A novel pyrrole synthesis

Organic and Biomolecular Chemistry

Volumn 2, Issue 21, 2004, Pages 3060-3062

  Agarwal, Sameer ^a   Knölker, Hans Joachim ^a  

^a DRESDEN UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ANNEALING; CONDENSATION; DRUG PRODUCTS; IONS; METALS; OXIDATION; SUBSTITUTION REACTIONS;

GRIGNARD REAGENTS; HOMOPROPARGYLAMINES; PYRROLE SYNTHESIS; SCHIFF BASES;

SILVER;

EID: 9144259637     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b412206b     Document Type: Article

References (35)

1. (a) R. J. Sundberg, Comprehensive Heterocyclic Chemistry, ed. A. R. Katritzky and C. W. Rees, Pergamon Press, Oxford, 1984, vol. 4, p. 313;
2. (b) G. P. Bean, Pyrroles, ed. R. A. Jones, Wiley, New York, 1990, p. 105;
3. (c) R. J. Sundberg, Comprehensive Heterocyclic Chemistry II, ed. A. R. Katritzky, C. W. Rees and E. F. V. Scriven, Elsevier, Oxford, 1996, vol. 2, p. 119;
4. (d) G. W. Gribble, Comprehensive Heterocyclic Chemistry II, ed. A. R. Katritzky, C. W. Rees and E. F. V. Scriven, Elsevier, Oxford, 1996, vol. 2, p. 207.
5. For selected examples, see: (a) E. J. Roskamp, P. S. Dragovich, J. B. Hartung and S. F. Pederson, J. Org. Chem., 1989, 54, 4736; (b) J. Tang and J. G. Verkade, J. Org. Chem., 1994, 59, 7793; (c) R. Grigg and V. Savic, Chem. Commun., 2000, 873; (d) V. Nair, A. U. Vinod and C. Rajesh, J. Org. Chem., 2001, 66, 4427; (e) B. C. Ranu and A. Hajra, Tetrahedron, 2001, 57, 4767; (f) B. Lagu, M. Pan and M. P. Wachter, Tetrahedron Lett., 2001, 42, 6027; (g) B. Quiclet-Sire, F. Wendeborn and S. Z. Zard, Chem. Commun., 2002, 2214; (h) P. Langer and I. Freifeld, Chem. Commun., 2002, 2668; (i) M. Yoshida, M. Kitamura and K. Narasaka, Bull. Chem. Soc. Jpn., 2003, 76, 2003; (j) D. W. Knight and C. M. Sharland, Synlett, 2003, 2258; (k) M. Yu and B. L. Pagenkopf, Org. Lett., 2003, 5, 5099; (l) R. Dhawan and B. A. Arndtsen, J. Am. Chem. Soc., 2004, 126, 468; (m) O. Flögel and H.-U. Reissig, Synlett, 2004, 895; (n) Z. Song, J. Reiner and K.. Zhao, Tetrahedron Lett., 2004, 45, 3953.
6. For selected examples, see: (a) E. J. Roskamp, P. S. Dragovich, J. B. Hartung and S. F. Pederson, J. Org. Chem., 1989, 54, 4736; (b) J. Tang and J. G. Verkade, J. Org. Chem., 1994, 59, 7793; (c) R. Grigg and V. Savic, Chem. Commun., 2000, 873; (d) V. Nair, A. U. Vinod and C. Rajesh, J. Org. Chem., 2001, 66, 4427; (e) B. C. Ranu and A. Hajra, Tetrahedron, 2001, 57, 4767; (f) B. Lagu, M. Pan and M. P. Wachter, Tetrahedron Lett., 2001, 42, 6027; (g) B. Quiclet-Sire, F. Wendeborn and S. Z. Zard, Chem. Commun., 2002, 2214; (h) P. Langer and I. Freifeld, Chem. Commun., 2002, 2668; (i) M. Yoshida, M. Kitamura and K. Narasaka, Bull. Chem. Soc. Jpn., 2003, 76, 2003; (j) D. W. Knight and C. M. Sharland, Synlett, 2003, 2258; (k) M. Yu and B. L. Pagenkopf, Org. Lett., 2003, 5, 5099; (l) R. Dhawan and B. A. Arndtsen, J. Am. Chem. Soc., 2004, 126, 468; (m) O. Flögel and H.-U. Reissig, Synlett, 2004, 895; (n) Z. Song, J. Reiner and K.. Zhao, Tetrahedron Lett., 2004, 45, 3953.
