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Only the wide range of benzimidazoles can be prepared from 1,2-diaminobenzene and related compounds. For reviews on the synthesis of imidazoles, see: (a) Grimmett, M. R. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Potts, K. T., Eds.; Pergamon Press: New York, 1984; Vol. 5, pp 457-497. (b) Grimmett, M. R. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Shinkai, I., Eds.; Pergamon Press: New York, 1996; Vol. 3, pp 77-220. (c) Grimmett, M. R. In Imidazole and Benzimidazole Synthesis; Academic Press: New York, 1997. For recent imidazole syntheses,
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Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Shinkai, I., Eds.; Pergamon Press: New York
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Only the wide range of benzimidazoles can be prepared from 1,2-diaminobenzene and related compounds. For reviews on the synthesis of imidazoles, see: (a) Grimmett, M. R. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Potts, K. T., Eds.; Pergamon Press: New York, 1984; Vol. 5, pp 457-497. (b) Grimmett, M. R. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Shinkai, I., Eds.; Pergamon Press: New York, 1996; Vol. 3, pp 77-220. (c) Grimmett, M. R. In Imidazole and Benzimidazole Synthesis; Academic Press: New York, 1997. For recent imidazole syntheses,
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Grimmett, M.R.1
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10
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84943408843
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Academic Press: New York, For recent imidazole syntheses
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Only the wide range of benzimidazoles can be prepared from 1,2-diaminobenzene and related compounds. For reviews on the synthesis of imidazoles, see: (a) Grimmett, M. R. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Potts, K. T., Eds.; Pergamon Press: New York, 1984; Vol. 5, pp 457-497. (b) Grimmett, M. R. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Shinkai, I., Eds.; Pergamon Press: New York, 1996; Vol. 3, pp 77-220. (c) Grimmett, M. R. In Imidazole and Benzimidazole Synthesis; Academic Press: New York, 1997. For recent imidazole syntheses,
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Grimmett, M.R.1
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11
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0037936773
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see: (d) Sezen, B.; Sames, D. J. Am. Chem. Soc. 2003, 125, 5274. (e) Tan, K. L.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2002, 124, 13964. (f) Sisko, J.; Kassick, A. J.; Mellinger, M.; Filan, J. J.; Allen, A.; Olsen, M. A. J. Org. Chem. 2000, 65, 1516. (g) Sisko, J. J. Org. Chem. 1998, 63, 4529. (h) Groarke, M.; McKervey, M. A.; Nieuwenhuyzen, M. Tetrahedron Lett. 2000, 41, 1275. (i) Rolfs, A.; Liebscher, J. J. Org. Chem. 1997, 62, 3480. (j) Matsumura, K.; Kuritani, M.; Shimadzu, H.; Hashimoto, N. Chem. Pharm. Bull. 1976, 24, 960. (k) Roesler, P. P.; Kille, G.; Fleury, J.-P. Bull. Soc. Chim. Fr. 1967, 545.
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Sames, D.2
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see: (d) Sezen, B.; Sames, D. J. Am. Chem. Soc. 2003, 125, 5274. (e) Tan, K. L.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2002, 124, 13964. (f) Sisko, J.; Kassick, A. J.; Mellinger, M.; Filan, J. J.; Allen, A.; Olsen, M. A. J. Org. Chem. 2000, 65, 1516. (g) Sisko, J. J. Org. Chem. 1998, 63, 4529. (h) Groarke, M.; McKervey, M. A.; Nieuwenhuyzen, M. Tetrahedron Lett. 2000, 41, 1275. (i) Rolfs, A.; Liebscher, J. J. Org. Chem. 1997, 62, 3480. (j) Matsumura, K.; Kuritani, M.; Shimadzu, H.; Hashimoto, N. Chem. Pharm. Bull. 1976, 24, 960. (k) Roesler, P. P.; Kille, G.; Fleury, J.-P. Bull. Soc. Chim. Fr. 1967, 545.
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Tan, K.L.1
Bergman, R.G.2
Ellman, J.A.3
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13
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see: (d) Sezen, B.; Sames, D. J. Am. Chem. Soc. 2003, 125, 5274. (e) Tan, K. L.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2002, 124, 13964. (f) Sisko, J.; Kassick, A. J.; Mellinger, M.; Filan, J. J.; Allen, A.; Olsen, M. A. J. Org. Chem. 2000, 65, 1516. (g) Sisko, J. J. Org. Chem. 1998, 63, 4529. (h) Groarke, M.; McKervey, M. A.; Nieuwenhuyzen, M. Tetrahedron Lett. 2000, 41, 1275. (i) Rolfs, A.; Liebscher, J. J. Org. Chem. 1997, 62, 3480. (j) Matsumura, K.; Kuritani, M.; Shimadzu, H.; Hashimoto, N. Chem. Pharm. Bull. 1976, 24, 960. (k) Roesler, P. P.; Kille, G.; Fleury, J.-P. Bull. Soc. Chim. Fr. 1967, 545.
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Sisko, J.1
Kassick, A.J.2
Mellinger, M.3
Filan, J.J.4
Allen, A.5
Olsen, M.A.6
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14
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0032568905
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see: (d) Sezen, B.; Sames, D. J. Am. Chem. Soc. 2003, 125, 5274. (e) Tan, K. L.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2002, 124, 13964. (f) Sisko, J.; Kassick, A. J.; Mellinger, M.; Filan, J. J.; Allen, A.; Olsen, M. A. J. Org. Chem. 2000, 65, 1516. (g) Sisko, J. J. Org. Chem. 1998, 63, 4529. (h) Groarke, M.; McKervey, M. A.; Nieuwenhuyzen, M. Tetrahedron Lett. 2000, 41, 1275. (i) Rolfs, A.; Liebscher, J. J. Org. Chem. 1997, 62, 3480. (j) Matsumura, K.; Kuritani, M.; Shimadzu, H.; Hashimoto, N. Chem. Pharm. Bull. 1976, 24, 960. (k) Roesler, P. P.; Kille, G.; Fleury, J.-P. Bull. Soc. Chim. Fr. 1967, 545.
