A practical variation on the Paal-Knorr pyrrole synthesis

Synlett

Volumn , Issue 1, 2003, Pages 75-78

  Quiclet Sire, Béatrice ^a   Quintero, Leticia ^b   Sanchez Jimenez, Graciela ^a   Zard, Samir Z ^a  

^a LABORATOIRE DE SYNTHÈSE ORGANIQUE   (France)

^b Ctro de Invest de la F de C Q   (Mexico)

Author keywords

Furans; Paal Knorr reaction; Pyrroles; Radical additions; Xanthates

Indexed keywords

1,4 KETOALDEHYDE DERIVATIVE; ALDEHYDE DERIVATIVE; ALPHA XANTHYL KETONE; AMINE; AMMONIA; KETONE DERIVATIVE; PIVALIC ACID; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG; VINYL PIVALATE; XANTHIC ACID DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL INTERACTION; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; PAAL KNORR REACTION; SYNTHESIS;

EID: 0037240917     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (23)

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4. For some recent syntheses of pyrroles, see: (a) Kameswaran, V.; Jiang, B. Synthesis 1997, 530. (b) Knight, D. W.; Redfern, A. L.; Gilmore, J. J. Chem. Soc. Chem. Commun. 1998, 2207. (c) Shiraishi, H.; Nishitani, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1998, 63, 6234. (d) Shiraishi, H.; Nishitani, T.; Nishihana, T.; Sakaguchi, S.; Ishii, Y. Tetrahedron 1999, 55, 13957. (e) Mori, M.; Hori, K.; Akashi, M.; Hori, M.; Sato, Y.; Nishida, M. Angew. Chem. Int. Ed. 1998, 37, 636. (f) Ademitsu, U.; Tanaka, M.; Inoue, T.; Ono, N. Synthesis 1999, 471. (g) Selic, L.; Stanovnik, N. Synthesis 1999, 530. (h) Tsutsui, H.; Narasaka, K. Chem. Lett. 1999, 45. (i) Friedrich, M.; Wächtler, A.; de Meijere, A. Synlett 2002, 619. (j) Gabriele, B.; Salerno, G.; Fazio, A.; Campana, F. B. Chem. Commun. 2002, 1408. (k) Ferreira, P. M. T.; Maia, H. L. S.; Monteiro, L. S. Tetrahedron Lett. 2002, 43, 4491.
5. For some recent syntheses of pyrroles, see: (a) Kameswaran, V.; Jiang, B. Synthesis 1997, 530. (b) Knight, D. W.; Redfern, A. L.; Gilmore, J. J. Chem. Soc. Chem. Commun. 1998, 2207. (c) Shiraishi, H.; Nishitani, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1998, 63, 6234. (d) Shiraishi, H.; Nishitani, T.; Nishihana, T.; Sakaguchi, S.; Ishii, Y. Tetrahedron 1999, 55, 13957. (e) Mori, M.; Hori, K.; Akashi, M.; Hori, M.; Sato, Y.; Nishida, M. Angew. Chem. Int. Ed. 1998, 37, 636. (f) Ademitsu, U.; Tanaka, M.; Inoue, T.; Ono, N. Synthesis 1999, 471. (g) Selic, L.; Stanovnik, N. Synthesis 1999, 530. (h) Tsutsui, H.; Narasaka, K. Chem. Lett. 1999, 45. (i) Friedrich, M.; Wächtler, A.; de Meijere, A. Synlett 2002, 619. (j) Gabriele, B.; Salerno, G.; Fazio, A.; Campana, F. B. Chem. Commun. 2002, 1408. (k) Ferreira, P. M. T.; Maia, H. L. S.; Monteiro, L. S. Tetrahedron Lett. 2002, 43, 4491.
