The first tandem double palladium-catalyzed aminations: Synthesis of dipyrido[1,2-a:3′,2′-d]imidazole and its benzo- and aza-analogues

Chemical Communications

Volumn , Issue 21, 2004, Pages 2466-2467

  Loones, Kristof T J ^a   Maes, Bert U W ^a   Dommisse, Roger A ^a   Lemière, Guy L F ^a  

^a UNIVERSITY OF ANTWERP   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; CHLORINE DERIVATIVE; HETEROCYCLIC COMPOUND; IMIDAZOLE DERIVATIVE; PALLADIUM; PYRIDINE DERIVATIVE;

AMINATION; ARTICLE; CATALYSIS; CATALYST; MOLECULAR INTERACTION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 9444290796     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b409161b     Document Type: Article

References (26)

1. For a recent review on the Buchwald-Hartwig animation see: A. R. Muci and S. L. Buchwald, Top. Curr. Chem., 2002, 219, 131.
2. Indoles: J. A. Brown, Tetrahedron Lett., 2000, 41, 1623; M. Watanabe, T. Yamamoto and M. Nishiyama, Angew. Chem., Int. Ed. Engl., 2000, 39, 2501; K. Yamazaki, Y. Nakamura and Y. Kondo, J. Chem. Soc., Perkin Trans. 1, 2002, 2137. Indolines, 1,2,3,4-tetrahydroquinoline and 2,3,4,5-tetrahydro-1H-1-benzazepine: J. P. Wolfe, R. A. Rennels and S. L. Buchwald, Tetrahedron, 1996, 52, 7525. Pyrido[2,3-b]indoles: A. Abouabdellah and R. H. Dodd, Tetrahedron Lett., 1998, 39, 2119. Indolo[1,2-b]indazole: Y.-M. Zhu, Y. Kiyu and H. Katayama, Tetrahedron Lett., 2002, 43, 3577. Indazoles: J. J. Song and N. K. Yee, Tetrahedron Lett., 2001, 42, 2937; J. J. Song and N. K. Yee, Org. Lett., 2000, 2, 519. Phenazines: T. Emoto, N. Kubosaki, Y. Yamagiwa and T. Kamikawa, Tetrahedron Lett., 2000, 41, 355. Benzimidazoles: C. T. Brian and S. A. Brunton, Tetrahedron Lett., 2002, 43, 1893; G. Evindar and R. A. Batey, Org. Lett., 2003, 5, 133; C. T. Brian and J. T. Steer, J. Org. Chem., 2003, 68, 6814. Pyrido[1,2-a]benzimidazole: T. Iwaki, A. Yasuhara and T. Sakamoto, J. Chem. Soc., Perkin Trans, 1, 1999, 1505. Oxazepine and thiazepine: B. J. Margolis, J. J. Swidorski and B. N. Rogers, J. Org. Chem., 2003, 68, 644.
3. Indoles: J. A. Brown, Tetrahedron Let., 2000, 41, 1623; M. Watanabe, T. Yamamoto and M. Nishiyama, Angew. Chem., Int. Ed. Engl., 2000, 39, 2501; K. Yamazaki, Y. Nakamura and Y. Kondo, J. Chem. Soc., Perkin Trans. 1, 2002, 2137. Indolines, 1,2,3,4-tetrahydroquinoline and 2,3,4,5-tetrahydro-1H-1-benzazepine: J. P. Wolfe, R. A. Rennels and S. L. Buchwald, Tetrahedron, 1996, 52, 7525. Pyrido[2,3-b]indoles: A. Abouabdellah and R. H. Dodd, Tetrahedron Lett., 1998, 39, 2119. Indolo[1,2-b]indazole: Y.-M. Zhu, Y. Kiyu and H. Katayama, Tetrahedron Lett., 2002, 43, 3577. Indazoles: J. J. Song and N. K. Yee, Tetrahedron Lett., 2001, 42, 2937; J. J. Song and N. K. Yee, Org. Lett., 2000, 2, 519. Phenazines: T. Emoto, N. Kubosaki, Y. Yamagiwa and T. Kamikawa, Tetrahedron Lett., 2000, 41, 355. Benzimidazoles: C. T. Brian and S. A. Brunton, Tetrahedron Lett., 2002, 43, 1893; G. Evindar and R. A. Batey, Org. Lett., 2003, 5, 133; C. T. Brian and J. T. Steer, J. Org. Chem., 2003, 68, 6814. Pyrido[1,2-a]benzimidazole: T. Iwaki, A. Yasuhara and T. Sakamoto, J. Chem. Soc., Perkin Trans, 1, 1999, 1505. Oxazepine and thiazepine: B. J. Margolis, J. J. Swidorski and B. N. Rogers, J. Org. Chem., 2003, 68, 644.
