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1
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0004273844
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For some reviews on imidazole synthesis, see: a, Academic Press, Inc, San Diego, CA
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For some reviews on imidazole synthesis, see: (a) Grimmett, M. R. Imidazole and Benzimidazote Synthesis; Academic Press, Inc.: San Diego, CA, 1997.
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Imidazole and Benzimidazote Synthesis
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Grimmett, M.R.1
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65549134628
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Katritzky, A. R, Ramsden, C. A, Scriven, E. F. V, Taylor, R. J. K, Eds, Pergamon Press: Oxford
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(b) Grimmett, M. R. In Comprehensive Heterocyclic Chemistry III; Katritzky, A. R., Ramsden, C. A., Scriven, E. F. V., Taylor, R. J. K., Eds.; Pergamon Press: Oxford, 2008; Vol. 4, pp 143-364.
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Comprehensive Heterocyclic Chemistry III
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Grimmett, M.R.1
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(d) Du, H.; He, Y.; Rasapalli, S.; Lovely, C. J. Synlett 2006, 7, 965-992.
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Synlett
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Du, H.1
He, Y.2
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(e) Bellina, F.; Cauteruccio, S.; Rossi, R. Tetrahedron 2007, 63, 4571-4624.
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Tetrahedron
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Bellina, F.1
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7
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16444367024
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For reviews on biological activities of imidazoles, see: a
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For reviews on biological activities of imidazoles, see: (a) Bolani, M.; Gonzalez, M. Mini-Rev. Med. Chem. 2005, 5, 409-424.
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(b) Jin, Z. Nat. Prod. Rep. 2006, 23, 464-496.
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Nat. Prod. Rep
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Jin, Z.1
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9
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34248587434
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For some recent examples, see: a
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For some recent examples, see: (a) Lovely, C. J.; Du, H.; Sivappa, R.; Bhandari, M. R.; He, Y.; Dias, H. V. R. J. Org. Chem. 2007, 72, 3741-3749.
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J. Org. Chem
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Lovely, C.J.1
Du, H.2
Sivappa, R.3
Bhandari, M.R.4
He, Y.5
Dias, H.V.R.6
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10
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2942672496
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(b) He, Y.; Chen, Y.; Du, H.; Schmid, L. A.; Lovely, C. J. Tetrahedron Lett. 2004, 45, 5529-5532.
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(2004)
Tetrahedron Lett
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He, Y.1
Chen, Y.2
Du, H.3
Schmid, L.A.4
Lovely, C.J.5
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11
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51549107027
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For a personal example, see Supporting Information
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For a personal example, see Supporting Information.
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12
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0035356729
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(a) MacNeil, S. L.; Familoni, O. B.; Snieckus, V. J. Org. Chem. 2001, 66, 3662-3670.
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J. Org. Chem
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MacNeil, S.L.1
Familoni, O.B.2
Snieckus, V.3
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13
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0000021853
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(b) Watanabe, H.; Schwarz, R. A.; Hauser, C. R.; Lewis, J.; Slocum, D. W. Can. J. Chem. 1969, 47, 1543-1546.
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Can. J. Chem
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Watanabe, H.1
Schwarz, R.A.2
Hauser, C.R.3
Lewis, J.4
Slocum, D.W.5
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18
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37049077716
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(e) Katritzky, A. R.; Slawinski, J. J.; Brunner, F. J. Chem. Soc., Perkin Trans. 1 1989, 1139-1145.
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Katritzky, A.R.1
Slawinski, J.J.2
Brunner, F.3
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20
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24944528300
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(a) Lee, H. K.; Bang, M.; Pak, C. S. Tetrahedron Lett. 2005, 46, 7139-7142.
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(2005)
Tetrahedron Lett
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Lee, H.K.1
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Pak, C.S.3
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(b) Beaudoin, S.; Kinsey, K. E.; Burns, J. F. J. Org. Chem. 2003, 68, 115-119.
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J. Org. Chem
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Beaudoin, S.1
Kinsey, K.E.2
Burns, J.F.3
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22
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0041629071
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For punctual examples of 1,5-substituted imidazole synthesis using a similar strategy with other protecting groups, see: a
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For punctual examples of 1,5-substituted imidazole synthesis using a similar strategy with other protecting groups, see: (a) Chandana, P.; Nayyar, A.; Jain, R. Synth. Commun. 2003, 33, 2925-2933.
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(2003)
Synth. Commun
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Chandana, P.1
Nayyar, A.2
Jain, R.3
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25
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0034163052
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Bhagavatula, L.; Premchandran, R. H.; Plata, D. J.; King, S. A.; Morton, H. E. Heterocycles 2000, 53, 729-732.
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Heterocycles
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Bhagavatula, L.1
Premchandran, R.H.2
Plata, D.J.3
King, S.A.4
Morton, H.E.5
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26
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51549113513
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US 2005250948, 460319
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(a) Jones, T. K.; Mani, N. US 2005250948, 2005; Chem. Abstr. 2005, 143, 460319.
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Chem. Abstr
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Jones, T.K.1
Mani, N.2
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27
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51549117422
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WO 2002079168, 279192
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(b) Bogenstaetter, M.; Carruthers, N. I.; Lovenberg, T. W.; Ly, K. S.; Jablonowski, J. A. WO 2002079168, 2002; Chem. Abstr. 2002, 137, 279192.