6. For some recent syntheses of pyrroles, see: (a) Kameswaran, V.; Jiang, B. Synthesis 1997, 530. (b) Knight, D. W.; Redfern, A. L.; Gilmore, J. J. Chem. Soc. Chem. Commun. 1998, 2207. (c) Shiraishi, H.; Nishitani, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1998, 63, 6234. (d) Shiraishi, H.; Nishitani, T.; Nishihana, T.; Sakaguchi, S.; Ishii, Y. Tetrahedron 1999, 55, 13957. (e) Mori, M.; Hori, K.; Akashi, M.; Hori, M.; Sato, Y.; Nishida, M. Angew. Chem. Int. Ed. 1998, 37, 636. (f) Ademitsu, U.; Tanaka, M.; Inoue, T.; Ono, N. Synthesis 1999, 471. (g) Selic, L.; Stanovnik, N. Synthesis 1999, 530. (h) Tsutsui, H.; Narasaka, K. Chem. Lett. 1999, 45. (i) Friedrich, M.; Wächtler, A.; de Meijere, A. Synlett 2002, 619. (j) Gabriele, B.; Salerno, G.; Fazio, A.; Campana, F. B. Chem. Commun. 2002, 1408. (k) Ferreira, P. M. T.; Maia, H. L. S.; Monteiro, L. S. Tetrahedron Lett. 2002, 43, 4491.
7. For some recent syntheses of pyrroles, see: (a) Kameswaran, V.; Jiang, B. Synthesis 1997, 530. (b) Knight, D. W.; Redfern, A. L.; Gilmore, J. J. Chem. Soc. Chem. Commun. 1998, 2207. (c) Shiraishi, H.; Nishitani, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1998, 63, 6234. (d) Shiraishi, H.; Nishitani, T.; Nishihana, T.; Sakaguchi, S.; Ishii, Y. Tetrahedron 1999, 55, 13957. (e) Mori, M.; Hori, K.; Akashi, M.; Hori, M.; Sato, Y.; Nishida, M. Angew. Chem. Int. Ed. 1998, 37, 636. (f) Ademitsu, U.; Tanaka, M.; Inoue, T.; Ono, N. Synthesis 1999, 471. (g) Selic, L.; Stanovnik, N. Synthesis 1999, 530. (h) Tsutsui, H.; Narasaka, K. Chem. Lett. 1999, 45. (i) Friedrich, M.; Wächtler, A.; de Meijere, A. Synlett 2002, 619. (j) Gabriele, B.; Salerno, G.; Fazio, A.; Campana, F. B. Chem. Commun. 2002, 1408. (k) Ferreira, P. M. T.; Maia, H. L. S.; Monteiro, L. S. Tetrahedron Lett. 2002, 43, 4491.
8. For some recent syntheses of pyrroles, see: (a) Kameswaran, V.; Jiang, B. Synthesis 1997, 530. (b) Knight, D. W.; Redfern, A. L.; Gilmore, J. J. Chem. Soc. Chem. Commun. 1998, 2207. (c) Shiraishi, H.; Nishitani, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1998, 63, 6234. (d) Shiraishi, H.; Nishitani, T.; Nishihana, T.; Sakaguchi, S.; Ishii, Y. Tetrahedron 1999, 55, 13957. (e) Mori, M.; Hori, K.; Akashi, M.; Hori, M.; Sato, Y.; Nishida, M. Angew. Chem. Int. Ed. 1998, 37, 636. (f) Ademitsu, U.; Tanaka, M.; Inoue, T.; Ono, N. Synthesis 1999, 471. (g) Selic, L.; Stanovnik, N. Synthesis 1999, 530. (h) Tsutsui, H.; Narasaka, K. Chem. Lett. 1999, 45. (i) Friedrich, M.; Wächtler, A.; de Meijere, A. Synlett 2002, 619. (j) Gabriele, B.; Salerno, G.; Fazio, A.; Campana, F. B. Chem. Commun. 2002, 1408. (k) Ferreira, P. M. T.; Maia, H. L. S.; Monteiro, L. S. Tetrahedron Lett. 2002, 43, 4491.
9. For some recent syntheses of pyrroles, see: (a) Kameswaran, V.; Jiang, B. Synthesis 1997, 530. (b) Knight, D. W.; Redfern, A. L.; Gilmore, J. J. Chem. Soc. Chem. Commun. 1998, 2207. (c) Shiraishi, H.; Nishitani, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1998, 63, 6234. (d) Shiraishi, H.; Nishitani, T.; Nishihana, T.; Sakaguchi, S.; Ishii, Y. Tetrahedron 1999, 55, 13957. (e) Mori, M.; Hori, K.; Akashi, M.; Hori, M.; Sato, Y.; Nishida, M. Angew. Chem. Int. Ed. 1998, 37, 636. (f) Ademitsu, U.; Tanaka, M.; Inoue, T.; Ono, N. Synthesis 1999, 471. (g) Selic, L.; Stanovnik, N. Synthesis 1999, 530. (h) Tsutsui, H.; Narasaka, K. Chem. Lett. 1999, 45. (i) Friedrich, M.; Wächtler, A.; de Meijere, A. Synlett 2002, 619. (j) Gabriele, B.; Salerno, G.; Fazio, A.; Campana, F. B. Chem. Commun. 2002, 1408. (k) Ferreira, P. M. T.; Maia, H. L. S.; Monteiro, L. S. Tetrahedron Lett. 2002, 43, 4491.