4. Indoles: J. A. Brown, Tetrahedron Let., 2000, 41, 1623; M. Watanabe, T. Yamamoto and M. Nishiyama, Angew. Chem., Int. Ed. Engl., 2000, 39, 2501; K. Yamazaki, Y. Nakamura and Y. Kondo, J. Chem. Soc., Perkin Trans. 1, 2002, 2137. Indolines, 1,2,3,4-tetrahydroquinoline and 2,3,4,5-tetrahydro-1H-1-benzazepine: J. P. Wolfe, R. A. Rennels and S. L. Buchwald, Tetrahedron, 1996, 52, 7525. Pyrido[2,3-b]indoles: A. Abouabdellah and R. H. Dodd, Tetrahedron Lett., 1998, 39, 2119. Indolo[1,2-b]indazole: Y.-M. Zhu, Y. Kiyu and H. Katayama, Tetrahedron Lett., 2002, 43, 3577. Indazoles: J. J. Song and N. K. Yee, Tetrahedron Lett., 2001, 42, 2937; J. J. Song and N. K. Yee, Org. Lett., 2000, 2, 519. Phenazines: T. Emoto, N. Kubosaki, Y. Yamagiwa and T. Kamikawa, Tetrahedron Lett., 2000, 41, 355. Benzimidazoles: C. T. Brian and S. A. Brunton, Tetrahedron Lett., 2002, 43, 1893; G. Evindar and R. A. Batey, Org. Lett., 2003, 5, 133; C. T. Brian and J. T. Steer, J. Org. Chem., 2003, 68, 6814. Pyrido[1,2-a]benzimidazole: T. Iwaki, A. Yasuhara and T. Sakamoto, J. Chem. Soc., Perkin Trans, 1, 1999, 1505. Oxazepine and thiazepine: B. J. Margolis, J. J. Swidorski and B. N. Rogers, J. Org. Chem., 2003, 68, 644.
5. Indoles: J. A. Brown, Tetrahedron Let., 2000, 41, 1623; M. Watanabe, T. Yamamoto and M. Nishiyama, Angew. Chem., Int. Ed. Engl., 2000, 39, 2501; K. Yamazaki, Y. Nakamura and Y. Kondo, J. Chem. Soc., Perkin Trans. 1, 2002, 2137. Indolines, 1,2,3,4-tetrahydroquinoline and 2,3,4,5-tetrahydro-1H-1-benzazepine: J. P. Wolfe, R. A. Rennels and S. L. Buchwald, Tetrahedron, 1996, 52, 7525. Pyrido[2,3-b]indoles: A. Abouabdellah and R. H. Dodd, Tetrahedron Lett., 1998, 39, 2119. Indolo[1,2-b]indazole: Y.-M. Zhu, Y. Kiyu and H. Katayama, Tetrahedron Lett., 2002, 43, 3577. Indazoles: J. J. Song and N. K. Yee, Tetrahedron Lett., 2001, 42, 2937; J. J. Song and N. K. Yee, Org. Lett., 2000, 2, 519. Phenazines: T. Emoto, N. Kubosaki, Y. Yamagiwa and T. Kamikawa, Tetrahedron Lett., 2000, 41, 355. Benzimidazoles: C. T. Brian and S. A. Brunton, Tetrahedron Lett., 2002, 43, 1893; G. Evindar and R. A. Batey, Org. Lett., 2003, 5, 133; C. T. Brian and J. T. Steer, J. Org. Chem., 2003, 68, 6814. Pyrido[1,2-a]benzimidazole: T. Iwaki, A. Yasuhara and T. Sakamoto, J. Chem. Soc., Perkin Trans, 1, 1999, 1505. Oxazepine and thiazepine: B. J. Margolis, J. J. Swidorski and B. N. Rogers, J. Org. Chem., 2003, 68, 644.