7. For selected examples, see: (a) E. J. Roskamp, P. S. Dragovich, J. B. Hartung and S. F. Pederson, J. Org. Chem., 1989, 54, 4736; (b) J. Tang and J. G. Verkade, J. Org. Chem., 1994, 59, 7793; (c) R. Grigg and V. Savic, Chem. Commun., 2000, 873; (d) V. Nair, A. U. Vinod and C. Rajesh, J. Org. Chem., 2001, 66, 4427; (e) B. C. Ranu and A. Hajra, Tetrahedron, 2001, 57, 4767; (f) B. Lagu, M. Pan and M. P. Wachter, Tetrahedron Lett., 2001, 42, 6027; (g) B. Quiclet-Sire, F. Wendeborn and S. Z. Zard, Chem. Commun., 2002, 2214; (h) P. Langer and I. Freifeld, Chem. Commun., 2002, 2668; (i) M. Yoshida, M. Kitamura and K. Narasaka, Bull. Chem. Soc. Jpn., 2003, 76, 2003; (j) D. W. Knight and C. M. Sharland, Synlett, 2003, 2258; (k) M. Yu and B. L. Pagenkopf, Org. Lett., 2003, 5, 5099; (l) R. Dhawan and B. A. Arndtsen, J. Am. Chem. Soc., 2004, 126, 468; (m) O. Flögel and H.-U. Reissig, Synlett, 2004, 895; (n) Z. Song, J. Reiner and K.. Zhao, Tetrahedron Lett., 2004, 45, 3953.
8. For selected examples, see: (a) E. J. Roskamp, P. S. Dragovich, J. B. Hartung and S. F. Pederson, J. Org. Chem., 1989, 54, 4736; (b) J. Tang and J. G. Verkade, J. Org. Chem., 1994, 59, 7793; (c) R. Grigg and V. Savic, Chem. Commun., 2000, 873; (d) V. Nair, A. U. Vinod and C. Rajesh, J. Org. Chem., 2001, 66, 4427; (e) B. C. Ranu and A. Hajra, Tetrahedron, 2001, 57, 4767; (f) B. Lagu, M. Pan and M. P. Wachter, Tetrahedron Lett., 2001, 42, 6027; (g) B. Quiclet-Sire, F. Wendeborn and S. Z. Zard, Chem. Commun., 2002, 2214; (h) P. Langer and I. Freifeld, Chem. Commun., 2002, 2668; (i) M. Yoshida, M. Kitamura and K. Narasaka, Bull. Chem. Soc. Jpn., 2003, 76, 2003; (j) D. W. Knight and C. M. Sharland, Synlett, 2003, 2258; (k) M. Yu and B. L. Pagenkopf, Org. Lett., 2003, 5, 5099; (l) R. Dhawan and B. A. Arndtsen, J. Am. Chem. Soc., 2004, 126, 468; (m) O. Flögel and H.-U. Reissig, Synlett, 2004, 895; (n) Z. Song, J. Reiner and K.. Zhao, Tetrahedron Lett., 2004, 45, 3953.
9. For selected examples, see: (a) E. J. Roskamp, P. S. Dragovich, J. B. Hartung and S. F. Pederson, J. Org. Chem., 1989, 54, 4736; (b) J. Tang and J. G. Verkade, J. Org. Chem., 1994, 59, 7793; (c) R. Grigg and V. Savic, Chem. Commun., 2000, 873; (d) V. Nair, A. U. Vinod and C. Rajesh, J. Org. Chem., 2001, 66, 4427; (e) B. C. Ranu and A. Hajra, Tetrahedron, 2001, 57, 4767; (f) B. Lagu, M. Pan and M. P. Wachter, Tetrahedron Lett., 2001, 42, 6027; (g) B. Quiclet-Sire, F. Wendeborn and S. Z. Zard, Chem. Commun., 2002, 2214; (h) P. Langer and I. Freifeld, Chem. Commun., 2002, 2668; (i) M. Yoshida, M. Kitamura and K. Narasaka, Bull. Chem. Soc. Jpn., 2003, 76, 2003; (j) D. W. Knight and C. M. Sharland, Synlett, 2003, 2258; (k) M. Yu and B. L. Pagenkopf, Org. Lett., 2003, 5, 5099; (l) R. Dhawan and B. A. Arndtsen, J. Am. Chem. Soc., 2004, 126, 468; (m) O. Flögel and H.-U. Reissig, Synlett, 2004, 895; (n) Z. Song, J. Reiner and K.. Zhao, Tetrahedron Lett., 2004, 45, 3953.
