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Volumn 16, Issue 4, 2012, Pages 737-747

Synthesis and structure-behavior relationships of tetra-substituted imidazole derivatives of 1,3-diazabicyclo[3,1,0]hex-3-ene

Author keywords

1,3 Diazabicyclo 3.1.0 hex 3 ene; Ketoaziridine; Multicomponet reactions (MCRs); Photochromism; Structure photochromic behavior relationship (SPBR); Tetra substitutedimidazole

Indexed keywords

1 [4 (1,4,5 TRIPHENYL 1H IMIDAZOL 2 YL)PHENOXY]PROPAN 2 ONE; 1 [4 (4,5 DIPHENYL 1 PARA TOLYL 1H IMIDAZOL 2 YL)PHENOXY]PROPAN 2 ONE; 1 [4 [1 (4 ETHYLPHENYL) 4,5 DIPHENYL 1H IMIDAZOL 2YL]PHENOXY]PROPAN 2 ONE; 1 [4 [1 (4 METHOXYPHENYL) 4,5 DIPHENYL 1H IMIDAZOL 2YL]PHENOXY]PROPAN 2 ONE; 1 IODOPROPAN 2 ONE; 1,3 DIAZABICYCLO[3,1,0]HEX 3 ENE DERIVATIVE; 4 (1,4,5 TRIPHENYL 1H IMIDAZOL 2 YL)PHENOL; 4 (4,5 DIPHENYL 1 PARA TOLYL 1H IMIDAZOL 2 YL)PHENOL; 4 [1 (4 ETHYLPHENYL) 4,5 DIPHENYL 1H IMIDAZOL 2YL]PHENOL; 4 [1 (4 METHOXYPHENYL) 4,5 DIPHENYL 1H IMIDAZOL 2YL]PHENOL; 4 [[4 (1,4,5 TRIPHENYL 1H IMIDAZOL 2 YL)PHENOXY]METHYL] 4 METHYL 6 (3 NITROPHENYL) 2 PHENYL 3,5 DIAZA BICYCLO[3.1.0]HEX 2 ENE; 4 [[4 (1,4,5 TRIPHENYL 1H IMIDAZOL 2YL)PHENOXY]METHYL] 4 METHYL 6 (4 NITROPHENYL) 2 PHENYL 3,5 DIAZA BICYCLO[3.1.0]HEX 2 ENE; 4 [[4 (4,5 DIPHENYL 1 PARA TOLYL 1H IMIDAZOL 2 YL)PHENOXY]METHYL] 4 METHYL 6 (3 NITROPHENYL) 2 PHENYL 3,5 DIAZA BICYCLO[3.1.0]HEX 2 ENE; 4 [[4 (4,5 DIPHENYL 1 PARA TOLYL 1H IMIDAZOL 2YL)PHENOXY]METHYL] 4 METHYL 6 (4 NITROPHENYL 3,5 DIAZA BICYCLO[3.1.0]HEX 2 ENE; 4 [[4 [1 (3 ETHYLPHENYL) 4,5 DIPHENYL 1H IMIDAZOL 2 YL]PHENOXY]METHYL] 4 METHYL 6 (3 NITROPHENYL) 2 PHENYL 3,5 DIAZA BICYCL0[3.1.0]HEX 2 ENE; 4 [[4 [1 (4 ETHYLPHENYL) 4,5 DIPHENYL 1H IMIDAZOL 2 YL]PHENOXY]METHYL] 4 METHYL 6 (NITROPHENYL) 2 PHENYL 3,5 DIAZA BICYCLO[3.1.0]HEX 2 ENE; 4 [[4 [1 (4 METHOXYPHENYL) 4,5 DIPHENYL 1H IMIDAZOL 2YL]PHENOXY]METHYL] 4 METHYL 6 (3 NITROPHENYL) 2 PHENYL 3,5 DIAZA BICYCLO[3.1.0]HEX 2 ENE; 4 [[4 [1 (4 METHOXYPHENYL)4,5 DIPHENYL 1H IMIDAZOL 2 YL]PHENOXY]METHYL] 4 METHYL 6 (NITROPHENYL) 2 PHENYL 3,5 DIAZA BICYCLO[3.1.0]HEX 2 ENE; BIPHENYL; CYCLOHEXENE DERIVATIVE; IMIDAZOLE; IMIDAZOLE DERIVATIVE; UNCLASSIFIED DRUG; FUSED HETEROCYCLIC RINGS;

EID: 84878028536     PISSN: 13811991     EISSN: 1573501X     Source Type: Journal    
DOI: 10.1007/s11030-012-9409-7     Document Type: Article
Times cited : (14)