6. Indoles: J. A. Brown, Tetrahedron Let., 2000, 41, 1623; M. Watanabe, T. Yamamoto and M. Nishiyama, Angew. Chem., Int. Ed. Engl., 2000, 39, 2501; K. Yamazaki, Y. Nakamura and Y. Kondo, J. Chem. Soc., Perkin Trans. 1, 2002, 2137. Indolines, 1,2,3,4-tetrahydroquinoline and 2,3,4,5-tetrahydro-1H-1-benzazepine: J. P. Wolfe, R. A. Rennels and S. L. Buchwald, Tetrahedron, 1996, 52, 7525. Pyrido[2,3-b]indoles: A. Abouabdellah and R. H. Dodd, Tetrahedron Lett., 1998, 39, 2119. Indolo[1,2-b]indazole: Y.-M. Zhu, Y. Kiyu and H. Katayama, Tetrahedron Lett., 2002, 43, 3577. Indazoles: J. J. Song and N. K. Yee, Tetrahedron Lett., 2001, 42, 2937; J. J. Song and N. K. Yee, Org. Lett., 2000, 2, 519. Phenazines: T. Emoto, N. Kubosaki, Y. Yamagiwa and T. Kamikawa, Tetrahedron Lett., 2000, 41, 355. Benzimidazoles: C. T. Brian and S. A. Brunton, Tetrahedron Lett., 2002, 43, 1893; G. Evindar and R. A. Batey, Org. Lett., 2003, 5, 133; C. T. Brian and J. T. Steer, J. Org. Chem., 2003, 68, 6814. Pyrido[1,2-a]benzimidazole: T. Iwaki, A. Yasuhara and T. Sakamoto, J. Chem. Soc., Perkin Trans, 1, 1999, 1505. Oxazepine and thiazepine: B. J. Margolis, J. J. Swidorski and B. N. Rogers, J. Org. Chem., 2003, 68, 644.
7. Indoles: J. A. Brown, Tetrahedron Let., 2000, 41, 1623; M. Watanabe, T. Yamamoto and M. Nishiyama, Angew. Chem., Int. Ed. Engl., 2000, 39, 2501; K. Yamazaki, Y. Nakamura and Y. Kondo, J. Chem. Soc., Perkin Trans. 1, 2002, 2137. Indolines, 1,2,3,4-tetrahydroquinoline and 2,3,4,5-tetrahydro-1H-1-benzazepine: J. P. Wolfe, R. A. Rennels and S. L. Buchwald, Tetrahedron, 1996, 52, 7525. Pyrido[2,3-b]indoles: A. Abouabdellah and R. H. Dodd, Tetrahedron Lett., 1998, 39, 2119. Indolo[1,2-b]indazole: Y.-M. Zhu, Y. Kiyu and H. Katayama, Tetrahedron Lett., 2002, 43, 3577. Indazoles: J. J. Song and N. K. Yee, Tetrahedron Lett., 2001, 42, 2937; J. J. Song and N. K. Yee, Org. Lett., 2000, 2, 519. Phenazines: T. Emoto, N. Kubosaki, Y. Yamagiwa and T. Kamikawa, Tetrahedron Lett., 2000, 41, 355. Benzimidazoles: C. T. Brian and S. A. Brunton, Tetrahedron Lett., 2002, 43, 1893; G. Evindar and R. A. Batey, Org. Lett., 2003, 5, 133; C. T. Brian and J. T. Steer, J. Org. Chem., 2003, 68, 6814. Pyrido[1,2-a]benzimidazole: T. Iwaki, A. Yasuhara and T. Sakamoto, J. Chem. Soc., Perkin Trans, 1, 1999, 1505. Oxazepine and thiazepine: B. J. Margolis, J. J. Swidorski and B. N. Rogers, J. Org. Chem., 2003, 68, 644.
