SCOPUS 정보 검색 플랫폼

Volumn 46, Issue 28, 2010, Pages 5157-5159

Domino allylic amination/Sonogashira/heterocyclisation reactions: Palladium-catalysed three-component synthesis of pyrroles

(5) Lamandé Langle, Sandrine a Abarbri, Mohamed b Thibonnet, Jérôme b Duchêne, Alain b Parrain, Jean Luc c

a NANCY UNIVERSITÉ (France)

b UNIVERSITÉ DE TOURS (France)

c AIX MARSEILLE UNIVERSITÉ (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; COPPER; PALLADIUM; PYRROLE DERIVATIVE;

AMINATION; ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; SONOGASHIRA REACTION;

EID: 77954610431 PISSN: 13597345 EISSN: None Source Type: Journal
DOI: 10.1039/c0cc00500b Document Type: Article

Times cited : (39)

References (51)

1
- 33845530046
- Pyrrole natural products with antitumor properties
- J. T. Gupton Pyrrole natural products with antitumor properties Top. Heterocycl. Chem. 2006 2 53 92
- (2006) Top. Heterocycl. Chem. , vol.2 , pp. 53-92
- Gupton, J.T.¹

2
- 38749120651
- H. Fan J. Peng M. T. Hamann J.-F. Hu Chem. Rev. 2008 108 264 287
- (2008) Chem. Rev. , vol.108 , pp. 264-287
- Fan, H.¹ Peng, J.² Hamann, M.T.³ Hu, J.-F.⁴

3
- 0003607021
- A. R. Katritzky, C. W. Rees and E. F. Scriven, Pergamon Press, Oxford, Ed.
- Comprehensive Heterocyclic Chemistry II, ed., A. R. Katritzky,,, C. W. Rees, and, E. F. Scriven,, Pergamon Press, Oxford, 1996, vol. 2, p. 207
- (1996) Comprehensive Heterocyclic Chemistry II , pp. 207

4
- 0038542691
- A. Fürstner Synlett 1999 1523
- (1999) Synlett , pp. 1523
- Fürstner, A.¹

5
- 33846334249
- S. Higgins Chem. Soc. Rev. 1997 26 247
- (1997) Chem. Soc. Rev. , vol.26 , pp. 247
- Higgins, S.¹

6
- 0003714767
- T. A. Skotheim, R. L. Elsenbaumer, and J. R. Reynolds, M. Dekker, New York, 2nd edn, Ed.
- R. D. McCullough and P. C. Ewbank, in Handbook of Conducting Polymers, ed., T. A. Skotheim,,, R. L. Elsenbaumer,, and, J. R. Reynolds,, M. Dekker, New York, 2nd edn, 1998, ch. 9
- (1998) Handbook of Conducting Polymers
- McCullough, R.D.¹ Ewbank, P.C.²

7
- 34250643020
- H. M. L. Davies S. J. Hedley Chem. Soc. Rev. 2007 36 1109 1119
- (2007) Chem. Soc. Rev. , vol.36 , pp. 1109-1119
- Davies, H.M.L.¹ Hedley, S.J.²

8
- 33644658464
- E. M. Beck N. P. Grimster R. Hatley M. J. Gaunt J. Am. Chem. Soc. 2006 128 2528 2529
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 2528-2529
- Beck, E.M.¹ Grimster, N.P.² Hatley, R.³ Gaunt, M.J.⁴

9
- 33847250872
- K. K. A. D. S. Kathriarachchi A. I. Siriwardana I. Nakamura Y. Yamamoto Tetrahedron Lett. 2007 48 2267 2270
- (2007) Tetrahedron Lett. , vol.48 , pp. 2267-2270
- Kathriarachchi, K.K.A.D.S.¹ Siriwardana, A.I.² Nakamura, I.³ Yamamoto, Y.⁴

10
- 34250666515
- H. Hamaguchi S. Kosaka H. Ohno N. Fujii T. Tanaka Chem.-Eur. J. 2007 13 1692 1708
- (2007) Chem.-Eur. J. , vol.13 , pp. 1692-1708
- Hamaguchi, H.¹ Kosaka, S.² Ohno, H.³ Fujii, N.⁴ Tanaka, T.⁵

11
- 33846268415
- M. L. Crawley I. Goljer D. J. Jenkins J. F. Mehlmann L. Nogle R. Dooley P. E. Mahaney Org. Lett. 2006 8 5837 5840
- (2006) Org. Lett. , vol.8 , pp. 5837-5840
- Crawley, M.L.¹ Goljer, I.² Jenkins, D.J.³ Mehlmann, J.F.⁴ Nogle, L.⁵ Dooley, R.⁶ Mahaney, P.E.⁷