References (36)
  • 1
    • 0000096835 scopus 로고    scopus 로고
    • Click chemistry: Diverse chemical function from a few good reactions
    • 10.1002/1521-3773(20010601)40:11 <2004:AID-ANIE2004>3.0.CO;2-5 11433435 10.1002/1521-3773(20010601)40:11<2004: AID-ANIE2004>3.0.CO;2-5 1:CAS:528:DC%2BD3MXksVOis78%3D
    • Kolb HC, Finn MG, Sharpless KB (2001) Click chemistry: diverse chemical function from a few good reactions. Angew Chem Int Ed Engl 40: 2004-2021. doi: 10.1002/1521-3773(20010601)40:11<2004:AID-ANIE2004>3.0.CO;2-5
    • (2001) Angew Chem Int Ed Engl , vol.40 , pp. 2004-2021
    • Kolb, H.C.1    Finn, M.G.2    Sharpless, K.B.3
  • 2
    • 0035743613 scopus 로고    scopus 로고
    • Organic photochromism
    • 10.1351/pac200173040639 10.1351/pac200173040639 1:CAS:528: DC%2BD3MXltVyksrc%3D
    • Bouas-Laurent H, Durr H (2001) Organic photochromism. Pure Appl Chem 73: 639-665. doi: 10.1351/pac200173040639
    • (2001) Pure Appl Chem , vol.73 , pp. 639-665
    • Bouas-Laurent, H.1    Durr, H.2
  • 3
    • 0348080703 scopus 로고    scopus 로고
    • Diarylethenes for memories and switches
    • 10.1021/cr980069d 11777416 10.1021/cr980069d 1:CAS:528: DC%2BD3cXisFGitLc%3D
    • Irie M (2000) Diarylethenes for memories and switches. Chem Rev 100: 1685-1716. doi: 10.1021/cr980069d
    • (2000) Chem Rev , vol.100 , pp. 1685-1716
    • Irie, M.1
  • 4
    • 0344737904 scopus 로고    scopus 로고
    • Refractive index changes of amorphous diarylethenes containing 2,4-diphenylphenyl substituents
    • 10.1021/cm030304v 10.1021/cm030304v
    • Irie M, Kawai T, Kim MS, Maruyama H (2003) Refractive index changes of amorphous diarylethenes containing 2,4-diphenylphenyl substituents. Chem Mater 15: 4539-4543. doi: 10.1021/cm030304v
    • (2003) Chem Mater , vol.15 , pp. 4539-4543
    • Irie, M.1    Kawai, T.2    Kim, M.S.3    Maruyama, H.4
  • 6
    • 0003758823 scopus 로고
    • Wiley-Interscience New York
    • Brown GH (1971) Photochromism. Wiley-Interscience, New York
    • (1971) Photochromism
    • Brown, G.H.1
  • 9
    • 0000527186 scopus 로고    scopus 로고
    • In photochromism: Memories and switches
    • Irie M (2000) In photochromism: memories and switches. Chem Rev 100:1683-1890
    • (2000) Chem Rev , vol.100 , pp. 1683-1890
    • Irie, M.1
  • 11
    • 0003464709 scopus 로고    scopus 로고
    • Organic photochromic and thermochromic compounds
    • Crano JC, Guglielmetti RJ (eds) Plenum Press, New York
    • Inouye M (1999) Organic photochromic and thermochromic compounds. In: Crano JC, Guglielmetti RJ (eds) Physicochemical studies, biological applications, and thermochromism. Plenum Press, New York, pp 393-414
    • (1999) Physicochemical Studies, Biological Applications, and Thermochromism , pp. 393-414
    • Inouye, M.1
  • 12
    • 0037128543 scopus 로고    scopus 로고
    • Digital processing and communication with molecular switches
    • DOI 10.1002/1521-4095(20020318)14:6 <401::AID-ADMA401>3.0.CO;2-F
    • Raymo FM (2002) Digital processing and communication with molecular switches. Adv Mater 14: 401-414. doi: 10.1002/1521-4095(20020318)14:6<401:: AID-ADMA401>3.0.CO;2-F (Pubitemid 34266018)
    • (2002) Advanced Materials , vol.14 , Issue.6 , pp. 401-414
    • Raymo, F.M.1
  • 13
    • 1242300126 scopus 로고    scopus 로고
    • Molecular scale logic gates
    • 10.1002/chem.200305054 14767921 10.1002/chem.200305054
    • De Silva AP, Mcclenaghan ND (2004) Molecular scale logic gates. Chem Eur J 10: 574-586. doi: 10.1002/chem.200305054
    • (2004) Chem Eur J , vol.10 , pp. 574-586
    • De Silva, A.P.1    McClenaghan, N.D.2
  • 14