8. Indoles: J. A. Brown, Tetrahedron Let., 2000, 41, 1623; M. Watanabe, T. Yamamoto and M. Nishiyama, Angew. Chem., Int. Ed. Engl., 2000, 39, 2501; K. Yamazaki, Y. Nakamura and Y. Kondo, J. Chem. Soc., Perkin Trans. 1, 2002, 2137. Indolines, 1,2,3,4-tetrahydroquinoline and 2,3,4,5-tetrahydro-1H-1-benzazepine: J. P. Wolfe, R. A. Rennels and S. L. Buchwald, Tetrahedron, 1996, 52, 7525. Pyrido[2,3-b]indoles: A. Abouabdellah and R. H. Dodd, Tetrahedron Lett., 1998, 39, 2119. Indolo[1,2-b]indazole: Y.-M. Zhu, Y. Kiyu and H. Katayama, Tetrahedron Lett., 2002, 43, 3577. Indazoles: J. J. Song and N. K. Yee, Tetrahedron Lett., 2001, 42, 2937; J. J. Song and N. K. Yee, Org. Lett., 2000, 2, 519. Phenazines: T. Emoto, N. Kubosaki, Y. Yamagiwa and T. Kamikawa, Tetrahedron Lett., 2000, 41, 355. Benzimidazoles: C. T. Brian and S. A. Brunton, Tetrahedron Lett., 2002, 43, 1893; G. Evindar and R. A. Batey, Org. Lett., 2003, 5, 133; C. T. Brian and J. T. Steer, J. Org. Chem., 2003, 68, 6814. Pyrido[1,2-a]benzimidazole: T. Iwaki, A. Yasuhara and T. Sakamoto, J. Chem. Soc., Perkin Trans, 1, 1999, 1505. Oxazepine and thiazepine: B. J. Margolis, J. J. Swidorski and B. N. Rogers, J. Org. Chem., 2003, 68, 644.
9. Indoles: J. A. Brown, Tetrahedron Let., 2000, 41, 1623; M. Watanabe, T. Yamamoto and M. Nishiyama, Angew. Chem., Int. Ed. Engl., 2000, 39, 2501; K. Yamazaki, Y. Nakamura and Y. Kondo, J. Chem. Soc., Perkin Trans. 1, 2002, 2137. Indolines, 1,2,3,4-tetrahydroquinoline and 2,3,4,5-tetrahydro-1H-1-benzazepine: J. P. Wolfe, R. A. Rennels and S. L. Buchwald, Tetrahedron, 1996, 52, 7525. Pyrido[2,3-b]indoles: A. Abouabdellah and R. H. Dodd, Tetrahedron Lett., 1998, 39, 2119. Indolo[1,2-b]indazole: Y.-M. Zhu, Y. Kiyu and H. Katayama, Tetrahedron Lett., 2002, 43, 3577. Indazoles: J. J. Song and N. K. Yee, Tetrahedron Lett., 2001, 42, 2937; J. J. Song and N. K. Yee, Org. Lett., 2000, 2, 519. Phenazines: T. Emoto, N. Kubosaki, Y. Yamagiwa and T. Kamikawa, Tetrahedron Lett., 2000, 41, 355. Benzimidazoles: C. T. Brian and S. A. Brunton, Tetrahedron Lett., 2002, 43, 1893; G. Evindar and R. A. Batey, Org. Lett., 2003, 5, 133; C. T. Brian and J. T. Steer, J. Org. Chem., 2003, 68, 6814. Pyrido[1,2-a]benzimidazole: T. Iwaki, A. Yasuhara and T. Sakamoto, J. Chem. Soc., Perkin Trans, 1, 1999, 1505. Oxazepine and thiazepine: B. J. Margolis, J. J. Swidorski and B. N. Rogers, J. Org. Chem., 2003, 68, 644.