10. For selected examples, see: (a) E. J. Roskamp, P. S. Dragovich, J. B. Hartung and S. F. Pederson, J. Org. Chem., 1989, 54, 4736; (b) J. Tang and J. G. Verkade, J. Org. Chem., 1994, 59, 7793; (c) R. Grigg and V. Savic, Chem. Commun., 2000, 873; (d) V. Nair, A. U. Vinod and C. Rajesh, J. Org. Chem., 2001, 66, 4427; (e) B. C. Ranu and A. Hajra, Tetrahedron, 2001, 57, 4767; (f) B. Lagu, M. Pan and M. P. Wachter, Tetrahedron Lett., 2001, 42, 6027; (g) B. Quiclet-Sire, F. Wendeborn and S. Z. Zard, Chem. Commun., 2002, 2214; (h) P. Langer and I. Freifeld, Chem. Commun., 2002, 2668; (i) M. Yoshida, M. Kitamura and K. Narasaka, Bull. Chem. Soc. Jpn., 2003, 76, 2003; (j) D. W. Knight and C. M. Sharland, Synlett, 2003, 2258; (k) M. Yu and B. L. Pagenkopf, Org. Lett., 2003, 5, 5099; (l) R. Dhawan and B. A. Arndtsen, J. Am. Chem. Soc., 2004, 126, 468; (m) O. Flögel and H.-U. Reissig, Synlett, 2004, 895; (n) Z. Song, J. Reiner and K.. Zhao, Tetrahedron Lett., 2004, 45, 3953.
11. For selected examples, see: (a) E. J. Roskamp, P. S. Dragovich, J. B. Hartung and S. F. Pederson, J. Org. Chem., 1989, 54, 4736; (b) J. Tang and J. G. Verkade, J. Org. Chem., 1994, 59, 7793; (c) R. Grigg and V. Savic, Chem. Commun., 2000, 873; (d) V. Nair, A. U. Vinod and C. Rajesh, J. Org. Chem., 2001, 66, 4427; (e) B. C. Ranu and A. Hajra, Tetrahedron, 2001, 57, 4767; (f) B. Lagu, M. Pan and M. P. Wachter, Tetrahedron Lett., 2001, 42, 6027; (g) B. Quiclet-Sire, F. Wendeborn and S. Z. Zard, Chem. Commun., 2002, 2214; (h) P. Langer and I. Freifeld, Chem. Commun., 2002, 2668; (i) M. Yoshida, M. Kitamura and K. Narasaka, Bull. Chem. Soc. Jpn., 2003, 76, 2003; (j) D. W. Knight and C. M. Sharland, Synlett, 2003, 2258; (k) M. Yu and B. L. Pagenkopf, Org. Lett., 2003, 5, 5099; (l) R. Dhawan and B. A. Arndtsen, J. Am. Chem. Soc., 2004, 126, 468; (m) O. Flögel and H.-U. Reissig, Synlett, 2004, 895; (n) Z. Song, J. Reiner and K.. Zhao, Tetrahedron Lett., 2004, 45, 3953.
