메뉴 건너뛰기




Volumn 14, Issue 2, 2010, Pages 249-256

The application of poly(N, N'-dibromo-N-ethyl-benzene-1, 3-disulfonamide) and N, N, N', N'-tetrabromobenzene-1, 3-disulfonamide as catalysts for one-pot synthesis of 2-aryl-1-arylmethyl-1H-1,3-benzimidazoles and 1,5-benzodiazepines, and new reagents for synthesis of benzimidazoles

Author keywords

1,5 Benzodiazepines; Benzimidazoles; O Phenylenediamine; PBBS; TBBDA

Indexed keywords

1,2 PHENYLENEDIAMINE; 1,5 BENZODIAZEPINE; 2 ARYL 1 ARYLMETHYL 1H 1,3 BENZIMIDAZOLE; BENZODIAZEPINE DERIVATIVE; IMIDAZOLE DERIVATIVE; N,N,N',N' TETRABROMOBENZENE 1,3 DISULFONAMIDE; POLY(N,N' DIBROMO N ETHYL BENZENE 1,3 DISULFONAMIDE); UNCLASSIFIED DRUG; BENZENE DERIVATIVE; BENZIMIDAZOLE DERIVATIVE; SULFONAMIDE;

EID: 77954665534     PISSN: 13811991     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11030-009-9169-1     Document Type: Article
Times cited : (37)

References (34)
  • 1
    • 0001414741 scopus 로고
    • Comprehensive organic chemistry
    • In: Barton D, Ollis WD (ed), Pergamon, Oxford
    • Smalley RK (1979) Comprehensive organic chemistry. In: Barton D, Ollis WD (ed) Comprehensive organic chemistry, vol 4. Pergamon, Oxford, p 600
    • (1979) Comprehensive Organic Chemistry , vol.4 , pp. 600
    • Smalley, R.K.1
  • 2
    • 0001277441 scopus 로고
    • Isolation and properties of crystalline cobamide coenzymes containing benzimidazole or 5,6-dimethylbenzimidazole
    • Barker HA, Smyth RD,Weissbach H, Toohey JI, Ladd JN, Volcani BE (1960) Isolation and properties of crystalline cobamide coenzymes containing benzimidazole or 5,6-dimethylbenzimidazole. J Biol Chem 235: 480-488
    • (1960) J Biol Chem , vol.235 , pp. 480-488
    • Barker, H.A.1    Smyth, R.D.2    Weissbach, H.3    Toohey, J.I.4    Ladd, J.N.5    Volcani, B.E.6
  • 3
    • 0037043196 scopus 로고    scopus 로고
    • Efficient telomerization of 1,3-butadiene with alcohols in the presence of in situ generated palladium(0)carbene complexes
    • PII: S1381-1169(02)00068-7
    • Jackstell A, Frisch A, BellerM, Rottger D, Malaun M, Bildstein B (2002) Efficient telomerization of 1,3-butadiene with alcohols in the presence of in situ generated palladium(0)carbene complexes. J Mol Catal A Chem 185: 105-112. PII: S1381-1169(02)00068-77
    • (2002) J Mol Catal A Chem , vol.185 , pp. 105-112
    • Jackstell, A.1    Frisch, A.2    BellerM Rottger, D.3    Malaun, M.4    Bildstein, B.5
  • 4
    • 23844456602 scopus 로고    scopus 로고
    • Solvent-controlled selective synthesis of a trans-configured benzimidazoline-2-ylidene palladium(II) complex and investigations of its Heck-type catalytic activity
    • DOI 10.1016/j.jorganchem.2005.04.053, PII S0022328X0500402X
    • Huynh HV, Ho JHH, Neo TC, Koh LL (2005) Solvent-controlled selective synthesis of a trans-configured benzimidazoline- 2-ylidene palladium(II) complex and investigations of its Heck-type catalytic activity. J Organomet Chem 690:3854-3860. doi:10.1016/j.jorganchem.2005.04.053 (Pubitemid 41162577)
    • (2005) Journal of Organometallic Chemistry , vol.690 , Issue.16 , pp. 3854-3860
    • Huynh, H.V.1    Ho, J.H.H.2    Neo, T.C.3    Koh, L.L.4
  • 5
    • 33751157540 scopus 로고
