A novel heterocumulenic Pauson-Khand reaction of alkynylcarbodiimides: A facile and efficient synthesis of heterocyclic ring-fused pyrrolinones

Heterocycles

Volumn 60, Issue 5, 2003, Pages 1045-1048

  Saito, Takao ^a   Shiotani, Masahiro ^a   Otani, Takashi ^a   Hasaba, Satoshi ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNYL GROUP; CYANAMIDE; DIMETHYL SULFOXIDE; HETEROCYCLIC COMPOUND; INDOLE DERIVATIVE; MOLYBDENUM COMPLEX; PYRROLINE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; HEATING; PAUSON KHAND REACTION; SYNTHESIS;

EID: 0038034360     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-03-9726     Document Type: Article

References (26)

1. I. U. Khand, G. R. Knox, P. L. Pauson, and W. E. Watts, J. Chem. Soc., Chem. Commun., 1971, 36; I. U. Khand, G. R. Knox, P. L. Pauson, and W. E. Watts, J. Chem. Soc., Perkin Trans. 1, 1973, 977.
2. I. U. Khand, G. R. Knox, P. L. Pauson, and W. E. Watts, J. Chem. Soc., Chem. Commun., 1971, 36; I. U. Khand, G. R. Knox, P. L. Pauson, and W. E. Watts, J. Chem. Soc., Perkin Trans. 1, 1973, 977.
3. For reviews: N. E. Score, 'Org. React.,' Vol. 40, ed. by L. A. Paquette, John Wiley & Sons, Inc., New York, 1991, p. 1; K. M. Brummond and J. L. Kent, Tetrahedron, 2000, 56, 3263; O. Geis and H.-G. Scmalz, Angew. Chem., Int. Ed. Engl., 1998, 37, 911; H.-W. Frühauf, Chem. Rev., 1997, 97, 523. For some recent reports: M. Ishizaki, M. Masamoto, and O. Hoshino, Heterocycles, 2002, 57, 1409; M. Ishizaki, H. Satoh, and O. Hoshino, Chem. Lett., 2002, 1040; T. Shibata, N. Toshida, and K. Takagi, Org. Lett., 2002, 4, 1619; M. Iqbal, N. Vyse, J. Dauvergne, and P. Evans, Tetrahedron Lett., 2002, 43, 7859; A. Becheanu and S. Laschat, Synlett, 2002, 1865.
4. For reviews: N. E. Score, 'Org. React.,' Vol. 40, ed. by L. A. Paquette, John Wiley & Sons, Inc., New York, 1991, p. 1; K. M. Brummond and J. L. Kent, Tetrahedron, 2000, 56, 3263; O. Geis and H.-G. Scmalz, Angew. Chem., Int. Ed. Engl., 1998, 37, 911; H.-W. Frühauf, Chem. Rev., 1997, 97, 523. For some recent reports: M. Ishizaki, M. Masamoto, and O. Hoshino, Heterocycles, 2002, 57, 1409; M. Ishizaki, H. Satoh, and O. Hoshino, Chem. Lett., 2002, 1040; T. Shibata, N. Toshida, and K. Takagi, Org. Lett., 2002, 4, 1619; M. Iqbal, N. Vyse, J. Dauvergne, and P. Evans, Tetrahedron Lett., 2002, 43, 7859; A. Becheanu and S. Laschat, Synlett, 2002, 1865.
5. For reviews: N. E. Score, 'Org. React.,' Vol. 40, ed. by L. A. Paquette, John Wiley & Sons, Inc., New York, 1991, p. 1; K. M. Brummond and J. L. Kent, Tetrahedron, 2000, 56, 3263; O. Geis and H.-G. Scmalz, Angew. Chem., Int. Ed. Engl., 1998, 37, 911; H.-W. Frühauf, Chem. Rev., 1997, 97, 523. For some recent reports: M. Ishizaki, M. Masamoto, and O. Hoshino, Heterocycles, 2002, 57, 1409; M. Ishizaki, H. Satoh, and O. Hoshino, Chem. Lett., 2002, 1040; T. Shibata, N. Toshida, and K. Takagi, Org. Lett., 2002, 4, 1619; M. Iqbal, N. Vyse, J. Dauvergne, and P. Evans, Tetrahedron Lett., 2002, 43, 7859; A. Becheanu and S. Laschat, Synlett, 2002, 1865.