12
- 0346456927
- P. E. R. Dhawan B. A. Arndtsen J. Am. Chem. Soc. 2004 126 468 469
- (2004) J. Am. Chem. Soc. , vol.126 , pp. 468-469
- Dhawan, P.E.R.¹ Arndtsen, B.A.²

13
- 0035969627
- R. K. Dieter H. Yu Org. Lett. 2001 3 3855 3858
- (2001) Org. Lett. , vol.3 , pp. 3855-3858
- Dieter, R.K.¹ Yu, H.²

14
- 0000078290
- For recent applications of the Paal-Knorr synthesis:
- A. Arcadi S. Di Giuseppe F. Marinelli E. Rossi Adv. Synth. Catal. 2001 343 443 446
- (2001) Adv. Synth. Catal. , vol.343 , pp. 443-446
- Arcadi, A.¹ Di Giuseppe, S.² Marinelli, F.³ Rossi, E.⁴

15
- 0033574640
- Y. Dong N. Naranjan S. L. Ablaza S.-X. Yu S. Bolvig D. A. Forsyth P. W. Le Quesne J. Org. Chem. 1999 64 2657
- (1999) J. Org. Chem. , vol.64 , pp. 2657
- Dong, Y.¹ Naranjan, N.² Ablaza, S.L.³ Yu, S.-X.⁴ Bolvig, S.⁵ Forsyth, D.A.⁶ Le Quesne, P.W.⁷

16
- 0033229862
- C. Haubmann H. Huebner P. Gmeiner Bioorg. Med. Chem. Lett. 1999 9 3143 3146
- (1999) Bioorg. Med. Chem. Lett. , vol.9 , pp. 3143-3146
- Haubmann, C.¹ Huebner, H.² Gmeiner, P.³

17
- 85047680373
- J. Robertson R. J. D. Hatley D. J. Watkin J. Chem. Soc., Perkin Trans. 1 2000 3389
- (2000) J. Chem. Soc., Perkin Trans. 1 , pp. 3389
- Robertson, J.¹ Hatley, R.J.D.² Watkin, D.J.³

18
- 0035912351
- N. R. Wurtz J. M. Turner E. E. Baird P. B. Dervan Org. Lett. 2001 3 1201 1203
- (2001) Org. Lett. , vol.3 , pp. 1201-1203
- Wurtz, N.R.¹ Turner, J.M.² Baird, E.E.³ Dervan, P.B.⁴

19
- 0034798083
- R. Ballini G. Bosica G. Fiorini G. Giarlo Synthesis 2001 2003 2006
- (2001) Synthesis , pp. 2003-2006
- Ballini, R.¹ Bosica, G.² Fiorini, G.³ Giarlo, G.⁴

20
- 0035909591
- R. U. Braun K. Zeitler T. J. J. Müller Org. Lett. 2001 3 3297 3300
- (2001) Org. Lett. , vol.3 , pp. 3297-3300
- Braun, R.U.¹ Zeitler, K.² Müller, T.J.J.³

21
- 0037027989
- J. Arrowsmith S. A. Jennings A. S. Clark M. F. G. Stevens J. Med. Chem. 2002 45 5458 5470
- (2002) J. Med. Chem. , vol.45 , pp. 5458-5470
- Arrowsmith, J.¹ Jennings, S.A.² Clark, A.S.³ Stevens, M.F.G.⁴

22
- 11144250168
- G. Balme Angew. Chem., Int. Ed. 2004 43 6238 6241
- (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 6238-6241
- Balme, G.¹

23
- 45249087881
- G. Balme D. Bouyssi N. Monteiro Heterocycles 2007 73 87 124
- (2007) Heterocycles , vol.73 , pp. 87-124
- Balme, G.¹ Bouyssi, D.² Monteiro, N.³

24
- 33847309847
- N. T. Patil Y. Yamamoto Archivoc 2007 10 121 141
- (2007) Archivoc , vol.10 , pp. 121-141
- Patil, N.T.¹ Yamamoto, Y.²

25
- 3142724941
- D. Tejedor D. Gonzalez-Cruz F. Garcia-Tellado J. J. Marrero-Tellado M. L. Rodriguez J. Am. Chem. Soc. 2004 126 8390 8391
- (2004) J. Am. Chem. Soc. , vol.126 , pp. 8390-8391
- Tejedor, D.¹ Gonzalez-Cruz, D.² Garcia-Tellado, F.³ Marrero-Tellado, J.J.⁴ Rodriguez, M.L.⁵

