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Volumn , Issue 13, 2008, Pages 1973-1976

Copper-catalyzed mild and efficient entry to 1-substituted indazolones

Author keywords

Copper; Coupling; Hydrazide; Indazolone; Proline

Indexed keywords

1 INDAZOLONE DERIVATIVE; 2 HALOBENZOHYDRAZIDE; COPPER; INDAZOLE DERIVATIVE;

EID: 49649107515     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/S-2008-1077973     Document Type: Article
Times cited : (29)

References (27)
  • 11
    • 33645529315 scopus 로고    scopus 로고
    • For some other references for the synthesis of indazolone analogues, see
    • (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:
    • (2006) J. Org. Chem , vol.71 , pp. 2687
    • Mills, A.D.1    Nazer, M.Z.2    Haddadin, M.J.3    Kurth, M.J.4
  • 16
    • 33845273049 scopus 로고    scopus 로고
    • For a recent example for copper-catalyzed intramolecular C-N coupling reaction, see
    • (a) For a recent example for copper-catalyzed intramolecular C-N coupling reaction, see: Lu, H.; Li, C. Org. Lett. 2006, 8, 5365.
    • (2006) Org. Lett , vol.8 , pp. 5365
    • Lu, H.1    Li, C.2
  • 17
    • 35548992379 scopus 로고    scopus 로고
    • 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.
    • (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.
  • 18
    • 49649120027 scopus 로고    scopus 로고
    • The acid hydrazides were synthesized from corresponding acid chloride with hydrazine or the condensation of 2-halobenzoic acid with hydrazine using EDC
    • The acid hydrazides were synthesized from corresponding acid chloride with hydrazine or the condensation of 2-halobenzoic acid with hydrazine using EDC.
  • 22
    • 33745962425 scopus 로고    scopus 로고
    • For a recent example for copper-catalyzed C-N coupling reactions at room temperature, see
    • 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.
    • (2006) J. Am. Chem. Soc , vol.128 , pp. 8742
    • Shafir, A.1    Buchwald, S.L.2
  • 24
    • 49649123388 scopus 로고    scopus 로고
    • 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
    • 2O 191.1179; found: 191.1182.
  • 25
    • 49649102185 scopus 로고    scopus 로고
    • 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).
    • 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).
  • 27
    • 49649117337 scopus 로고    scopus 로고
    • A variety of compounds possessing pharmaceutical profile have been prepared from indazolone derivatives, see ref. 15
    • A variety of compounds possessing pharmaceutical profile have been prepared from indazolone derivatives, see ref. 15.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.