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Chem. Abstr
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Bogenstaetter, M.1
Carruthers, N.I.2
Lovenberg, T.W.3
Ly, K.S.4
Jablonowski, J.A.5
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28
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33744944765
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For some examples of metal-catalyzed coupling involving 4- or 5-iodoimidazoles, see: ref 1c. (a) Yang, X.; Knochel, P. Chem. Commun. 2006, 2170-2172.
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For some examples of metal-catalyzed coupling involving 4- or 5-iodoimidazoles, see: ref 1c. (a) Yang, X.; Knochel, P. Chem. Commun. 2006, 2170-2172.
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30
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0041520600
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(c) Yoshida, T.; Nishiyachi, M.; Nakashima, N.; Murase, M.; Kotani, E. Chem. Pharm. Bull. 2003, 51, 209-214.
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Chem. Pharm. Bull
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Yoshida, T.1
Nishiyachi, M.2
Nakashima, N.3
Murase, M.4
Kotani, E.5
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31
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(d) Lovely, C. J.; Du, H.; Dias, H. V. R. Org. Lett. 2001, 3, 1319-1322.
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Org. Lett
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Du, H.2
Dias, H.V.R.3
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(e) Kawasaki, I.; Katsuma, H.; Nakayama, Y.; Yamashita, M.; Ohta, S. Heterocycles 1998, 48, 1887-1901.
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Heterocycles
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Kawasaki, I.1
Katsuma, H.2
Nakayama, Y.3
Yamashita, M.4
Ohta, S.5
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33
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(f) Carver, D. S.; Lindell, S. D.; Saville-Stones, E. A. Tetrahedron 1997, 53, 14481-14496.
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Tetrahedron
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Carver, D.S.1
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Saville-Stones, E.A.3
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35
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0036929504
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(a) Moreno, P.; Heras, M.; Maestro, M.; Villagordo, J. M. Synthesis 2002, 18, 2691-2700.
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(2002)
Synthesis
, vol.18
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Moreno, P.1
Heras, M.2
Maestro, M.3
Villagordo, J.M.4
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36
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(b) Schickaneder, H.; Engler, H.; Szelenyi, I. J. Med. Chem. 1987, 30, 547-551.
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J. Med. Chem
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Schickaneder, H.1
Engler, H.2
Szelenyi, I.3
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37
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51549098095
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Neither isomerization nor degradation was observed after 4 months at, 18°C
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Neither isomerization nor degradation was observed after 4 months at - 18°C
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38
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51549112424
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For both structures determined by X-ray diffraction analysis in this paper, 10 and 18, two independent molecules are observed in the asymmetric parts of the unit cell; they differ only by a slight different orientation of the phenyl group. The bond lengths indicate clearly a greater conjugation in the imidazole ring of 10 as compared to 18
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For both structures determined by X-ray diffraction analysis in this paper, 10 and 18, two independent molecules are observed in the asymmetric parts of the unit cell; they differ only by a slight different orientation of the phenyl group. The bond lengths indicate clearly a greater conjugation in the imidazole ring of 10 as compared to 18.
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39
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51549096090
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As a comparison, methylation of corresponding N-deprotected imidazole leads to a 57/43 mixture of 1,2,4- and 1,2,5-isomers (see Supporting Information).
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As a comparison, methylation of corresponding N-deprotected imidazole leads to a 57/43 mixture of 1,2,4- and 1,2,5-isomers (see Supporting Information).
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41
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51549114792
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2 for 3 days in the presence of 0.3 equiv of the base. Conversely, formation of 13 is observed when stirring 10 in the presence of molecular sieve. (18) Once formed, the salt 14 may as well catalyze isomerization of 10.
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2 for 3 days in the presence of 0.3 equiv of the base. Conversely, formation of 13 is observed when stirring 10 in the presence of molecular sieve. (18) Once formed, the salt 14 may as well catalyze isomerization of 10.
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42
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51549115570
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It has been noted that purity of reactants and solvent is crucial for reproducibility of this experiment (see Supporting Information, 20) The reaction was also tried under classical thermal conditions heating bath, but it was found to be much slower and leading to more side products
-
It has been noted that purity of reactants and solvent is crucial for reproducibility of this experiment (see Supporting Information). (20) The reaction was also tried under classical thermal conditions (heating bath), but it was found to be much slower and leading to more side products.
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43
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0034679644
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Blass, B. E.; Huang, C. T.; Kawamoto, R. M.; Li, M.; Liu, S.; Portlock, D. E.; Rennels, W. M.; Simmons, M. Bioorg. Med. Chem. Lett. 2000, 10, 1543-1545.
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Bioorg. Med. Chem. Lett
, vol.10
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Blass, B.E.1
Huang, C.T.2
Kawamoto, R.M.3
Li, M.4
Liu, S.5
Portlock, D.E.6
Rennels, W.M.7
Simmons, M.8
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44
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51549109450
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4 was purchased from Acros and purified prior to use following the procedure described by: Curphey, T. J. Org. Synth. 1971, 51, 142-147.
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4 was purchased from Acros and purified prior to use (following the procedure described by: Curphey, T. J. Org. Synth. 1971, 51, 142-147.
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