    • DNAdirected alkylating agents. 6. Synthesis and antitumor activity of DNA minor groove-targeted aniline mustard analogs of pibenzimol (Hoechst 33258)
    • doi:10.1021/ jm00051a010
    • Gravatt GL, Baguley BC, Wilson WR, Denny WA (1994) DNAdirected alkylating agents. 6. Synthesis and antitumor activity of DNA minor groove-targeted aniline mustard analogs of pibenzimol (Hoechst 33258). J Med Chem 37:4338-4345. doi:10.1021/ jm00051a010
    • (1994) J Med Chem , vol.37 , pp. 4338-4345
    • Gravatt, G.L.1    Baguley, B.C.2    Wilson, W.R.3    Denny, W.A.4
  • 6
    • 0001325629 scopus 로고    scopus 로고
    • Substituted 2,5'-bi-1H-benzimidazoles: Topoisomerase I inhibition and cytotoxicity
    • DOI 10.1021/jm950412w
    • Kim JS, Gatto B, Yu C, Liu A, Liu LF, Lavoie EJ (1996) Substituted 2,5'-bi-1H-benzimidazoles: topoisomerase I inhibition and cytotoxicity. J Med Chem 39:992-998. doi:10.1021/jm950412w (Pubitemid 26069790)
    • (1996) Journal of Medicinal Chemistry , vol.39 , Issue.4 , pp. 992-998
    • Jung Sun Kim1    Gatto, B.2    Yu, C.3    Liu, A.4    Liu, L.F.5    LaVoie, E.J.6
  • 7
    • 0031463691 scopus 로고    scopus 로고
    • Synthesis and biological activity of novel nonnucleoside inhibitors of HIV-1 reverse transcriptase. 2-Aryl-substituted benzimidazoles
    • DOI 10.1021/jm970096g
    • Rott T, Morningstar ML, Boyer PL, Hughes SH, Buckheit RWC (1997) Synthesis and biological activity of novel nonnucleoside inhibitors of HIV-1 reverse transcriptase. 2-Aryl-substituted benzimidazoles. J Med Chem 40:4199-4207. doi:10.1021/jm970096g (Pubitemid 28042301)
    • (1997) Journal of Medicinal Chemistry , vol.40 , Issue.26 , pp. 4199-4207
    • Roth, T.1    Morningstar, M.L.2    Boyer, P.L.3    Hughes, S.H.4    Buckheit Jr., R.W.5    Michejda, C.J.6
  • 8
    • 0035687467 scopus 로고    scopus 로고
    • Traceless solid-phase synthesis of 5-benzoylbenzimidazoles
    • doi:10. 1139/cjc-79-11-1556
    • Lee KJ, Janda KD (2001) Traceless solid-phase synthesis of 5-benzoylbenzimidazoles. Can J Chem 79:1556-1561. doi:10. 1139/cjc-79-11-1556
    • (2001) Can J Chem , vol.79 , pp. 1556-1561
    • Lee, K.J.1    Janda, K.D.2
  • 9
    • 0000586488 scopus 로고    scopus 로고
    • Oxidation with metal oxides-II: Oxidation of chalcone phenylhydrazones, pyrazolines, o-aminobenzylidine anils and o-hydroxy benzylidine anils with manganese dioxide
    • doi:10.1016/0040-4020(68)88080-9
    • Bhatnagar I, George MV (1998) Oxidation with metal oxides-II: Oxidation of chalcone phenylhydrazones, pyrazolines, o-aminobenzylidine anils and o-hydroxy benzylidine anils with manganese dioxide. Tetrahedron 24:1293-1298. doi:10.1016/ 0040-4020(68)88080-88089
    • (1998) Tetrahedron , vol.24 , pp. 1293-1298
    • Bhatnagar, I.1    George, M.V.2
  • 10
    • 33846488082 scopus 로고    scopus 로고
    • Advances in microwave-assisted combinatorial chemistry without polymer-supported reagents
    • DOI 10.1007/s11030-006-9021-9
    • Martinez-Palou R (2006) Advances in microwave-assisted combinatorial chemistry without polymer-supported reagents. Mol Divers 10: 435-462. doi:10.1007/s11030-006-9021-9 (Pubitemid 46150638)
    • (2006) Molecular Diversity , vol.10 , Issue.3 , pp. 435-462