6. For reviews: N. E. Score, 'Org. React.,' Vol. 40, ed. by L. A. Paquette, John Wiley & Sons, Inc., New York, 1991, p. 1; K. M. Brummond and J. L. Kent, Tetrahedron, 2000, 56, 3263; O. Geis and H.-G. Scmalz, Angew. Chem., Int. Ed. Engl., 1998, 37, 911; H.-W. Frühauf, Chem. Rev., 1997, 97, 523. For some recent reports: M. Ishizaki, M. Masamoto, and O. Hoshino, Heterocycles, 2002, 57, 1409; M. Ishizaki, H. Satoh, and O. Hoshino, Chem. Lett., 2002, 1040; T. Shibata, N. Toshida, and K. Takagi, Org. Lett., 2002, 4, 1619; M. Iqbal, N. Vyse, J. Dauvergne, and P. Evans, Tetrahedron Lett., 2002, 43, 7859; A. Becheanu and S. Laschat, Synlett, 2002, 1865.
7. For reviews: N. E. Score, 'Org. React.,' Vol. 40, ed. by L. A. Paquette, John Wiley & Sons, Inc., New York, 1991, p. 1; K. M. Brummond and J. L. Kent, Tetrahedron, 2000, 56, 3263; O. Geis and H.-G. Scmalz, Angew. Chem., Int. Ed. Engl., 1998, 37, 911; H.-W. Frühauf, Chem. Rev., 1997, 97, 523. For some recent reports: M. Ishizaki, M. Masamoto, and O. Hoshino, Heterocycles, 2002, 57, 1409; M. Ishizaki, H. Satoh, and O. Hoshino, Chem. Lett., 2002, 1040; T. Shibata, N. Toshida, and K. Takagi, Org. Lett., 2002, 4, 1619; M. Iqbal, N. Vyse, J. Dauvergne, and P. Evans, Tetrahedron Lett., 2002, 43, 7859; A. Becheanu and S. Laschat, Synlett, 2002, 1865.
8. For reviews: N. E. Score, 'Org. React.,' Vol. 40, ed. by L. A. Paquette, John Wiley & Sons, Inc., New York, 1991, p. 1; K. M. Brummond and J. L. Kent, Tetrahedron, 2000, 56, 3263; O. Geis and H.-G. Scmalz, Angew. Chem., Int. Ed. Engl., 1998, 37, 911; H.-W. Frühauf, Chem. Rev., 1997, 97, 523. For some recent reports: M. Ishizaki, M. Masamoto, and O. Hoshino, Heterocycles, 2002, 57, 1409; M. Ishizaki, H. Satoh, and O. Hoshino, Chem. Lett., 2002, 1040; T. Shibata, N. Toshida, and K. Takagi, Org. Lett., 2002, 4, 1619; M. Iqbal, N. Vyse, J. Dauvergne, and P. Evans, Tetrahedron Lett., 2002, 43, 7859; A. Becheanu and S. Laschat, Synlett, 2002, 1865.
9. For reviews: N. E. Score, 'Org. React.,' Vol. 40, ed. by L. A. Paquette, John Wiley & Sons, Inc., New York, 1991, p. 1; K. M. Brummond and J. L. Kent, Tetrahedron, 2000, 56, 3263; O. Geis and H.-G. Scmalz, Angew. Chem., Int. Ed. Engl., 1998, 37, 911; H.-W. Frühauf, Chem. Rev., 1997, 97, 523. For some recent reports: M. Ishizaki, M. Masamoto, and O. Hoshino, Heterocycles, 2002, 57, 1409; M. Ishizaki, H. Satoh, and O. Hoshino, Chem. Lett., 2002, 1040; T. Shibata, N. Toshida, and K. Takagi, Org. Lett., 2002, 4, 1619; M. Iqbal, N. Vyse, J. Dauvergne, and P. Evans, Tetrahedron Lett., 2002, 43, 7859; A. Becheanu and S. Laschat, Synlett, 2002, 1865.
10. For reviews: N. E. Score, 'Org. React.,' Vol. 40, ed. by L. A. Paquette, John Wiley & Sons, Inc., New York, 1991, p. 1; K. M. Brummond and J. L. Kent, Tetrahedron, 2000, 56, 3263; O. Geis and H.-G. Scmalz, Angew. Chem., Int. Ed. Engl., 1998, 37, 911; H.-W. Frühauf, Chem. Rev., 1997, 97, 523. For some recent reports: M. Ishizaki, M. Masamoto, and O. Hoshino, Heterocycles, 2002, 57, 1409; M. Ishizaki, H. Satoh, and O. Hoshino, Chem. Lett., 2002, 1040; T. Shibata, N. Toshida, and K. Takagi, Org. Lett., 2002, 4, 1619; M. Iqbal, N. Vyse, J. Dauvergne, and P. Evans, Tetrahedron Lett., 2002, 43, 7859; A. Becheanu and S. Laschat, Synlett, 2002, 1865.