26
- 33745223642
- B. Alcaide P. Almendros M. C. Redondo Chem. Commun. 2006 2616 2618
- (2006) Chem. Commun. , pp. 2616-2618
- Alcaide, B.¹ Almendros, P.² Redondo, M.C.³

27
- 29044446242
- F. Lieby-Muller T. Constantieux J. Rodriguez J. Am. Chem. Soc. 2005 127 17176 17177
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 17176-17177
- Lieby-Muller, F.¹ Constantieux, T.² Rodriguez, J.³

28
- 0001613178
- S. Rousset M. Abarbri J. Thibonnet A. Duchêne J.-L. Parrain Org. Lett. 1999 1 701 703
- (1999) Org. Lett. , vol.1 , pp. 701-703
- Rousset, S.¹ Abarbri, M.² Thibonnet, J.³ Duchêne, A.⁴ Parrain, J.-L.⁵

29
- 24944538375
- K. Cherry A. Duchêne J. Thibonnet J.-L. Parrain M. Abarbri Synthesis 2005 2349 2356
- (2005) Synthesis , pp. 2349-2356
- Cherry, K.¹ Duchêne, A.² Thibonnet, J.³ Parrain, J.-L.⁴ Abarbri, M.⁵

30
- 63349099753
- S. Inack-Ngi R. Rahmani L. Commeiras G. Chouraqui J. Thibonnet A. Duchêne M. Abarbri J.-L. Parrain Adv. Synth. Catal. 2009 351 779 788
- (2009) Adv. Synth. Catal. , vol.351 , pp. 779-788
- Inack-Ngi, S.¹ Rahmani, R.² Commeiras, L.³ Chouraqui, G.⁴ Thibonnet, J.⁵ Duchêne, A.⁶ Abarbri, M.⁷ Parrain, J.-L.⁸

31
- 0034700016
- S. Rousset M. Abarbri J. Thibonnet A. Duchêne J.-L. Parrain Chem. Commun. 2000 1987 1988
- (2000) Chem. Commun. , pp. 1987-1988
- Rousset, S.¹ Abarbri, M.² Thibonnet, J.³ Duchêne, A.⁴ Parrain, J.-L.⁵

32
- 9644285669
- K. Sonogashira Y. Tohda N. Hagihara Tetrahedron Lett. 1975 16 4467 4470
- (1975) Tetrahedron Lett. , vol.16 , pp. 4467-4470
- Sonogashira, K.¹ Tohda, Y.² Hagihara, N.³

33
- 0000509322
- B. M. Trost and I. A. Fleming, Pergamon, Oxford, Ed.
- K. Sonogashira, in Comprehensive Organic Synthesis, ed., B. M. Trost, and, I. A. Fleming,, Pergamon, Oxford, 1991, vol. 3, pp. 521-549
- (1991) Comprehensive Organic Synthesis , pp. 521-549
- Sonogashira, K.¹

34
- 33947727055
- R. Chinchilla C. Najera Chem. Rev. 2007 107 874 922
- (2007) Chem. Rev. , vol.107 , pp. 874-922
- Chinchilla, R.¹ Najera, C.²

35
- 85021616948
- I. Moubarak R. Vessiere Synthesis 1980 52 54
- (1980) Synthesis , pp. 52-54
- Moubarak, I.¹ Vessiere, R.²

36
- 0026095477
- A. Padwa M. Ishida Tetrahedron Lett. 1991 32 5673 5676
- (1991) Tetrahedron Lett. , vol.32 , pp. 5673-5676
- Padwa, A.¹ Ishida, M.²

37
- 0002552491
- A. Padwa D. J. Austin M. Ishida C. L. Muller S. S. Murphree P. E. Yeske J. Org. Chem. 1992 57 1161 1169
- (1992) J. Org. Chem. , vol.57 , pp. 1161-1169
- Padwa, A.¹ Austin, D.J.² Ishida, M.³ Muller, C.L.⁴ Murphree, S.S.⁵ Yeske, P.E.⁶

38
- 84982075544
- P. Kurtz H. Gold H. Disselnkotter Justus Liebigs Ann. Chem. 1959 624 1 25
- (1959) Justus Liebigs Ann. Chem. , vol.624 , pp. 1-25
- Kurtz, P.¹ Gold, H.² Disselnkotter, H.³

39
- 77954595240
- J. Tendil J. Vemey R. Vessiere Bull. Soc. Chim. Fr. 1972 4027 4031
- (1972) Bull. Soc. Chim. Fr. , pp. 4027-4031
- Tendil, J.¹ Vemey, J.² Vessiere, R.³