    • Martinez-Palou, R.1
  • 11
    • 36549075194 scopus 로고    scopus 로고
    • Synthesis of 2-substituted benzimidazoles and bis-benzimidazoles by microwave in the presence of alumina-methanesulfonic acid
    • Niknam K, Fatehi-Raviz A (2007) Synthesis of 2-substituted benzimidazoles and bis-benzimidazoles by microwave in the presence of alumina-methanesulfonic acid. J Iran Chem Soc 4:438-443
    • (2007) J Iran Chem Soc , vol.4 , pp. 438-443
    • Niknam, K.1    Fatehi-Raviz, A.2
  • 12
    • 33947688826 scopus 로고    scopus 로고
    • A rapid and efficient synthesis of benzimidazoles using hypervalent iodine as oxidant
    • DOI 10.1055/s-2007-965922
    • Du LH,WangYG(2007)Arapid and efficient synthesis of benzimidazoles using hypervalent iodine as oxidant. Synthesis 5:675-678. doi:10.1055/s-2007-965922 (Pubitemid 46486571)
    • (2007) Synthesis , Issue.5 , pp. 675-678
    • Du, L.-H.1    Wang, Y.-G.2
  • 13
    • 4143104652 scopus 로고    scopus 로고
    • Ytterbium triflate promoted synthesis of benzimidazole derivatives
    • doi:10.1055/s-2004-829555
    • Curini M, Epifano F, Montanari F, Rosati O, Taccone S (2004) Ytterbium triflate promoted synthesis of benzimidazole derivatives. Synlett 10:1832-1834. doi:10.1055/s-2004-829555
    • (2004) Synlett , vol.10 , pp. 1832-1834
    • Curini, M.1    Epifano, F.2    Montanari, F.3    Rosati, O.4    Taccone, S.5
  • 14
    • 33947541193 scopus 로고    scopus 로고
    • A simple and efficient one-pot synthesis of 2-substituted benzimidazoles
    • DOI 10.1055/s-2007-965878
    • Bahrami K, Khodaei MM, Kavianinia I (2007) A simple and efficient one-pot synthesis of 2-substituted benzimidazoles. Synthesis 4:547-550. doi:10.1055/s-2007-965878 (Pubitemid 46474199)
    • (2007) Synthesis , Issue.4 , pp. 547-550
    • Bahrami, K.1    Khodaei, M.M.2    Kavianinia, I.3
  • 15
    • 33644879165 scopus 로고    scopus 로고
    • Selective synthesis of 2-aryl-1-arylmethyl-1H-1,3-benzimidazoles in water at ambient temperature
    • DOI 10.1016/j.tetlet.2006.02.049, PII S0040403906003029
    • Salehi P, Dabiri M, Zolfigol MA, Otokesh S, Baghbanzadeh M (2006) Selective synthesis of 2-aryl-1-arylmethyl-1H-1,3- benzimidazoles in water at ambient temperature. Tetrahedron Lett 47:2557-2560. doi:10.1016/j.tetlet.2006. 02.049 (Pubitemid 43383939)
    • (2006) Tetrahedron Letters , vol.47 , Issue.15 , pp. 2557-2560
    • Salehi, P.1    Dabiri, M.2    Zolfigol, M.A.3    Otokesh, S.4    Baghbanzadeh, M.5
  • 16
    • 34948893906 scopus 로고    scopus 로고
    • One-pot efficient synthesis of 2-aryl-1-arylmethyl-1H-benzimidazoles and 2,4,5-triaryl-1H-imidazoles using oxalic acid catalyst
    • DOI 10.1055/s-2007-983872
    • Kokare ND, Jaiprakash NS, Devanand BS (2007) One-pot efficient synthesis of 2-aryl-1-arylmethyl-1H-benzimidazoles and 2,4,5- triaryl-1H-imidazoles using oxalic acid catalyst. Synthesis 18:2829-2834. doi:10.1055/s-2007-983872 (Pubitemid 47528863)
    • (2007) Synthesis , Issue.18 , pp. 2829-2834
    • Kokare, N.D.1    Sangshetti, J.N.2    Shinde, D.B.3
  • 17
    • 2342454576 scopus 로고    scopus 로고
    • 2O promoted one-pot expeditious and convenient synthesis of 2-substituted benzimidazoles and 3,1,5-benzoxadiazepines
