grigg, R.; Sansano, J. M.; Santhakumar, V.; Sridharan, V.; Thangavelanthum R.; Thornton-Pett, M.; Wilson, D., Tetrahedron, 1997, 53, 11803-11826; Grigg, R.; Brown S.; Sridharan V.; Uttley, M. D., Tetrahedron Lett., 1997, 38, 5031-5034; Grigg, R.; Pratt, R., Tetrahedron Lett., 1997, 38, 4489-4492; Grigg, R.; Loganathan, V.; Sridharan, V.; Stevenson, P.; Sukirthalingam, S.; Worakun, T., Tetrahedron, 1996, 52, 11479-11502; Grigg, R.; Savic, V., Tetrahedron Lett., 1996, 37, 6565-6568; Grigg, R.; Rasul, R.; Redpath, J.; Wilson, D.; Tetrahedron Lett., 1996, 37, 4609-4612; Grigg, R.; Sridharan, V.; Terrier, C.; Tetrahedron Lett., 1996, 37, 4221-4224; Grigg, R.; Sridharan, V.; Xu, H.-L.; J. Chem. Soc. Chem. Commun., 1995, 1903-1904; Grigg, R., J. Heterocyclic Chem., 1994, 31, 631-639.
7. 1. Grigg, R.; Sansano, J. M.; Santhakumar, V.; Sridharan, V.; Thangavelanthum R.; Thornton-Pett, M.; Wilson, D., Tetrahedron, 1997, 53, 11803-11826; Grigg, R.; Brown S.; Sridharan V.; Uttley, M. D., Tetrahedron Lett., 1997, 38, 5031-5034; Grigg, R.; Pratt, R., Tetrahedron Lett., 1997, 38, 4489-4492; Grigg, R.; Loganathan, V.; Sridharan, V.; Stevenson, P.; Sukirthalingam, S.; Worakun, T., Tetrahedron, 1996, 52, 11479-11502; Grigg, R.; Savic, V., Tetrahedron Lett., 1996, 37, 6565-6568; Grigg, R.; Rasul, R.; Redpath, J.; Wilson, D.; Tetrahedron Lett., 1996, 37, 4609-4612; Grigg, R.; Sridharan, V.; Terrier, C.; Tetrahedron Lett., 1996, 37, 4221-4224; Grigg, R.; Sridharan, V.; Xu, H.-L.; J. Chem. Soc. Chem. Commun., 1995, 1903-1904; Grigg, R., J. Heterocyclic Chem., 1994, 31, 631-639.
8. 1. Grigg, R.; Sansano, J. M.; Santhakumar, V.; Sridharan, V.; Thangavelanthum R.; Thornton-Pett, M.; Wilson, D., Tetrahedron, 1997, 53, 11803-11826; Grigg, R.; Brown S.; Sridharan V.; Uttley, M. D., Tetrahedron Lett., 1997, 38, 5031-5034; Grigg, R.; Pratt, R., Tetrahedron Lett., 1997, 38, 4489-4492; Grigg, R.; Loganathan, V.; Sridharan, V.; Stevenson, P.; Sukirthalingam, S.; Worakun, T., Tetrahedron, 1996, 52, 11479-11502; Grigg, R.; Savic, V., Tetrahedron Lett., 1996, 37, 6565-6568; Grigg, R.; Rasul, R.; Redpath, J.; Wilson, D.; Tetrahedron Lett., 1996, 37, 4609-4612; Grigg, R.; Sridharan, V.; Terrier, C.; Tetrahedron Lett., 1996, 37, 4221-4224; Grigg, R.; Sridharan, V.; Xu, H.-L.; J. Chem. Soc. Chem. Commun., 1995, 1903-1904; Grigg, R., J. Heterocyclic Chem., 1994, 31, 631-639.
9. 1. Grigg, R.; Sansano, J. M.; Santhakumar, V.; Sridharan, V.; Thangavelanthum R.; Thornton-Pett, M.; Wilson, D., Tetrahedron, 1997, 53, 11803-11826; Grigg, R.; Brown S.; Sridharan V.; Uttley, M. D., Tetrahedron Lett., 1997, 38, 5031-5034; Grigg, R.; Pratt, R., Tetrahedron Lett., 1997, 38, 4489-4492; Grigg, R.; Loganathan, V.; Sridharan, V.; Stevenson, P.; Sukirthalingam, S.; Worakun, T., Tetrahedron, 1996, 52, 11479-11502; Grigg, R.; Savic, V., Tetrahedron Lett., 1996, 37, 6565-6568; Grigg, R.; Rasul, R.; Redpath, J.; Wilson, D.; Tetrahedron Lett., 1996, 37, 4609-4612; Grigg, R.; Sridharan, V.; Terrier, C.; Tetrahedron Lett., 1996, 37, 4221-4224; Grigg, R.; Sridharan, V.; Xu, H.-L.; J. Chem. Soc. Chem. Commun., 1995, 1903-1904; Grigg, R., J. Heterocyclic Chem., 1994, 31, 631-639.