10. Indoles: J. A. Brown, Tetrahedron Let., 2000, 41, 1623; M. Watanabe, T. Yamamoto and M. Nishiyama, Angew. Chem., Int. Ed. Engl., 2000, 39, 2501; K. Yamazaki, Y. Nakamura and Y. Kondo, J. Chem. Soc., Perkin Trans. 1, 2002, 2137. Indolines, 1,2,3,4-tetrahydroquinoline and 2,3,4,5-tetrahydro-1H-1-benzazepine: J. P. Wolfe, R. A. Rennels and S. L. Buchwald, Tetrahedron, 1996, 52, 7525. Pyrido[2,3-b]indoles: A. Abouabdellah and R. H. Dodd, Tetrahedron Lett., 1998, 39, 2119. Indolo[1,2-b]indazole: Y.-M. Zhu, Y. Kiyu and H. Katayama, Tetrahedron Lett., 2002, 43, 3577. Indazoles: J. J. Song and N. K. Yee, Tetrahedron Lett., 2001, 42, 2937; J. J. Song and N. K. Yee, Org. Lett., 2000, 2, 519. Phenazines: T. Emoto, N. Kubosaki, Y. Yamagiwa and T. Kamikawa, Tetrahedron Lett., 2000, 41, 355. Benzimidazoles: C. T. Brian and S. A. Brunton, Tetrahedron Lett., 2002, 43, 1893; G. Evindar and R. A. Batey, Org. Lett., 2003, 5, 133; C. T. Brian and J. T. Steer, J. Org. Chem., 2003, 68, 6814. Pyrido[1,2-a]benzimidazole: T. Iwaki, A. Yasuhara and T. Sakamoto, J. Chem. Soc., Perkin Trans, 1, 1999, 1505. Oxazepine and thiazepine: B. J. Margolis, J. J. Swidorski and B. N. Rogers, J. Org. Chem., 2003, 68, 644.
11. Indoles: J. A. Brown, Tetrahedron Let., 2000, 41, 1623; M. Watanabe, T. Yamamoto and M. Nishiyama, Angew. Chem., Int. Ed. Engl., 2000, 39, 2501; K. Yamazaki, Y. Nakamura and Y. Kondo, J. Chem. Soc., Perkin Trans. 1, 2002, 2137. Indolines, 1,2,3,4-tetrahydroquinoline and 2,3,4,5-tetrahydro-1H-1-benzazepine: J. P. Wolfe, R. A. Rennels and S. L. Buchwald, Tetrahedron, 1996, 52, 7525. Pyrido[2,3-b]indoles: A. Abouabdellah and R. H. Dodd, Tetrahedron Lett., 1998, 39, 2119. Indolo[1,2-b]indazole: Y.-M. Zhu, Y. Kiyu and H. Katayama, Tetrahedron Lett., 2002, 43, 3577. Indazoles: J. J. Song and N. K. Yee, Tetrahedron Lett., 2001, 42, 2937; J. J. Song and N. K. Yee, Org. Lett., 2000, 2, 519. Phenazines: T. Emoto, N. Kubosaki, Y. Yamagiwa and T. Kamikawa, Tetrahedron Lett., 2000, 41, 355. Benzimidazoles: C. T. Brian and S. A. Brunton, Tetrahedron Lett., 2002, 43, 1893; G. Evindar and R. A. Batey, Org. Lett., 2003, 5, 133; C. T. Brian and J. T. Steer, J. Org. Chem., 2003, 68, 6814. Pyrido[1,2-a]benzimidazole: T. Iwaki, A. Yasuhara and T. Sakamoto, J. Chem. Soc., Perkin Trans, 1, 1999, 1505. Oxazepine and thiazepine: B. J. Margolis, J. J. Swidorski and B. N. Rogers, J. Org. Chem., 2003, 68, 644.