10. For some recent syntheses of pyrroles, see: (a) Kameswaran, V.; Jiang, B. Synthesis 1997, 530. (b) Knight, D. W.; Redfern, A. L.; Gilmore, J. J. Chem. Soc. Chem. Commun. 1998, 2207. (c) Shiraishi, H.; Nishitani, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1998, 63, 6234. (d) Shiraishi, H.; Nishitani, T.; Nishihana, T.; Sakaguchi, S.; Ishii, Y. Tetrahedron 1999, 55, 13957. (e) Mori, M.; Hori, K.; Akashi, M.; Hori, M.; Sato, Y.; Nishida, M. Angew. Chem. Int. Ed. 1998, 37, 636. (f) Ademitsu, U.; Tanaka, M.; Inoue, T.; Ono, N. Synthesis 1999, 471. (g) Selic, L.; Stanovnik, N. Synthesis 1999, 530. (h) Tsutsui, H.; Narasaka, K. Chem. Lett. 1999, 45. (i) Friedrich, M.; Wächtler, A.; de Meijere, A. Synlett 2002, 619. (j) Gabriele, B.; Salerno, G.; Fazio, A.; Campana, F. B. Chem. Commun. 2002, 1408. (k) Ferreira, P. M. T.; Maia, H. L. S.; Monteiro, L. S. Tetrahedron Lett. 2002, 43, 4491.
11. For some recent syntheses of pyrroles, see: (a) Kameswaran, V.; Jiang, B. Synthesis 1997, 530. (b) Knight, D. W.; Redfern, A. L.; Gilmore, J. J. Chem. Soc. Chem. Commun. 1998, 2207. (c) Shiraishi, H.; Nishitani, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1998, 63, 6234. (d) Shiraishi, H.; Nishitani, T.; Nishihana, T.; Sakaguchi, S.; Ishii, Y. Tetrahedron 1999, 55, 13957. (e) Mori, M.; Hori, K.; Akashi, M.; Hori, M.; Sato, Y.; Nishida, M. Angew. Chem. Int. Ed. 1998, 37, 636. (f) Ademitsu, U.; Tanaka, M.; Inoue, T.; Ono, N. Synthesis 1999, 471. (g) Selic, L.; Stanovnik, N. Synthesis 1999, 530. (h) Tsutsui, H.; Narasaka, K. Chem. Lett. 1999, 45. (i) Friedrich, M.; Wächtler, A.; de Meijere, A. Synlett 2002, 619. (j) Gabriele, B.; Salerno, G.; Fazio, A.; Campana, F. B. Chem. Commun. 2002, 1408. (k) Ferreira, P. M. T.; Maia, H. L. S.; Monteiro, L. S. Tetrahedron Lett. 2002, 43, 4491.
12. For some recent syntheses of pyrroles, see: (a) Kameswaran, V.; Jiang, B. Synthesis 1997, 530. (b) Knight, D. W.; Redfern, A. L.; Gilmore, J. J. Chem. Soc. Chem. Commun. 1998, 2207. (c) Shiraishi, H.; Nishitani, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1998, 63, 6234. (d) Shiraishi, H.; Nishitani, T.; Nishihana, T.; Sakaguchi, S.; Ishii, Y. Tetrahedron 1999, 55, 13957. (e) Mori, M.; Hori, K.; Akashi, M.; Hori, M.; Sato, Y.; Nishida, M. Angew. Chem. Int. Ed. 1998, 37, 636. (f) Ademitsu, U.; Tanaka, M.; Inoue, T.; Ono, N. Synthesis 1999, 471. (g) Selic, L.; Stanovnik, N. Synthesis 1999, 530. (h) Tsutsui, H.; Narasaka, K. Chem. Lett. 1999, 45. (i) Friedrich, M.; Wächtler, A.; de Meijere, A. Synlett 2002, 619. (j) Gabriele, B.; Salerno, G.; Fazio, A.; Campana, F. B. Chem. Commun. 2002, 1408. (k) Ferreira, P. M. T.; Maia, H. L. S.; Monteiro, L. S. Tetrahedron Lett. 2002, 43, 4491.
