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Goodman, K. B.; Cui, H.; Dowdell, S. E.; Gaitanopoulos, D. E.; Ivy, R. L.; Sehon, C. A.; Stavenger, R. A.; Wang, G. Z.; Viet, A. Q.; Xu, W.; Ye, G.; Semus, S. F.; Evans, C.; Fries, H. E.; Jolivette, L. J.; Kirkpatrick, R. B.; Dul, E.; Khandekar, S. S.; Yi, T.; Jung, D. K.; Wright, L. L.; Smith, G. K.; Behm, D. J.; Bentley, R.; Doe, C. P.; Hu, E.; Lee, D. J. Med. Chem. 2007, 50, 6.
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11
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33645529315
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For some other references for the synthesis of indazolone analogues, see
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(a) Mills, A. D.; Nazer, M. Z.; Haddadin, M. J.; Kurth, M. J. J. Org. Chem. 2006, 71, 2687. For some other references for the synthesis of indazolone analogues, see:
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Mills, A.D.1
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33845273049
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For a recent example for copper-catalyzed intramolecular C-N coupling reaction, see
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(a) For a recent example for copper-catalyzed intramolecular C-N coupling reaction, see: Lu, H.; Li, C. Org. Lett. 2006, 8, 5365.
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Lu, H.1
Li, C.2
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35548992379
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During the preparation of this manuscript, Zhu and co-workers disclosed their studies on the synthesis of 2-aryl-2H-indazoles via copper(I)-catalyzed intramolecular amination reaction of N'-aryl-N'-(o- bromobenzyl) acetylhydrazines, but the reaction need higher reaction temperature (100-105 °C) and long reaction time (20 h) in a pressure tube. See: Liu, R.; Zhu, Y.; Qin, L.; Ji, S.; Katayama, S. Heterocycles 2007, 71, 1755.
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(b) During the preparation of this manuscript, Zhu and co-workers disclosed their studies on the synthesis of 2-aryl-2H-indazoles via copper(I)-catalyzed intramolecular amination reaction of N'-aryl-N'-(o- bromobenzyl) acetylhydrazines, but the reaction need higher reaction temperature (100-105 °C) and long reaction time (20 h) in a pressure tube. See: Liu, R.; Zhu, Y.; Qin, L.; Ji, S.; Katayama, S. Heterocycles 2007, 71, 1755.
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18
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49649120027
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The acid hydrazides were synthesized from corresponding acid chloride with hydrazine or the condensation of 2-halobenzoic acid with hydrazine using EDC
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The acid hydrazides were synthesized from corresponding acid chloride with hydrazine or the condensation of 2-halobenzoic acid with hydrazine using EDC.
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19
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20844435969
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(a) Zhang, H.; Cai, Q.; Ma, D. J. Org. Chem. 2005, 70, 5164.
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(b) Ma, D.; Cai, Q.; Zhang, H. Org. Lett. 2003, 5, 2453.
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Ma, D.1
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0035804329
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Selwood, D. L.; Brummell, D. G.; Budworth, J.; Burtin, G. E.; Campbell, R. O.; Ghana, S. S.; Charles, I. G.; Fernandez, P. A.; Glen, R. C.; Goggin, M. C.; Hobbs, A. J.; Kling, M. R.; Liu, Q.; Madge, D. J.; Meillerais, S.; Powell, K. L.; Reynolds, K.; Spacey, G. D.; Stables, J. N.; Tatlock, M. A.; Wheeler, K. A.; Wishart, G.; Woo, C.-K. J. Med. Chem. 2001, 44, 78.
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Selwood, D.L.1
Brummell, D.G.2
Budworth, J.3
Burtin, G.E.4
Campbell, R.O.5
Ghana, S.S.6
Charles, I.G.7
Fernandez, P.A.8
Glen, R.C.9
Goggin, M.C.10
Hobbs, A.J.11
Kling, M.R.12
Liu, Q.13
Madge, D.J.14
Meillerais, S.15
Powell, K.L.16
Reynolds, K.17
Spacey, G.D.18
Stables, J.N.19
Tatlock, M.A.20
Wheeler, K.A.21
Wishart, G.22
Woo, C.-K.23
more..
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33745962425
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For a recent example for copper-catalyzed C-N coupling reactions at room temperature, see
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For a recent example for copper-catalyzed C-N coupling reactions at room temperature, see: Shafir, A.; Buchwald, S. L. J. Am. Chem. Soc. 2006, 128, 8742.
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J. Am. Chem. Soc
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Shafir, A.1
Buchwald, S.L.2
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23
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33845579450
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Xie, X.; Chen, Y.; Ma, D. J. Am. Chem. Soc. 2006, 128, 16050.
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Xie, X.1
Chen, Y.2
Ma, D.3
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24
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49649123388
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Typical Experimental Procedure, Synthesis of 1-tert- butyl-1,2-dihydroindazol-3-one The mixture of 2-iodobenzoic acid N'-iert-butylhydrazide (0.32 g, 1.0 mmol, CuI (19 mg, 0.10 mmol, 10 mol, L-proline (23 mg, 0.20 mmol, 20 mol, and K2CO3 (0.28 g, 2.0 mmol) in DMSO (10 mL) was stirred at r.t. for 3 h under nitrogen atmosphere. The mixture was treated with H2O and the mixture was extracted three times with EtOAc. The combined organic layer was washed with H2O and brine, and dried over MgSO4. After filtration, solvent was evaporated in vacuo to ca. 1 mL and crystallization afforded 1-tert-butyl-1,2-dihydroindazole-3-one (0.19 g, 97, as white crystals. Rf= 0.36 (hexane-EtOAc, 1:1, mp 115-117 °C. IR (KBr, 2979 (NH, 1648 (C=O, 1538, 1209, 748 cm-1. 1H NMR (400 MHz, DMSO, δ, 10.47 (br s, 1 H, NH, 7.61 (d, 1 H, J= 8.5 Hz, C-4, 7.59 d, 1 H, J
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2O 191.1179; found: 191.1182.
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25
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49649102185
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Acid hydrazide derived from 2,4,6-trichlorophenyl-hydrazine, tert-butylcarbazide, benzoylhydrazine, and p- toluenesulfonylhydrazine did not afford the corresponding indazolone to recover the starting material even at heating conditions (>100 °C).
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Acid hydrazide derived from 2,4,6-trichlorophenyl-hydrazine, tert-butylcarbazide, benzoylhydrazine, and p- toluenesulfonylhydrazine did not afford the corresponding indazolone to recover the starting material even at heating conditions (>100 °C).
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27
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49649117337
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A variety of compounds possessing pharmaceutical profile have been prepared from indazolone derivatives, see ref. 15
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A variety of compounds possessing pharmaceutical profile have been prepared from indazolone derivatives, see ref. 15.
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