One-step synthesis of 3-aryl- and 3,4-diaryl-(1H)-pyrroles using tosylmethyl isocyanide (TOSMIC)

Organic Letters

Volumn 4, Issue 20, 2002, Pages 3537-3539

  Smith, Nicholas D ^a   Huang, Dehua ^a   Cosford, Nicholas D P ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYANIDE; PORPHYRIN; PYRROLE DERIVATIVE; TOSYLMETHYL ISOCYANIDE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

CYANIDES; MOLECULAR STRUCTURE; PORPHYRINS; PYRROLES;

EID: 0037015447     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0267073     Document Type: Article

References (26)

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2. Arima, K.; Imanaka, H.; Kousaka, M.; Fukuta, A.; Tamura, G. Agr. Biol. Chem. 1964, 28, 575. Nakeno, H.; Umio, S.; Kariyone, K.; Tanaka, K.; Kishimpto, T.; Noguchi, H.; Ueda, I.; Nakamura, H.; Morimoto, Y Tetrahedron Lett. 1966, 7, 737. Unverferth, K.; Engel, J.; Hofgen, N.; Rostock, A.; Gunther, R.; Lankau, H. J.; Menzer, M.; Rolfs, A.; Liebscher, J.; Muller, B.; Hofmann, H. J. J. Med. Chem. 1998, 41, 63.
3. Arima, K.; Imanaka, H.; Kousaka, M.; Fukuta, A.; Tamura, G. Agr. Biol. Chem. 1964, 28, 575. Nakeno, H.; Umio, S.; Kariyone, K.; Tanaka, K.; Kishimpto, T.; Noguchi, H.; Ueda, I.; Nakamura, H.; Morimoto, Y Tetrahedron Lett. 1966, 7, 737. Unverferth, K.; Engel, J.; Hofgen, N.; Rostock, A.; Gunther, R.; Lankau, H. J.; Menzer, M.; Rolfs, A.; Liebscher, J.; Muller, B.; Hofmann, H. J. J. Med. Chem. 1998, 41, 63.
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5. Dannhardt, G.; Kiefer, W.; Kraemer, G.; Maehrlein, S.; Nowe, U.; Fiebich, B. Eur. J. Med. Chem. 2000, 35, 499. Rango, R.; Marshall, G. R.; Santo, R. D.; Costi, R.; Massa, S.; Rompei, R.; Artico, M. Bioorg. Med. Chem. 2000, 8, 1423. Artico, M.; Santo, R. D.; Costi, R.; Massa, S.; Retico, A. J. Med. Chem. 1995, 38, 4223. Magnus, P.; Gallagher, T.; Schultz, J.; Or, Y. S.; Ananthanarayan, T. P. J. Am. Chem. Soc. 1987, 109, 2706.
6. Dannhardt, G.; Kiefer, W.; Kraemer, G.; Maehrlein, S.; Nowe, U.; Fiebich, B. Eur. J. Med. Chem. 2000, 35, 499. Rango, R.; Marshall, G. R.; Santo, R. D.; Costi, R.; Massa, S.; Rompei, R.; Artico, M. Bioorg. Med. Chem. 2000, 8, 1423. Artico, M.; Santo, R. D.; Costi, R.; Massa, S.; Retico, A. J. Med. Chem. 1995, 38, 4223. Magnus, P.; Gallagher, T.; Schultz, J.; Or, Y. S.; Ananthanarayan, T. P. J. Am. Chem. Soc. 1987, 109, 2706.
7. Dannhardt, G.; Kiefer, W.; Kraemer, G.; Maehrlein, S.; Nowe, U.; Fiebich, B. Eur. J. Med. Chem. 2000, 35, 499. Rango, R.; Marshall, G. R.; Santo, R. D.; Costi, R.; Massa, S.; Rompei, R.; Artico, M. Bioorg. Med. Chem. 2000, 8, 1423. Artico, M.; Santo, R. D.; Costi, R.; Massa, S.; Retico, A. J. Med. Chem. 1995, 38, 4223. Magnus, P.; Gallagher, T.; Schultz, J.; Or, Y. S.; Ananthanarayan, T. P. J. Am. Chem. Soc. 1987, 109, 2706.
8. Sundberg, R. G. in Comprehensive Heterocyclic Chemistry; Katritsky, A. R., Ed.; Pergamon Press: Oxford, 1984; Vol. IV, p 313. Gilchrist, T. L. In Heterocyclic Chemistry; Pitman Publishing: London, 1985; Chapters 4 and 6.
9. Sundberg, R. G. in Comprehensive Heterocyclic Chemistry; Katritsky, A. R., Ed.; Pergamon Press: Oxford, 1984; Vol. IV, p 313. Gilchrist, T. L. In Heterocyclic Chemistry; Pitman Publishing: London, 1985; Chapters 4 and 6.
10. van Leusen, A. M.; Siderius, H.; Hoogenboom, B. E.; van Lausen, D. Tetrahedron Lett. 1972, 52, 5337. Possel, O.; van Leusen, A. M. Heterocycles 1977, 7, 77. Barton, D. H. R.; Kervagoret, J.; Zard, S. Z. Tetrahedron 1990, 46, 7587. ten Have, R.; Leusink, F. R.; van Leusen, A. M. Synthesis 1996, 871. Dijkstra, H. P.; ten Have, R.; van Leusen, A. M. J. Org. Chem. 1998, 63, 5332.