12. For selected examples, see: (a) E. J. Roskamp, P. S. Dragovich, J. B. Hartung and S. F. Pederson, J. Org. Chem., 1989, 54, 4736; (b) J. Tang and J. G. Verkade, J. Org. Chem., 1994, 59, 7793; (c) R. Grigg and V. Savic, Chem. Commun., 2000, 873; (d) V. Nair, A. U. Vinod and C. Rajesh, J. Org. Chem., 2001, 66, 4427; (e) B. C. Ranu and A. Hajra, Tetrahedron, 2001, 57, 4767; (f) B. Lagu, M. Pan and M. P. Wachter, Tetrahedron Lett., 2001, 42, 6027; (g) B. Quiclet-Sire, F. Wendeborn and S. Z. Zard, Chem. Commun., 2002, 2214; (h) P. Langer and I. Freifeld, Chem. Commun., 2002, 2668; (i) M. Yoshida, M. Kitamura and K. Narasaka, Bull. Chem. Soc. Jpn., 2003, 76, 2003; (j) D. W. Knight and C. M. Sharland, Synlett, 2003, 2258; (k) M. Yu and B. L. Pagenkopf, Org. Lett., 2003, 5, 5099; (l) R. Dhawan and B. A. Arndtsen, J. Am. Chem. Soc., 2004, 126, 468; (m) O. Flögel and H.-U. Reissig, Synlett, 2004, 895; (n) Z. Song, J. Reiner and K.. Zhao, Tetrahedron Lett., 2004, 45, 3953.
13. For selected examples, see: (a) E. J. Roskamp, P. S. Dragovich, J. B. Hartung and S. F. Pederson, J. Org. Chem., 1989, 54, 4736; (b) J. Tang and J. G. Verkade, J. Org. Chem., 1994, 59, 7793; (c) R. Grigg and V. Savic, Chem. Commun., 2000, 873; (d) V. Nair, A. U. Vinod and C. Rajesh, J. Org. Chem., 2001, 66, 4427; (e) B. C. Ranu and A. Hajra, Tetrahedron, 2001, 57, 4767; (f) B. Lagu, M. Pan and M. P. Wachter, Tetrahedron Lett., 2001, 42, 6027; (g) B. Quiclet-Sire, F. Wendeborn and S. Z. Zard, Chem. Commun., 2002, 2214; (h) P. Langer and I. Freifeld, Chem. Commun., 2002, 2668; (i) M. Yoshida, M. Kitamura and K. Narasaka, Bull. Chem. Soc. Jpn., 2003, 76, 2003; (j) D. W. Knight and C. M. Sharland, Synlett, 2003, 2258; (k) M. Yu and B. L. Pagenkopf, Org. Lett., 2003, 5, 5099; (l) R. Dhawan and B. A. Arndtsen, J. Am. Chem. Soc., 2004, 126, 468; (m) O. Flögel and H.-U. Reissig, Synlett, 2004, 895; (n) Z. Song, J. Reiner and K.. Zhao, Tetrahedron Lett., 2004, 45, 3953.
14. For selected examples, see: (a) E. J. Roskamp, P. S. Dragovich, J. B. Hartung and S. F. Pederson, J. Org. Chem., 1989, 54, 4736; (b) J. Tang and J. G. Verkade, J. Org. Chem., 1994, 59, 7793; (c) R. Grigg and V. Savic, Chem. Commun., 2000, 873; (d) V. Nair, A. U. Vinod and C. Rajesh, J. Org. Chem., 2001, 66, 4427; (e) B. C. Ranu and A. Hajra, Tetrahedron, 2001, 57, 4767; (f) B. Lagu, M. Pan and M. P. Wachter, Tetrahedron Lett., 2001, 42, 6027; (g) B. Quiclet-Sire, F. Wendeborn and S. Z. Zard, Chem. Commun., 2002, 2214; (h) P. Langer and I. Freifeld, Chem. Commun., 2002, 2668; (i) M. Yoshida, M. Kitamura and K. Narasaka, Bull. Chem. Soc. Jpn., 2003, 76, 2003; (j) D. W. Knight and C. M. Sharland, Synlett, 2003, 2258; (k) M. Yu and B. L. Pagenkopf, Org. Lett., 2003, 5, 5099; (l) R. Dhawan and B. A. Arndtsen, J. Am. Chem. Soc., 2004, 126, 468; (m) O. Flögel and H.-U. Reissig, Synlett, 2004, 895; (n) Z. Song, J. Reiner and K.. Zhao, Tetrahedron Lett., 2004, 45, 3953.