    • 2942581418 scopus 로고    scopus 로고
    • Molecular logic gates based on pentacyanoferrate complexes: From simple gates to three-dimensional logic systems
    • 10.1002/chem.200305663 15146524 10.1002/chem.200305663
    • Szaciłowski K (2004) Molecular logic gates based on pentacyanoferrate complexes: from simple gates to three-dimensional logic systems. Chem Eur J 10: 2520-2528. doi: 10.1002/chem.200305663
    • (2004) Chem Eur J , vol.10 , pp. 2520-2528
    • Szaciłowski, K.1
  • 15
    • 28244438389 scopus 로고    scopus 로고
    • A multi-photo responsive photochromic dithienylethene containing coumarin derivative
    • DOI 10.1016/j.tetlet.2005.10.102, PII S0040403905023348
    • Huang C, Li F, Xiao S, Yi T (2005) A multi-photo responsive photochromic dithienylethene containing Coumarin derivative. Tetrahedron Lett 46: 9009-9012. doi: 10.1016/j.tetlet.2005.10.102 (Pubitemid 41711865)
    • (2005) Tetrahedron Letters , vol.46 , Issue.52 , pp. 9009-9012
    • Xiao, S.1    Yi, T.2    Li, F.3    Huang, C.4
  • 16
    • 84890758526 scopus 로고    scopus 로고
    • Photoswitched and functionalized oligothiophenes: Synthesis and photochemical and electrochemical properties
    • 10.1002/chem.19960021112 10.1002/chem.19960021112
    • Lehn JM, Tsivgoulius GM (1996) Photoswitched and functionalized oligothiophenes: synthesis and photochemical and electrochemical properties. Chem Eur J 2: 1399-1406. doi: 10.1002/chem.19960021112
    • (1996) Chem Eur J , vol.2 , pp. 1399-1406
    • Lehn, J.M.1    Tsivgoulius, G.M.2
  • 17
    • 0032704971 scopus 로고    scopus 로고
    • Optical switching and fluorescence modulation properties of photochromic metal complexes derived from dithienylethene ligands
    • Fernandez-Acebes A, Lehn JM (1999) Optical switching and fluorescence modulation properties of photochromic metal complexes derived from dithienylethene ligands. Chem Eur J 5: 3285-3292. doi: 10.1002/(SICI)1521- 3765(19991105)5:11<3285::AID-CHEM3285>3.0.CO;2-Q (Pubitemid 129611774)
    • (1999) Chemistry - A European Journal , vol.5 , Issue.11 , pp. 3285-3292
    • Fernandez-Acebes, A.1    Lehn, J.-M.2
  • 18
    • 0035838885 scopus 로고    scopus 로고
    • Synthesis of fluorescent diarylethenes having a 2,4,5-triphenylimidazole chromophore
    • DOI 10.1021/jo010267w
    • Irie M, Soong CF, Yagi K (2001) Synthesis of fluorescent diarylethenes having a 2,4,5-triphenylimidazole chromophore. J Org Chem 66: 5419-5423. doi: 10.1021/jo010267w (Pubitemid 32884145)
    • (2001) Journal of Organic Chemistry , vol.66 , Issue.16 , pp. 5419-5423
    • Yagi, K.1    Chai Fong Soong2    Irie, M.3
  • 19
    • 0016259815 scopus 로고
    • Preparation and antiinflammatory activity of some nonacidic trisubstituted imidazoles
    • 10.1021/jm00257a011 10.1021/jm00257a011
    • Lambardino JG, Wiseman EH (1974) Preparation and antiinflammatory activity of some nonacidic trisubstituted imidazoles. J Med Chem 17: 1182-1188. doi: 10.1021/jm00257a011
    • (1974) J Med Chem , vol.17 , pp. 1182-1188
    • Lambardino, J.G.1    Wiseman, E.H.2
  • 20
    • 33845335883 scopus 로고    scopus 로고
    • Antinociceptive and antiinflammatory activities and QSAR studies on 2-substituted-4,5-diphenyl-1H-imidazoles
    • DOI 10.1016/j.bmc.2006.10.025, PII S0968089606008467
    • Doble M, Puratchikody A (2007) Antinociceptive and antiinflammatory activities and QSAR studies on 2-substituted-4,5-diphenyl-1H-imidazoles. Bioorg Med Chem 15: 1083-1090. doi: 10.1016/j.bmc.2006.10.025 (Pubitemid 44880696)
    • (2007) Bioorganic and Medicinal Chemistry , vol.15 , Issue.2 , pp. 1083-1090
    • Puratchikody, A.1    Doble, M.2