11. For reviews: N. E. Score, 'Org. React.,' Vol. 40, ed. by L. A. Paquette, John Wiley & Sons, Inc., New York, 1991, p. 1; K. M. Brummond and J. L. Kent, Tetrahedron, 2000, 56, 3263; O. Geis and H.-G. Scmalz, Angew. Chem., Int. Ed. Engl., 1998, 37, 911; H.-W. Frühauf, Chem. Rev., 1997, 97, 523. For some recent reports: M. Ishizaki, M. Masamoto, and O. Hoshino, Heterocycles, 2002, 57, 1409; M. Ishizaki, H. Satoh, and O. Hoshino, Chem. Lett., 2002, 1040; T. Shibata, N. Toshida, and K. Takagi, Org. Lett., 2002, 4, 1619; M. Iqbal, N. Vyse, J. Dauvergne, and P. Evans, Tetrahedron Lett., 2002, 43, 7859; A. Becheanu and S. Laschat, Synlett, 2002, 1865.
12. J. L. Kent, H. Wan, and K. M. Brummond, Tetrahedron Lett., 1995, 36, 2407; K. M. Brummond, H. Wan, and J. L. Kent, J. Org. Chem., 1998, 63, 6535; K. M. Brummond, A. D. Kerekes, and H. Wan, J. Org. Chem., 2002, 67, 5156; M. Ahmar, F. Antras, and B. Cazes, Tetrahedron Lett., 1995, 36, 4417; M. Ahmar, O. Chabanis, J. Gauthier, and B. Cazes, Tetrahedron Lett., 1997, 38, 5277; F. Antras, M. Ahmar, and B. Cazes, Tetrahedron Lett., 2001, 42, 8157; C. Mukai, I. Nomura, K. Yamanishi, and M. Hanaoka, Org. Lett., 2002, 4, 1755.
13. J. L. Kent, H. Wan, and K. M. Brummond, Tetrahedron Lett., 1995, 36, 2407; K. M. Brummond, H. Wan, and J. L. Kent, J. Org. Chem., 1998, 63, 6535; K. M. Brummond, A. D. Kerekes, and H. Wan, J. Org. Chem., 2002, 67, 5156; M. Ahmar, F. Antras, and B. Cazes, Tetrahedron Lett., 1995, 36, 4417; M. Ahmar, O. Chabanis, J. Gauthier, and B. Cazes, Tetrahedron Lett., 1997, 38, 5277; F. Antras, M. Ahmar, and B. Cazes, Tetrahedron Lett., 2001, 42, 8157; C. Mukai, I. Nomura, K. Yamanishi, and M. Hanaoka, Org. Lett., 2002, 4, 1755.
14. J. L. Kent, H. Wan, and K. M. Brummond, Tetrahedron Lett., 1995, 36, 2407; K. M. Brummond, H. Wan, and J. L. Kent, J. Org. Chem., 1998, 63, 6535; K. M. Brummond, A. D. Kerekes, and H. Wan, J. Org. Chem., 2002, 67, 5156; M. Ahmar, F. Antras, and B. Cazes, Tetrahedron Lett., 1995, 36, 4417; M. Ahmar, O. Chabanis, J. Gauthier, and B. Cazes, Tetrahedron Lett., 1997, 38, 5277; F. Antras, M. Ahmar, and B. Cazes, Tetrahedron Lett., 2001, 42, 8157; C. Mukai, I. Nomura, K. Yamanishi, and M. Hanaoka, Org. Lett., 2002, 4, 1755.
15. J. L. Kent, H. Wan, and K. M. Brummond, Tetrahedron Lett., 1995, 36, 2407; K. M. Brummond, H. Wan, and J. L. Kent, J. Org. Chem., 1998, 63, 6535; K. M. Brummond, A. D. Kerekes, and H. Wan, J. Org. Chem., 2002, 67, 5156; M. Ahmar, F. Antras, and B. Cazes, Tetrahedron Lett., 1995, 36, 4417; M. Ahmar, O. Chabanis, J. Gauthier, and B. Cazes, Tetrahedron Lett., 1997, 38, 5277; F. Antras, M. Ahmar, and B. Cazes, Tetrahedron Lett., 2001, 42, 8157; C. Mukai, I. Nomura, K. Yamanishi, and M. Hanaoka, Org. Lett., 2002, 4, 1755.