15. For selected examples, see: (a) E. J. Roskamp, P. S. Dragovich, J. B. Hartung and S. F. Pederson, J. Org. Chem., 1989, 54, 4736; (b) J. Tang and J. G. Verkade, J. Org. Chem., 1994, 59, 7793; (c) R. Grigg and V. Savic, Chem. Commun., 2000, 873; (d) V. Nair, A. U. Vinod and C. Rajesh, J. Org. Chem., 2001, 66, 4427; (e) B. C. Ranu and A. Hajra, Tetrahedron, 2001, 57, 4767; (f) B. Lagu, M. Pan and M. P. Wachter, Tetrahedron Lett., 2001, 42, 6027; (g) B. Quiclet-Sire, F. Wendeborn and S. Z. Zard, Chem. Commun., 2002, 2214; (h) P. Langer and I. Freifeld, Chem. Commun., 2002, 2668; (i) M. Yoshida, M. Kitamura and K. Narasaka, Bull. Chem. Soc. Jpn., 2003, 76, 2003; (j) D. W. Knight and C. M. Sharland, Synlett, 2003, 2258; (k) M. Yu and B. L. Pagenkopf, Org. Lett., 2003, 5, 5099; (l) R. Dhawan and B. A. Arndtsen, J. Am. Chem. Soc., 2004, 126, 468; (m) O. Flögel and H.-U. Reissig, Synlett, 2004, 895; (n) Z. Song, J. Reiner and K.. Zhao, Tetrahedron Lett., 2004, 45, 3953.
16. For selected examples, see: (a) E. J. Roskamp, P. S. Dragovich, J. B. Hartung and S. F. Pederson, J. Org. Chem., 1989, 54, 4736; (b) J. Tang and J. G. Verkade, J. Org. Chem., 1994, 59, 7793; (c) R. Grigg and V. Savic, Chem. Commun., 2000, 873; (d) V. Nair, A. U. Vinod and C. Rajesh, J. Org. Chem., 2001, 66, 4427; (e) B. C. Ranu and A. Hajra, Tetrahedron, 2001, 57, 4767; (f) B. Lagu, M. Pan and M. P. Wachter, Tetrahedron Lett., 2001, 42, 6027; (g) B. Quiclet-Sire, F. Wendeborn and S. Z. Zard, Chem. Commun., 2002, 2214; (h) P. Langer and I. Freifeld, Chem. Commun., 2002, 2668; (i) M. Yoshida, M. Kitamura and K. Narasaka, Bull. Chem. Soc. Jpn., 2003, 76, 2003; (j) D. W. Knight and C. M. Sharland, Synlett, 2003, 2258; (k) M. Yu and B. L. Pagenkopf, Org. Lett., 2003, 5, 5099; (l) R. Dhawan and B. A. Arndtsen, J. Am. Chem. Soc., 2004, 126, 468; (m) O. Flögel and H.-U. Reissig, Synlett, 2004, 895; (n) Z. Song, J. Reiner and K.. Zhao, Tetrahedron Lett., 2004, 45, 3953.
17. For selected examples, see: (a) E. J. Roskamp, P. S. Dragovich, J. B. Hartung and S. F. Pederson, J. Org. Chem., 1989, 54, 4736; (b) J. Tang and J. G. Verkade, J. Org. Chem., 1994, 59, 7793; (c) R. Grigg and V. Savic, Chem. Commun., 2000, 873; (d) V. Nair, A. U. Vinod and C. Rajesh, J. Org. Chem., 2001, 66, 4427; (e) B. C. Ranu and A. Hajra, Tetrahedron, 2001, 57, 4767; (f) B. Lagu, M. Pan and M. P. Wachter, Tetrahedron Lett., 2001, 42, 6027; (g) B. Quiclet-Sire, F. Wendeborn and S. Z. Zard, Chem. Commun., 2002, 2214; (h) P. Langer and I. Freifeld, Chem. Commun., 2002, 2668; (i) M. Yoshida, M. Kitamura and K. Narasaka, Bull. Chem. Soc. Jpn., 2003, 76, 2003; (j) D. W. Knight and C. M. Sharland, Synlett, 2003, 2258; (k) M. Yu and B. L. Pagenkopf, Org. Lett., 2003, 5, 5099; (l) R. Dhawan and B. A. Arndtsen, J. Am. Chem. Soc., 2004, 126, 468; (m) O. Flögel and H.-U. Reissig, Synlett, 2004, 895; (n) Z. Song, J. Reiner and K.. Zhao, Tetrahedron Lett., 2004, 45, 3953.