11. van Leusen, A. M.; Siderius, H.; Hoogenboom, B. E.; van Lausen, D. Tetrahedron Lett. 1972, 52, 5337. Possel, O.; van Leusen, A. M. Heterocycles 1977, 7, 77. Barton, D. H. R.; Kervagoret, J.; Zard, S. Z. Tetrahedron 1990, 46, 7587. ten Have, R.; Leusink, F. R.; van Leusen, A. M. Synthesis 1996, 871. Dijkstra, H. P.; ten Have, R.; van Leusen, A. M. J. Org. Chem. 1998, 63, 5332.
12. van Leusen, A. M.; Siderius, H.; Hoogenboom, B. E.; van Lausen, D. Tetrahedron Lett. 1972, 52, 5337. Possel, O.; van Leusen, A. M. Heterocycles 1977, 7, 77. Barton, D. H. R.; Kervagoret, J.; Zard, S. Z. Tetrahedron 1990, 46, 7587. ten Have, R.; Leusink, F. R.; van Leusen, A. M. Synthesis 1996, 871. Dijkstra, H. P.; ten Have, R.; van Leusen, A. M. J. Org. Chem. 1998, 63, 5332.
13. van Leusen, A. M.; Siderius, H.; Hoogenboom, B. E.; van Lausen, D. Tetrahedron Lett. 1972, 52, 5337. Possel, O.; van Leusen, A. M. Heterocycles 1977, 7, 77. Barton, D. H. R.; Kervagoret, J.; Zard, S. Z. Tetrahedron 1990, 46, 7587. ten Have, R.; Leusink, F. R.; van Leusen, A. M. Synthesis 1996, 871. Dijkstra, H. P.; ten Have, R.; van Leusen, A. M. J. Org. Chem. 1998, 63, 5332.
14. van Leusen, A. M.; Siderius, H.; Hoogenboom, B. E.; van Lausen, D. Tetrahedron Lett. 1972, 52, 5337. Possel, O.; van Leusen, A. M. Heterocycles 1977, 7, 77. Barton, D. H. R.; Kervagoret, J.; Zard, S. Z. Tetrahedron 1990, 46, 7587. ten Have, R.; Leusink, F. R.; van Leusen, A. M. Synthesis 1996, 871. Dijkstra, H. P.; ten Have, R.; van Leusen, A. M. J. Org. Chem. 1998, 63, 5332.
15. Pavri, N. P.; Trudell, M. L. J. Org. Chem. 1997, 62, 2649.
16. Alvarez, A.; Guzman, A.; Ruiz, A.; Velarde, E. J. Org. Chem. 1992, 57, 1653. Bumagin, N. A.; Nikitina, A. F.; Belatskaya, I. P. Russ. J. Org. Chem. 1994, 30, 1619.
17. Alvarez, A.; Guzman, A.; Ruiz, A.; Velarde, E. J. Org. Chem. 1992, 57, 1653. Bumagin, N. A.; Nikitina, A. F.; Belatskaya, I. P. Russ. J. Org. Chem. 1994, 30, 1619.
18. Balasubramanian, T.; Strachan, J. P.; Boyle, P. D.; Lindsey, J. S J. Org. Chem. 2000, 65, 7919. For another example of saponification/ decarboxylation route to 3-aryl pyrroles, see: Sakai, K.; Suzuki, N.; Kenichi, N.; Yoneda, N.; Onoda, Y.; Iwasawa, Y. Chem. Pharm. Bull. 1980, 28, 2384.
19. Balasubramanian, T.; Strachan, J. P.; Boyle, P. D.; Lindsey, J. S J. Org. Chem. 2000, 65, 7919. For another example of saponification/ decarboxylation route to 3-aryl pyrroles, see: Sakai, K.; Suzuki, N.; Kenichi, N.; Yoneda, N.; Onoda, Y.; Iwasawa, Y. Chem. Pharm. Bull. 1980, 28, 2384.
20. Electron-rich arylalkenes such as 4-methoxystyrene gave low conversion upon extended reaction times at 100°C.
21. Further, 3-(phenyl)-1H-pyrrole (entry 1) was prepared previously in two steps and 32% overall yield: Boger, D. L.; Coleman, R. S.; Panek, J. S.; Yohannes, D. J. Org. Chem. 1984, 49, 4405.
22. van Leusen has reported the synthesis of 3,4-diphenyl pyrrole using a derivative of TOSMIC: van Leusen, D.; van Echten, E.; van Leusen, A. M. J. Org. Chem. 1992, 57, 2245.
23. Ono, N.; Miyagawa, H.; Ueta, T.; Ogawa, T.; Tani, H. J. Chem. Soc., Perkin Trans. 1 1998, 1595.
24. Liu, J. H.; Chan, H. W.; Wong, H. N. C. J. Org. Chem. 2000, 65, 3274.
25. Kerins, F.; O'Shea, D. F. J. Org. Chem. 2002, 67, 4968-4971 and references cited within.
26. 4, filtered, concentrated, and purified by liquid chromatography on silica gel. For full experimental details and product characterization, please see Supporting Information.