12. Indoles: J. A. Brown, Tetrahedron Let., 2000, 41, 1623; M. Watanabe, T. Yamamoto and M. Nishiyama, Angew. Chem., Int. Ed. Engl., 2000, 39, 2501; K. Yamazaki, Y. Nakamura and Y. Kondo, J. Chem. Soc., Perkin Trans. 1, 2002, 2137. Indolines, 1,2,3,4-tetrahydroquinoline and 2,3,4,5-tetrahydro-1H-1-benzazepine: J. P. Wolfe, R. A. Rennels and S. L. Buchwald, Tetrahedron, 1996, 52, 7525. Pyrido[2,3-b]indoles: A. Abouabdellah and R. H. Dodd, Tetrahedron Lett., 1998, 39, 2119. Indolo[1,2-b]indazole: Y.-M. Zhu, Y. Kiyu and H. Katayama, Tetrahedron Lett., 2002, 43, 3577. Indazoles: J. J. Song and N. K. Yee, Tetrahedron Lett., 2001, 42, 2937; J. J. Song and N. K. Yee, Org. Lett., 2000, 2, 519. Phenazines: T. Emoto, N. Kubosaki, Y. Yamagiwa and T. Kamikawa, Tetrahedron Lett., 2000, 41, 355. Benzimidazoles: C. T. Brian and S. A. Brunton, Tetrahedron Lett., 2002, 43, 1893; G. Evindar and R. A. Batey, Org. Lett., 2003, 5, 133; C. T. Brian and J. T. Steer, J. Org. Chem., 2003, 68, 6814. Pyrido[1,2-a]benzimidazole: T. Iwaki, A. Yasuhara and T. Sakamoto, J. Chem. Soc., Perkin Trans, 1, 1999, 1505. Oxazepine and thiazepine: B. J. Margolis, J. J. Swidorski and B. N. Rogers, J. Org. Chem., 2003, 68, 644.
13. Indoles: J. A. Brown, Tetrahedron Let., 2000, 41, 1623; M. Watanabe, T. Yamamoto and M. Nishiyama, Angew. Chem., Int. Ed. Engl., 2000, 39, 2501; K. Yamazaki, Y. Nakamura and Y. Kondo, J. Chem. Soc., Perkin Trans. 1, 2002, 2137. Indolines, 1,2,3,4-tetrahydroquinoline and 2,3,4,5-tetrahydro-1H-1-benzazepine: J. P. Wolfe, R. A. Rennels and S. L. Buchwald, Tetrahedron, 1996, 52, 7525. Pyrido[2,3-b]indoles: A. Abouabdellah and R. H. Dodd, Tetrahedron Lett., 1998, 39, 2119. Indolo[1,2-b]indazole: Y.-M. Zhu, Y. Kiyu and H. Katayama, Tetrahedron Lett., 2002, 43, 3577. Indazoles: J. J. Song and N. K. Yee, Tetrahedron Lett., 2001, 42, 2937; J. J. Song and N. K. Yee, Org. Lett., 2000, 2, 519. Phenazines: T. Emoto, N. Kubosaki, Y. Yamagiwa and T. Kamikawa, Tetrahedron Lett., 2000, 41, 355. Benzimidazoles: C. T. Brian and S. A. Brunton, Tetrahedron Lett., 2002, 43, 1893; G. Evindar and R. A. Batey, Org. Lett., 2003, 5, 133; C. T. Brian and J. T. Steer, J. Org. Chem., 2003, 68, 6814. Pyrido[1,2-a]benzimidazole: T. Iwaki, A. Yasuhara and T. Sakamoto, J. Chem. Soc., Perkin Trans, 1, 1999, 1505. Oxazepine and thiazepine: B. J. Margolis, J. J. Swidorski and B. N. Rogers, J. Org. Chem., 2003, 68, 644.