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Sisko, J.1
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15
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see: (d) Sezen, B.; Sames, D. J. Am. Chem. Soc. 2003, 125, 5274. (e) Tan, K. L.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2002, 124, 13964. (f) Sisko, J.; Kassick, A. J.; Mellinger, M.; Filan, J. J.; Allen, A.; Olsen, M. A. J. Org. Chem. 2000, 65, 1516. (g) Sisko, J. J. Org. Chem. 1998, 63, 4529. (h) Groarke, M.; McKervey, M. A.; Nieuwenhuyzen, M. Tetrahedron Lett. 2000, 41, 1275. (i) Rolfs, A.; Liebscher, J. J. Org. Chem. 1997, 62, 3480. (j) Matsumura, K.; Kuritani, M.; Shimadzu, H.; Hashimoto, N. Chem. Pharm. Bull. 1976, 24, 960. (k) Roesler, P. P.; Kille, G.; Fleury, J.-P. Bull. Soc. Chim. Fr. 1967, 545.
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Groarke, M.1
McKervey, M.A.2
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0030995742
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see: (d) Sezen, B.; Sames, D. J. Am. Chem. Soc. 2003, 125, 5274. (e) Tan, K. L.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2002, 124, 13964. (f) Sisko, J.; Kassick, A. J.; Mellinger, M.; Filan, J. J.; Allen, A.; Olsen, M. A. J. Org. Chem. 2000, 65, 1516. (g) Sisko, J. J. Org. Chem. 1998, 63, 4529. (h) Groarke, M.; McKervey, M. A.; Nieuwenhuyzen, M. Tetrahedron Lett. 2000, 41, 1275. (i) Rolfs, A.; Liebscher, J. J. Org. Chem. 1997, 62, 3480. (j) Matsumura, K.; Kuritani, M.; Shimadzu, H.; Hashimoto, N. Chem. Pharm. Bull. 1976, 24, 960. (k) Roesler, P. P.; Kille, G.; Fleury, J.-P. Bull. Soc. Chim. Fr. 1967, 545.
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Liebscher, J.2
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see: (d) Sezen, B.; Sames, D. J. Am. Chem. Soc. 2003, 125, 5274. (e) Tan, K. L.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2002, 124, 13964. (f) Sisko, J.; Kassick, A. J.; Mellinger, M.; Filan, J. J.; Allen, A.; Olsen, M. A. J. Org. Chem. 2000, 65, 1516. (g) Sisko, J. J. Org. Chem. 1998, 63, 4529. (h) Groarke, M.; McKervey, M. A.; Nieuwenhuyzen, M. Tetrahedron Lett. 2000, 41, 1275. (i) Rolfs, A.; Liebscher, J. J. Org. Chem. 1997, 62, 3480. (j) Matsumura, K.; Kuritani, M.; Shimadzu, H.; Hashimoto, N. Chem. Pharm. Bull. 1976, 24, 960. (k) Roesler, P. P.; Kille, G.; Fleury, J.-P. Bull. Soc. Chim. Fr. 1967, 545.
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Kuritani, M.2
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see: (d) Sezen, B.; Sames, D. J. Am. Chem. Soc. 2003, 125, 5274. (e) Tan, K. L.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2002, 124, 13964. (f) Sisko, J.; Kassick, A. J.; Mellinger, M.; Filan, J. J.; Allen, A.; Olsen, M. A. J. Org. Chem. 2000, 65, 1516. (g) Sisko, J. J. Org. Chem. 1998, 63, 4529. (h) Groarke, M.; McKervey, M. A.; Nieuwenhuyzen, M. Tetrahedron Lett. 2000, 41, 1275. (i) Rolfs, A.; Liebscher, J. J. Org. Chem. 1997, 62, 3480. (j) Matsumura, K.; Kuritani, M.; Shimadzu, H.; Hashimoto, N. Chem. Pharm. Bull. 1976, 24, 960. (k) Roesler, P. P.; Kille, G.; Fleury, J.-P. Bull. Soc. Chim. Fr. 1967, 545.
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24
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1642479375
-
-
note
-
4, acetonitrile, 45°C) afforded imidoyl chloride in high yield. The cyclized product was not observed.
-
-
-
-
25
-
-
1642520146
-
-
note
-
4, acetonitrile, 45°C) afforded imidoyl chloride in high yield. The cyclized product was not observed.
-
-
-
-
27
-
-
1642520147
-
-
note
-
-
-
-
-
-
28
-
-
1642561057
-
-
note
-
4, acetonitrile, 45 °C) as determined by HPLC.
-
-
-
-
29
-
-
1642438363
-
-
note
-
31P NMR) at 0°C and room temperature were unsuccessful.
-
-
-
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31
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0029995822
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Matterson, D. S.; Man, H.-W., Ho, O. C. J. Am. Chem. Soc. 1996, 118, 4560.
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0037112673
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Littke, A.F.1
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(a) For a review of palladium-catalyzed coupling reactions of aryl chloride, see: Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176. (b) Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 1998, 37, 3387.
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