13. For some recent syntheses of pyrroles, see: (a) Kameswaran, V.; Jiang, B. Synthesis 1997, 530. (b) Knight, D. W.; Redfern, A. L.; Gilmore, J. J. Chem. Soc. Chem. Commun. 1998, 2207. (c) Shiraishi, H.; Nishitani, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1998, 63, 6234. (d) Shiraishi, H.; Nishitani, T.; Nishihana, T.; Sakaguchi, S.; Ishii, Y. Tetrahedron 1999, 55, 13957. (e) Mori, M.; Hori, K.; Akashi, M.; Hori, M.; Sato, Y.; Nishida, M. Angew. Chem. Int. Ed. 1998, 37, 636. (f) Ademitsu, U.; Tanaka, M.; Inoue, T.; Ono, N. Synthesis 1999, 471. (g) Selic, L.; Stanovnik, N. Synthesis 1999, 530. (h) Tsutsui, H.; Narasaka, K. Chem. Lett. 1999, 45. (i) Friedrich, M.; Wächtler, A.; de Meijere, A. Synlett 2002, 619. (j) Gabriele, B.; Salerno, G.; Fazio, A.; Campana, F. B. Chem. Commun. 2002, 1408. (k) Ferreira, P. M. T.; Maia, H. L. S.; Monteiro, L. S. Tetrahedron Lett. 2002, 43, 4491.
14. For some recent syntheses of pyrroles, see: (a) Kameswaran, V.; Jiang, B. Synthesis 1997, 530. (b) Knight, D. W.; Redfern, A. L.; Gilmore, J. J. Chem. Soc. Chem. Commun. 1998, 2207. (c) Shiraishi, H.; Nishitani, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1998, 63, 6234. (d) Shiraishi, H.; Nishitani, T.; Nishihana, T.; Sakaguchi, S.; Ishii, Y. Tetrahedron 1999, 55, 13957. (e) Mori, M.; Hori, K.; Akashi, M.; Hori, M.; Sato, Y.; Nishida, M. Angew. Chem. Int. Ed. 1998, 37, 636. (f) Ademitsu, U.; Tanaka, M.; Inoue, T.; Ono, N. Synthesis 1999, 471. (g) Selic, L.; Stanovnik, N. Synthesis 1999, 530. (h) Tsutsui, H.; Narasaka, K. Chem. Lett. 1999, 45. (i) Friedrich, M.; Wächtler, A.; de Meijere, A. Synlett 2002, 619. (j) Gabriele, B.; Salerno, G.; Fazio, A.; Campana, F. B. Chem. Commun. 2002, 1408. (k) Ferreira, P. M. T.; Maia, H. L. S.; Monteiro, L. S. Tetrahedron Lett. 2002, 43, 4491.
15. For some recent synthetic applications of the Paal-Knorr reaction see: (a) Trost, B. M.; Doherty, G. A. J. Am. Chem. Soc. 2000, 122, 3801. (b) Cunha, A. C.; Pereira, L. O. R.; de Souza, R. O. P.; de Souza, M. C. B. V.; Ferreira, V. F. Synth. Commun. 2000, 3215. (c) Ballini, R.; Barboni, L.; Bosica, G.; Petrini, M. Synlett 2000, 391. (d) Danks, T. N. Tetrahedron Lett. 1999, 40, 3957.
16. For some recent synthetic applications of the Paal-Knorr reaction see: (a) Trost, B. M.; Doherty, G. A. J. Am. Chem. Soc. 2000, 122, 3801. (b) Cunha, A. C.; Pereira, L. O. R.; de Souza, R. O. P.; de Souza, M. C. B. V.; Ferreira, V. F. Synth. Commun. 2000, 3215. (c) Ballini, R.; Barboni, L.; Bosica, G.; Petrini, M. Synlett 2000, 391. (d) Danks, T. N. Tetrahedron Lett. 1999, 40, 3957.
17. For some recent synthetic applications of the Paal-Knorr reaction see: (a) Trost, B. M.; Doherty, G. A. J. Am. Chem. Soc. 2000, 122, 3801. (b) Cunha, A. C.; Pereira, L. O. R.; de Souza, R. O. P.; de Souza, M. C. B. V.; Ferreira, V. F. Synth. Commun. 2000, 3215. (c) Ballini, R.; Barboni, L.; Bosica, G.; Petrini, M. Synlett 2000, 391. (d) Danks, T. N. Tetrahedron Lett. 1999, 40, 3957.
18. For some recent synthetic applications of the Paal-Knorr reaction see: (a) Trost, B. M.; Doherty, G. A. J. Am. Chem. Soc. 2000, 122, 3801. (b) Cunha, A. C.; Pereira, L. O. R.; de Souza, R. O. P.; de Souza, M. C. B. V.; Ferreira, V. F. Synth. Commun. 2000, 3215. (c) Ballini, R.; Barboni, L.; Bosica, G.; Petrini, M. Synlett 2000, 391. (d) Danks, T. N. Tetrahedron Lett. 1999, 40, 3957.
19. (a) Zard, S. Z. Angew. Chem., Int. Ed. Engl. 1997, 36, 672.
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23. 21N (%): C,87.23; H,7.69. Found (%): C,86.98; H,7.65.