    • doi:10. 1016/j.tetlet.2004.03.117
    • 2O promoted one-pot expeditious and convenient synthesis of 2-substituted benzimidazoles and 3,1,5-benzoxadiazepines. Tetrahedron Lett 45:4185-4187. doi:10. 1016/j.tetlet.2004.03.117
    • (2004) Tetrahedron Lett , vol.45 , pp. 4185-4187
    • Tandon, V.K.1    Kumar, M.2
  • 18
    • 12144260094 scopus 로고
    • New synthesis of dihydro- and tetrahydro-l,5-benzodiazepines by reductive condensation of o-phenylenediamine and ketones in the presence of sodium borohydride
    • doi:10.3987/ R-1986-01-0135
    • Morales HR, Bulbarela A, Contreras R (1986) New synthesis of dihydro- and tetrahydro-l,5-benzodiazepines by reductive condensation of o-phenylenediamine and ketones in the presence of sodium borohydride. Heterocycles 24:135-139. doi:10.3987/ R-1986-01-0135
    • (1986) Heterocycles , vol.24 , pp. 135-139
    • Morales, H.R.1    Bulbarela, A.2    Contreras, R.3
  • 20
    • 0035808949 scopus 로고    scopus 로고
    • A simple and new method for the synthesis of 1,5-benzodiazepine derivatives on a solid surface
    • doi:10.1016/ S0040-4039(00)02168-7
    • Balakrishna MS, Kaboudin B (2001) A simple and new method for the synthesis of 1,5-benzodiazepine derivatives on a solid surface. Tetrahedron Lett 42: 1127-1129. doi:10.1016/ S0040-4039(00)02168-7
    • (2001) Tetrahedron Lett , vol.42 , pp. 1127-1129
    • Balakrishna, M.S.1    Kaboudin, B.2
  • 21
    • 0035972003 scopus 로고    scopus 로고
    • Ytterbium triflate promoted synthesis of 1,5-benzodiazepine derivatives
    • doi:10.1016/ S0040-4039(01)00413-0
    • Currini M, Epifano F, Marcotullio MC, Rosati O (2001) Ytterbium triflate promoted synthesis of 1,5-benzodiazepine derivatives. Tetrahedron Lett 42: 3193-3195. doi:10.1016/ S0040-4039(01)00413-0
    • (2001) Tetrahedron Lett , vol.42 , pp. 3193-3195
    • Currini, M.1    Epifano, F.2    Marcotullio, M.C.3    Rosati, O.4
  • 22
    • 0001324345 scopus 로고    scopus 로고
    • Alumina/phosphorus pentoxide (APP) as an efficient reagent for the synthesis of 1,5-benzodiazepines under microwave irradiation
    • doi:10.3987/COM-01-9253
    • Kaboudin B, Navaee K (2001) Alumina/phosphorus pentoxide (APP) as an efficient reagent for the synthesis of 1,5-benzodiazepines under microwave irradiation. Heterocycles 55:1443-1447. doi:10.3987/COM-01-9253
    • (2001) Heterocycles , vol.55 , pp. 1443-1447
    • Kaboudin, B.1    Navaee, K.2
  • 23
    • 0037170153 scopus 로고    scopus 로고
    • An efficient method for the synthesis of 1,5-benzodiazepine derivatives under microwave irradiation without solvent
    • DOI 10.1016/S0040-4039(02)00115-6, PII S0040403902001156
    • Minothora P, Julia SS, Constaninos AT (2002) An efficient method for the synthesis of 1,5-benzodiazepine derivatives under microwave irradiation without solvent. Tetrahedron Lett 43:1755-1758. doi:10.1016/S0040-4039(02)00115-6 (Pubitemid 34169693)
    • (2002) Tetrahedron Letters , vol.43 , Issue.9 , pp. 1755-1758
    • Pozarentzi, M.1    Stephanidou-Stephanatou, J.2    Tsoleridis, C.A.3
  • 24
    • 33750287620 scopus 로고    scopus 로고
    • NBS as an efficient catalyst for the synthesis of 1,5-benzodiazepine derivatives under mild conditions