10. 2. Cyclisation: Ma, S.; Negishi, E.-I., J. Am. Chem. Soc., 1995, 117, 6345-6357; Walkup, R.D.; Gual.; Kim, Y.S.; Kim, S.W.; Tetrahedron Lett., 1995, 36, 3805-3808; Davies, I. W.; Scopes, D.I.C.; Gallagher, T., Synlett., 1993, 85-87. Cycloaddition: Larock, R.C.; Zenner, J.M., J. Org. Chem., 1995, 60, 482-483; Jeschke, T.; Wensbe, D.; Annaby, U.; Gronowitz, S.; Cohen, L.A., Tetrahedron Lett., 1993, 34, 2823-2826 and 6471-6474; Larock, R.C.; Berrios-Pena, N.G.; Fried, C.A., J. Org. Chem., 1991, 56, 2615-2617.
11. 2. Cyclisation: Ma, S.; Negishi, E.-I., J. Am. Chem. Soc., 1995, 117, 6345-6357; Walkup, R.D.; Gual.; Kim, Y.S.; Kim, S.W.; Tetrahedron Lett., 1995, 36, 3805-3808; Davies, I. W.; Scopes, D.I.C.; Gallagher, T., Synlett., 1993, 85-87. Cycloaddition: Larock, R.C.; Zenner, J.M., J. Org. Chem., 1995, 60, 482-483; Jeschke, T.; Wensbe, D.; Annaby, U.; Gronowitz, S.; Cohen, L.A., Tetrahedron Lett., 1993, 34, 2823-2826 and 6471-6474; Larock, R.C.; Berrios-Pena, N.G.; Fried, C.A., J. Org. Chem., 1991, 56, 2615-2617.
12. 2. Cyclisation: Ma, S.; Negishi, E.-I., J. Am. Chem. Soc., 1995, 117, 6345-6357; Walkup, R.D.; Gual.; Kim, Y.S.; Kim, S.W.; Tetrahedron Lett., 1995, 36, 3805-3808; Davies, I. W.; Scopes, D.I.C.; Gallagher, T., Synlett., 1993, 85-87. Cycloaddition: Larock, R.C.; Zenner, J.M., J. Org. Chem., 1995, 60, 482-483; Jeschke, T.; Wensbe, D.; Annaby, U.; Gronowitz, S.; Cohen, L.A., Tetrahedron Lett., 1993, 34, 2823-2826 and 6471-6474; Larock, R.C.; Berrios-Pena, N.G.; Fried, C.A., J. Org. Chem., 1991, 56, 2615-2617.
13. 2. Cyclisation: Ma, S.; Negishi, E.-I., J. Am. Chem. Soc., 1995, 117, 6345-6357; Walkup, R.D.; Gual.; Kim, Y.S.; Kim, S.W.; Tetrahedron Lett., 1995, 36, 3805-3808; Davies, I. W.; Scopes, D.I.C.; Gallagher, T., Synlett., 1993, 85-87. Cycloaddition: Larock, R.C.; Zenner, J.M., J. Org. Chem., 1995, 60, 482-483; Jeschke, T.; Wensbe, D.; Annaby, U.; Gronowitz, S.; Cohen, L.A., Tetrahedron Lett., 1993, 34, 2823-2826 and 6471-6474; Larock, R.C.; Berrios-Pena, N.G.; Fried, C.A., J. Org. Chem., 1991, 56, 2615-2617.
14. 2. Cyclisation: Ma, S.; Negishi, E.-I., J. Am. Chem. Soc., 1995, 117, 6345-6357; Walkup, R.D.; Gual.; Kim, Y.S.; Kim, S.W.; Tetrahedron Lett., 1995, 36, 3805-3808; Davies, I. W.; Scopes, D.I.C.; Gallagher, T., Synlett., 1993, 85-87. Cycloaddition: Larock, R.C.; Zenner, J.M., J. Org. Chem., 1995, 60, 482-483; Jeschke, T.; Wensbe, D.; Annaby, U.; Gronowitz, S.; Cohen, L.A., Tetrahedron Lett., 1993, 34, 2823-2826 and 6471-6474; Larock, R.C.; Berrios-Pena, N.G.; Fried, C.A., J. Org. Chem., 1991, 56, 2615-2617.
15. 2. Cyclisation: Ma, S.; Negishi, E.-I., J. Am. Chem. Soc., 1995, 117, 6345-6357; Walkup, R.D.; Gual.; Kim, Y.S.; Kim, S.W.; Tetrahedron Lett., 1995, 36, 3805-3808; Davies, I. W.; Scopes, D.I.C.; Gallagher, T., Synlett., 1993, 85-87. Cycloaddition: Larock, R.C.; Zenner, J.M., J. Org. Chem., 1995, 60, 482-483; Jeschke, T.; Wensbe, D.; Annaby, U.; Gronowitz, S.; Cohen, L.A., Tetrahedron Lett., 1993, 34, 2823-2826 and 6471-6474; Larock, R.C.; Berrios-Pena, N.G.; Fried, C.A., J. Org. Chem., 1991, 56, 2615-2617.
16. 3. Padwa, A. 1,3-Dipolar Cycloaddition Chemistry; John Wiley: New York, 1984; pp. 621-636.
17. 4. Yamaguchi, H.; Murata, S.; Akasaka, T.; Suzuki, T., Tetrahedron Lett., 1997, 38, 3529-3530.
18. 5. For related facile retro-Diels-Alder processes see: Grigg, R.; Xu, H.-L., Tetrahedron Lett., 1996, 37, 4251-4254.