16. J. L. Kent, H. Wan, and K. M. Brummond, Tetrahedron Lett., 1995, 36, 2407; K. M. Brummond, H. Wan, and J. L. Kent, J. Org. Chem., 1998, 63, 6535; K. M. Brummond, A. D. Kerekes, and H. Wan, J. Org. Chem., 2002, 67, 5156; M. Ahmar, F. Antras, and B. Cazes, Tetrahedron Lett., 1995, 36, 4417; M. Ahmar, O. Chabanis, J. Gauthier, and B. Cazes, Tetrahedron Lett., 1997, 38, 5277; F. Antras, M. Ahmar, and B. Cazes, Tetrahedron Lett., 2001, 42, 8157; C. Mukai, I. Nomura, K. Yamanishi, and M. Hanaoka, Org. Lett., 2002, 4, 1755.
17. J. L. Kent, H. Wan, and K. M. Brummond, Tetrahedron Lett., 1995, 36, 2407; K. M. Brummond, H. Wan, and J. L. Kent, J. Org. Chem., 1998, 63, 6535; K. M. Brummond, A. D. Kerekes, and H. Wan, J. Org. Chem., 2002, 67, 5156; M. Ahmar, F. Antras, and B. Cazes, Tetrahedron Lett., 1995, 36, 4417; M. Ahmar, O. Chabanis, J. Gauthier, and B. Cazes, Tetrahedron Lett., 1997, 38, 5277; F. Antras, M. Ahmar, and B. Cazes, Tetrahedron Lett., 2001, 42, 8157; C. Mukai, I. Nomura, K. Yamanishi, and M. Hanaoka, Org. Lett., 2002, 4, 1755.
18. J. L. Kent, H. Wan, and K. M. Brummond, Tetrahedron Lett., 1995, 36, 2407; K. M. Brummond, H. Wan, and J. L. Kent, J. Org. Chem., 1998, 63, 6535; K. M. Brummond, A. D. Kerekes, and H. Wan, J. Org. Chem., 2002, 67, 5156; M. Ahmar, F. Antras, and B. Cazes, Tetrahedron Lett., 1995, 36, 4417; M. Ahmar, O. Chabanis, J. Gauthier, and B. Cazes, Tetrahedron Lett., 1997, 38, 5277; F. Antras, M. Ahmar, and B. Cazes, Tetrahedron Lett., 2001, 42, 8157; C. Mukai, I. Nomura, K. Yamanishi, and M. Hanaoka, Org. Lett., 2002, 4, 1755.
19. 5, but which affords miscellaneous products: Y. Ohshiro, K. Kinugasa, T. Minami, and T. Agawa, J. Org. Chem., 1970, 35, 2136.
20. S. Shambayati, W. E. Crowe, and S. L. Schreiber, Tetrahedron Lett., 1990, 31, 5289; N. Jeong, Y. K. Chung, B. Y. Lee, S. H. Lee, and S.-E. Yoo, Synlett, 1991, 204.
21. S. Shambayati, W. E. Crowe, and S. L. Schreiber, Tetrahedron Lett., 1990, 31, 5289; N. Jeong, Y. K. Chung, B. Y. Lee, S. H. Lee, and S.-E. Yoo, Synlett, 1991, 204.
22. Y. K. Chung, B. Y. Lee, N. Jeong, M. Hudecek, and P. L. Pauson, Organometallics, 1993, 12, 220.
23. 2O: M 212.0950.
24. N. Jeong, S. J. Lee, B. Y. Lee, and Y. K. Chung, Tetrahedron Lett., 1993, 34, 4027; H. Cao, S. G. V. Ornum, and J. M. Cook, Tetrahedron Lett., 2000, 41, 5313.
25. N. Jeong, S. J. Lee, B. Y. Lee, and Y. K. Chung, Tetrahedron Lett., 1993, 34, 4027; H. Cao, S. G. V. Ornum, and J. M. Cook, Tetrahedron Lett., 2000, 41, 5313.
26. T. Sugihara, M. Yamada, M. Yamaguchi, and M. Nishizawa, Synlett, 1999, 771.