    • doi:10.1016/j. tetlet.2006.09.128
    • Chun-Wei K, Shivaji VM, Chinf-Fa Y (2006) NBS as an efficient catalyst for the synthesis of 1,5-benzodiazepine derivatives under mild conditions. Tetrahedron Lett 47:8523-8528. doi:10.1016/j. tetlet.2006.09.128
    • (2006) Tetrahedron Lett , vol.47 , pp. 8523-8528
    • Chun-Wei, K.1    Shivaji, V.M.2    Chinf-Fa, Y.3
  • 25
    • 19944401847 scopus 로고    scopus 로고
    • Molecular-iodine-catalyzed one-pot synthesis of 1,5-benzodiazepine derivatives under solvent-free conditions
    • DOI 10.1055/s-2005-868516, U06405ST
    • Wei-Yi C, Jun L (2005) Molecular-iodine-catalyzed one-pot synthesis of 1,5-benzodiazepine derivatives under solvent-free conditions. Synlett 1337-1339. doi:10.1055/s-2005-868516 (Pubitemid 40755322)
    • (2005) Synlett , Issue.8 , pp. 1337-1339
    • Chen, W.-Y.1    Lu, J.2
  • 26
    • 33744951715 scopus 로고    scopus 로고
    • An efficient synthesis of 1,5-benzadiazepine derivatives catalyzed by silver nitrate
    • DOI 10.1039/b601993e
    • Kumar R, Chaudhary P, Nimesh S, Verma AK, Chandra R (2006) An efficient synthesis of 1,5-benzadiazepine derivatives catalyzed by silver nitrate. Green Chem 8:519-521. doi:10.1039/b601993e (Pubitemid 43856604)
    • (2006) Green Chemistry , vol.8 , Issue.6 , pp. 519-521
    • Kumar, R.1    Chaudhary, P.2    Nimesh, S.3    Verma, A.K.4    Chandra, R.5
  • 27
    • 33750208479 scopus 로고    scopus 로고
    • Catalytic synthesis of 2,3-dihydro-1H-1,5-benzodiazepines by ferric perchlorate
    • doi:10.1016/j. molcata.2006.06.013
    • Heravi MM, Zadsirjan V, Behbahani FK, Oskooie HA (2006) Catalytic synthesis of 2,3-dihydro-1H-1,5-benzodiazepines by ferric perchlorate. J Mol Catal Chem 259:201-204. doi:10.1016/j. molcata.2006.06.013
    • (2006) J Mol Catal Chem , vol.259 , pp. 201-204
    • Heravi, M.M.1    Zadsirjan, V.2    Behbahani, F.K.3    Oskooie, H.A.4
  • 28
    • 0037463420 scopus 로고    scopus 로고
    • Room temperature ionic liquid promoted synthesis of 1,5-benzodiazepine derivatives under ambient conditions
    • DOI 10.1016/S0040-4039(03)00096-0, PII S0040403903000960
    • Jarikote DV, Siddiqui SA, Rajagopal R, Thomas D, Lahoti RJ (2003) Room temperature ionic liquid promoted synthesis of 1,5-benzodiazepine derivatives under ambient conditions. Tetrahedron Lett 44:1835-1838. doi:10.1016/S0040- 4039(03)00096-0 (Pubitemid 36183413)
    • (2003) Tetrahedron Letters , vol.44 , Issue.9 , pp. 1835-1838
    • Jarikote, D.V.1    Siddiqui, S.A.2    Rajagopal, R.3    Daniel, T.4    Lahoti, R.J.5    Srinivasan, K.V.6
  • 29
    • 18744375223 scopus 로고    scopus 로고
    • Mild and regioselective bromination of aromatic compounds with N, N, N', N'-tetrabromobenzene-1,3-disulfonylamide and poly(N-bromobenzene- 1,3-disulfonylamide)
    • doi:10. 1055/s-2005-861851
    • Ghorbani-Vaghei R, Jalili H (2005) Mild and regioselective bromination of aromatic compounds with N, N, N', N'-tetrabromobenzene-1,3-disulfonylamide and poly(N-bromobenzene- 1,3-disulfonylamide). Synthesis 7:1099-1102. doi:10. 1055/s-2005-861851
    • (2005) Synthesis , vol.7 , pp. 1099-1102
    • Ghorbani-Vaghei, R.1    Jalili, H.2