40
- 2942594724
- For intermolecular palladium-catalyzed cross-coupling of amines with alkenyl bromides, see:
- X. Pan Q. Cai D. Ma Org. Lett. 2004 6 1809 1812
- (2004) Org. Lett. , vol.6 , pp. 1809-1812
- Pan, X.¹ Cai, Q.² Ma, D.³

41
- 0036408239
- J. Barluenga M. A. Fernandez F. Aznar C. Valdes Chem. Commun. 2002 2362 2363
- (2002) Chem. Commun. , pp. 2362-2363
- Barluenga, J.¹ Fernandez, M.A.² Aznar, F.³ Valdes, C.⁴

42
- 0842305925
- J. Barluenga M. A. Fernandez F. Aznar C. Valdes Chem.-Eur. J. 2004 10 494 507
- (2004) Chem.-Eur. J. , vol.10 , pp. 494-507
- Barluenga, J.¹ Fernandez, M.A.² Aznar, F.³ Valdes, C.⁴

43
- 0028027508
- Similar enynes were recently described:
- A. F. Barrero J. F. Sanchez J. E. Oltra D. Teva R. R. Ferrol J. Elmerabet R. G. Del Moral M. A. Lucena F. O'Valle Eur. J. Med. Chem. 1994 29 773 780
- (1994) Eur. J. Med. Chem. , vol.29 , pp. 773-780
- Barrero, A.F.¹ Sanchez, J.F.² Oltra, J.E.³ Teva, D.⁴ Ferrol, R.R.⁵ Elmerabet, J.⁶ Del Moral, R.G.⁷ Lucena, M.A.⁸ O'Valle, F.⁹

44
- 28044437338
- For metal catalyzed 5-endo-dig cycloisomerization of 1,5 alkynylamines, see:
- D. Steinhuebel J. M. Baxter M. Palucki I. W. Davies J. Org. Chem. 2005 70 10124 10127
- (2005) J. Org. Chem. , vol.70 , pp. 10124-10127
- Steinhuebel, D.¹ Baxter, J.M.² Palucki, M.³ Davies, I.W.⁴

45
- 0034679471
- A. L. Rodriguez C. Koradin W. Dohle P. Knochel Angew. Chem., Int. Ed. 2000 39 2488 2490
- (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 2488-2490
- Rodriguez, A.L.¹ Koradin, C.² Dohle, W.³ Knochel, P.⁴

46
- 34547106553
- Y. Yin W. Ma Z. Chai G. Zhao J. Org. Chem. 2007 72 5731 5736
- (2007) J. Org. Chem. , vol.72 , pp. 5731-5736
- Yin, Y.¹ Ma, W.² Chai, Z.³ Zhao, G.⁴

47
- 4143146341
- B. C. J. van Esseveldt F. L. van Delft J. M. M. Smits R. de Gelder H. E. Schoemaker F. P. J. T. Rutjes Adv. Synth. Catal. 2004 346 823 834
- (2004) Adv. Synth. Catal. , vol.346 , pp. 823-834
- Van Esseveldt, B.C.J.¹ Van Delft, F.L.² Smits, J.M.M.³ De Gelder, R.⁴ Schoemaker, H.E.⁵ Rutjes, F.P.J.T.⁶

48
- 33744465579
- G. A. Molander H. Hasegawa Heterocycles 2004 64 467 474
- (2004) Heterocycles , vol.64 , pp. 467-474
- Molander, G.A.¹ Hasegawa, H.²

49
- 0141852845
- B. C. J. van Esseveldt F. L. van Delft R. de Gelder F. P. J. T. Rutjes Org. Lett. 2003 5 1717 1720
- (2003) Org. Lett. , vol.5 , pp. 1717-1720
- Van Esseveldt, B.C.J.¹ Van Delft, F.L.² De Gelder, R.³ Rutjes, F.P.J.T.⁴

50
- 0037809088
- L. B. Wolf K. C. M. F. Tjen H. T. Brink R. H. Blaauw H. Hiemstra H. E. Schoemaker F. P. J. T. Rutjes Adv. Synth. Catal. 2002 344 70 83
- (2002) Adv. Synth. Catal. , vol.344 , pp. 70-83
- Wolf, L.B.¹ Tjen, K.C.M.F.² Brink, H.T.³ Blaauw, R.H.⁴ Hiemstra, H.⁵ Schoemaker, H.E.⁶ Rutjes, F.P.J.T.⁷

51
- 0347601791
- D. W. Knight C. M. Sharland Synlett 2004 119 121
- (2004) Synlett , pp. 119-121
- Knight, D.W.¹ Sharland, C.M.²

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