18. For selected examples, see: (a) E. J. Roskamp, P. S. Dragovich, J. B. Hartung and S. F. Pederson, J. Org. Chem., 1989, 54, 4736; (b) J. Tang and J. G. Verkade, J. Org. Chem., 1994, 59, 7793; (c) R. Grigg and V. Savic, Chem. Commun., 2000, 873; (d) V. Nair, A. U. Vinod and C. Rajesh, J. Org. Chem., 2001, 66, 4427; (e) B. C. Ranu and A. Hajra, Tetrahedron, 2001, 57, 4767; (f) B. Lagu, M. Pan and M. P. Wachter, Tetrahedron Lett., 2001, 42, 6027; (g) B. Quiclet-Sire, F. Wendeborn and S. Z. Zard, Chem. Commun., 2002, 2214; (h) P. Langer and I. Freifeld, Chem. Commun., 2002, 2668; (i) M. Yoshida, M. Kitamura and K. Narasaka, Bull. Chem. Soc. Jpn., 2003, 76, 2003; (j) D. W. Knight and C. M. Sharland, Synlett, 2003, 2258; (k) M. Yu and B. L. Pagenkopf, Org. Lett., 2003, 5, 5099; (l) R. Dhawan and B. A. Arndtsen, J. Am. Chem. Soc., 2004, 126, 468; (m) O. Flögel and H.-U. Reissig, Synlett, 2004, 895; (n) Z. Song, J. Reiner and K.. Zhao, Tetrahedron Lett., 2004, 45, 3953.
19. J. C. Pelletier and M. P. Cava, J. Org. Chem., 1987, 52, 616.
20. T. Kawate, M. Nakagawa, H. Yamazaki, M. Hirayama and T. Hino, Chem. Pharm. Bull., 1993, 41, 287.
21. J. P. Ginnebaugh, J. W. Maki and G. S. Lewandos, J. Organomet. Chem., 1980, 190, 403.
22. (a) A. Claesson, C. Sahlberg and K. Luthman, Acta Chem. Scand., 1979, 33, 309;
23. (b) J. S. Prasad and L. S. Liebeskind, Tetrahedron Lett., 1988, 29, 4253;
24. (c) M. Kimura, S. Tanaka and Y. Tamaru, Bull. Chem. Soc. Jpn., 1995, 68, 1689;
25. (d) H. Ohno, A. Toda, Y. Miwa, T. Taga, E. Osawa, Y. Yamaoka, N. Fujii and T. Ibuka, J. Org. Chem., 1999, 64, 2992;
26. (e) M. O. Amombo, A. Hausherr and H.-U. Reissig, Synlett, 1999, 1871.
27. N. Whittaker, J. Chem. Soc. C, 1969, 85.
28. (a) N. Peube-Locou, M. Plat and M. Koch, Phytochemistry, 1973, 12, 199;
29. (b) L. Angenot, C. Coune and M. Tits, J. Pharm. Belg., 1978, 33, 284;
30. (c) H.-J. Knölker and S. Cammerer, Tetrahedron Lett., 2000, 41, 5035.
31. (a) T.-S. Kam and K.-M. Sim, Phytochemistry, 1998, 47, 145;
32. (b) T. Itoh, M. Miyazaki, K. Nagata, M. Yokoya, S. Nakamura and A. Ohsawa, Heterocycles, 2002, 58, 115;
33. (c) T. Itoh, M. Miyazaki, K. Nagata, S. Nakamura and A. Ohsawa, Heterocycles, 2004, 63, 655;
34. (d) H.-J. Knölker and S. Agarwal, Synlett, 2004, 1767.
35. H.-J. Knölker, G. Baum, N. Foitzik, H. Goesmann, P. Gonser, P. G. Jones and H. Röttele, Eur. J. Inorg. Chem., 1998, 993.