  • 30
    • 33646774340 scopus 로고    scopus 로고
    • Poly(N-bromobenzene-1,3-disulfonamide) and N, N, N0, N0- tetrabromobenzene-1,3-disulfonamide as novel catalytic reagents for silylation of alcohols, phenols, and thiols using hexamethyldisilazane
    • doi:10.1016/j.tetlet.2006. 03.157
    • Ghorbani-Vaghei R, Zolfigol MA, Chegeny M, Veisi H (2006) Poly(N-bromobenzene-1,3-disulfonamide) and N, N, N0, N0- tetrabromobenzene-1,3- disulfonamide as novel catalytic reagents for silylation of alcohols, phenols, and thiols using hexamethyldisilazane. Tetrahedron Lett 47:4505-4508. doi:10.1016/j.tetlet.2006. 03.157
    • (2006) Tetrahedron Lett , vol.47 , pp. 4505-4508
    • Ghorbani-Vaghei, R.1    Zolfigol, M.A.2    Chegeny, M.3    Veisi, H.4
  • 31
    • 33744475661 scopus 로고    scopus 로고
    • Simple, convenient and heterogeneous method for conversion of urazoles to triazolinediones using N,N,N′,N′-tetrabromobenzene-1,3- disulfonylamide or trichloromelamine under mild and heterogeneous conditions
    • DOI 10.1055/s-2006-926446
    • Zolfigol MA, Ghorbani-Vaghei R, Mallakpour S, Chehardoli G, Ghorbani Choghamani A, Yazdi Hosain A (2006) Simple, convenient and heterogeneous method for conversion of urazoles to triazolinediones using N, N, N', N'-tetrabromobenzene-1,3-disulfonylamide or trichloromelamine under mild and heterogeneous conditions. Synthesis 10:1631-1634. doi:10.1055/s-2006-926446 (Pubitemid 43805969)
    • (2006) Synthesis , Issue.10 , pp. 1631-1634
    • Zolfigol, M.A.1    Ghorbani-Vaghei, R.2    Mallakpour, S.3    Chehardoli, G.4    Choghamarani, A.G.5    Yazdi, A.H.6
  • 32
    • 26844484610 scopus 로고    scopus 로고
    • N,N′-Diiodo-N,N′-1,2-ethanediylbis(p-toluenesulfonamide) as a reagent for conversion of aldehydes to methyl esters
    • DOI 10.1070/MC2005v015n05ABEH002091
    • Ghorbani-Vaghei R, Shahbazee E, Veisi H (2005) N, N'-Diiodo- N, N'-1,2-ethanediylbis(p-toluenesulfonamide) as a reagent for conversion of aldehydes to methyl esters. Mendeleev Commun 15:207-208. doi:10.1070/ MC2005v015n05ABEH002091 (Pubitemid 41463260)
    • (2005) Mendeleev Communications , Issue.5 , pp. 207-208
    • Ghorbani-Vaghei, R.1    Shahbazee, E.2    Veisi, H.3
  • 33
    • 5344232753 scopus 로고    scopus 로고
    • N, N'-Dibromo- N, N'-1,2-ethanediylbis(p-toluenesulphonamide) as a useful reagent for oxidation of 1,3,5-trisubstituted pyrazolines
    • Ghorbani-VagheiR,Azarifar D, MalekiB (2004) N, N'-Dibromo- N, N'-1,2-ethanediylbis(p-toluenesulphonamide) as a useful reagent for oxidation of 1,3,5-trisubstituted pyrazolines. Bull Korean Chem Soc 25: 953-954
    • (2004) Bull Korean Chem Soc , vol.25 , pp. 953-954
    • Ghorbani-Vaghei, R.1    Azarifar, D.2    Maleki, B.3
  • 34
    • 15044358965 scopus 로고    scopus 로고
    • NBS-catalyzed hydroamination and hydroalkoxylation of activated styrenes
    • DOI 10.1021/ol047402m
    • Talluri SK, Sudalai A (2005) NBS-catalyzed hydroamination and hydroalkoxylation of activated styrenes. Org Lett 7:855-857. doi:10.1021/ol047402m (Pubitemid 40380243)
    • (2005) Organic Letters , vol.7 , Issue.5 , pp. 855-857
    • Talluri, S.K.1    Sudalai, A.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.