14. Indoles: J. A. Brown, Tetrahedron Let., 2000, 41, 1623; M. Watanabe, T. Yamamoto and M. Nishiyama, Angew. Chem., Int. Ed. Engl., 2000, 39, 2501; K. Yamazaki, Y. Nakamura and Y. Kondo, J. Chem. Soc., Perkin Trans. 1, 2002, 2137. Indolines, 1,2,3,4-tetrahydroquinoline and 2,3,4,5-tetrahydro-1H-1-benzazepine: J. P. Wolfe, R. A. Rennels and S. L. Buchwald, Tetrahedron, 1996, 52, 7525. Pyrido[2,3-b]indoles: A. Abouabdellah and R. H. Dodd, Tetrahedron Lett., 1998, 39, 2119. Indolo[1,2-b]indazole: Y.-M. Zhu, Y. Kiyu and H. Katayama, Tetrahedron Lett., 2002, 43, 3577. Indazoles: J. J. Song and N. K. Yee, Tetrahedron Lett., 2001, 42, 2937; J. J. Song and N. K. Yee, Org. Lett., 2000, 2, 519. Phenazines: T. Emoto, N. Kubosaki, Y. Yamagiwa and T. Kamikawa, Tetrahedron Lett., 2000, 41, 355. Benzimidazoles: C. T. Brian and S. A. Brunton, Tetrahedron Lett., 2002, 43, 1893; G. Evindar and R. A. Batey, Org. Lett., 2003, 5, 133; C. T. Brian and J. T. Steer, J. Org. Chem., 2003, 68, 6814. Pyrido[1,2-a]benzimidazole: T. Iwaki, A. Yasuhara and T. Sakamoto, J. Chem. Soc., Perkin Trans, 1, 1999, 1505. Oxazepine and thiazepine: B. J. Margolis, J. J. Swidorski and B. N. Rogers, J. Org. Chem., 2003, 68, 644.
15. Indoles: J. A. Brown, Tetrahedron Let., 2000, 41, 1623; M. Watanabe, T. Yamamoto and M. Nishiyama, Angew. Chem., Int. Ed. Engl., 2000, 39, 2501; K. Yamazaki, Y. Nakamura and Y. Kondo, J. Chem. Soc., Perkin Trans. 1, 2002, 2137. Indolines, 1,2,3,4-tetrahydroquinoline and 2,3,4,5-tetrahydro-1H-1-benzazepine: J. P. Wolfe, R. A. Rennels and S. L. Buchwald, Tetrahedron, 1996, 52, 7525. Pyrido[2,3-b]indoles: A. Abouabdellah and R. H. Dodd, Tetrahedron Lett., 1998, 39, 2119. Indolo[1,2-b]indazole: Y.-M. Zhu, Y. Kiyu and H. Katayama, Tetrahedron Lett., 2002, 43, 3577. Indazoles: J. J. Song and N. K. Yee, Tetrahedron Lett., 2001, 42, 2937; J. J. Song and N. K. Yee, Org. Lett., 2000, 2, 519. Phenazines: T. Emoto, N. Kubosaki, Y. Yamagiwa and T. Kamikawa, Tetrahedron Lett., 2000, 41, 355. Benzimidazoles: C. T. Brian and S. A. Brunton, Tetrahedron Lett., 2002, 43, 1893; G. Evindar and R. A. Batey, Org. Lett., 2003, 5, 133; C. T. Brian and J. T. Steer, J. Org. Chem., 2003, 68, 6814. Pyrido[1,2-a]benzimidazole: T. Iwaki, A. Yasuhara and T. Sakamoto, J. Chem. Soc., Perkin Trans, 1, 1999, 1505. Oxazepine and thiazepine: B. J. Margolis, J. J. Swidorski and B. N. Rogers, J. Org. Chem., 2003, 68, 644.
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