  • 23
    • 77953686438 scopus 로고    scopus 로고
    • Room temperature synthesis of tri-, tetrasubstituted imidazoles and bis-Analogues by mercaptopropylsilica (MPS) in aqueous methanol: Application to the synthesis of the drug trifenagrel
    • 10.1016/j.tetlet.2010.05.102 10.1016/j.tetlet.2010.05.102
    • Drew MGB, Mukhopadhyay C, Tapaswi PK (2010) Room temperature synthesis of tri-, tetrasubstituted imidazoles and bis-Analogues by mercaptopropylsilica (MPS) in aqueous methanol: application to the synthesis of the drug trifenagrel. Tetrahedron Lett 51: 3944-3950. doi: 10.1016/j.tetlet.2010.05.102
    • (2010) Tetrahedron Lett , vol.51 , pp. 3944-3950
    • Drew, M.G.B.1    Mukhopadhyay, C.2    Tapaswi, P.K.3
  • 24
    • 77955845356 scopus 로고    scopus 로고
    • Synthesis and photochromic behavior of mono-, and biphotochromic system linked by p-phenylene bridge
    • 10.1016/j.cclet.2010.04.036 10.1016/j.cclet.2010.04.036
    • Ghavidast A, Mahmoodi NO, Tabatabaeian K (2010) Synthesis and photochromic behavior of mono-, and biphotochromic system linked by p-phenylene bridge. Chin Chem Lett 21: 1199-1202. doi: 10.1016/j.cclet.2010.04.036
    • (2010) Chin Chem Lett , vol.21 , pp. 1199-1202
    • Ghavidast, A.1    Mahmoodi, N.O.2    Tabatabaeian, K.3
  • 25
    • 77149147412 scopus 로고    scopus 로고
    • Photochromic behavior of several new synthesized dyes via zincke salts
    • 10.1002/poc.1623
    • Arvand M., Fesanghari M, Ghanadzadeh A, Mahmoodi NO, Mamaghani M (2010) Photochromic behavior of several new synthesized dyes via zincke salts. J Phys Org Chem 23: 266-270. doi: 10.1002/poc.1623
    • (2010) J Phys Org Chem , vol.23 , pp. 266-270
    • Arvand, M.1    Fesanghari, M.2    Ghanadzadeh, A.3    Mahmoodi, N.O.4    Mamaghani, M.5
  • 26
    • 77955725537 scopus 로고    scopus 로고
    • NMR structural elucidation and photochromic behavior of new 1,3-diazabicyclo[3.1.0]hex-3-ene derivatives
    • 10.1134/S1070428010060175 10.1134/S1070428010060175
    • Arvand M, Kiyani H, Mahmoodi NO, Sharifzadeh B, Tabatabaeian K, Zanjanchi MA (2010) NMR structural elucidation and photochromic behavior of new 1,3-diazabicyclo[3.1.0]hex-3-ene derivatives. Rus J Org Chem 46: 884-889. doi: 10.1134/S1070428010060175
    • (2010) Rus J Org Chem , vol.46 , pp. 884-889
    • Arvand, M.1    Kiyani, H.2    Mahmoodi, N.O.3    Sharifzadeh, B.4    Tabatabaeian, K.5    Zanjanchi, M.A.6
  • 27
    • 65949109941 scopus 로고    scopus 로고
    • Photochromic behavior of several new synthesized bis-1,3-diazabicyclo[3. 1.0]hex-3-ene
    • 10.1002/poc.1550 10.1002/poc.1550 1:CAS:528:DC%2BD1MXltlCht78%3D
    • Kiyani H, Mahmoodi NO, Tabatabaeian K, Zanjanchi MA (2009) Photochromic behavior of several new synthesized bis-1,3-diazabicyclo[3.1.0]hex-3-ene. J Phys Org Chem 22: 559-567. doi: 10.1002/poc.1550
    • (2009) J Phys Org Chem , vol.22 , pp. 559-567
    • Kiyani, H.1    Mahmoodi, N.O.2    Tabatabaeian, K.3    Zanjanchi, M.A.4
  • 28
    • 67650756374 scopus 로고    scopus 로고
    • Synthesis and photochromism of 1,3-diazabicyclo[3.1.0]hex-3-ene phenol rings
    • 10.1016/j.mencom.2009.07.010 10.1016/j.mencom.2009.07.010 1:CAS:528:DC%2BD1MXhtVGnsbvF
    • Kiyani H, Mahmoodi NO, Tabatabaeian K, Zanjanchi MA (2009) Synthesis and photochromism of 1,3-diazabicyclo[3.1.0]hex-3-ene phenol rings. Mendeleev Commun 19: 203-205. doi: 10.1016/j.mencom.2009.07.010
    • (2009) Mendeleev Commun , vol.19 , pp. 203-205
    • Kiyani, H.1    Mahmoodi, N.O.2    Tabatabaeian, K.3    Zanjanchi, M.A.4
  • 29
    • 34548564197 scopus 로고    scopus 로고
    • Synthesis and photochromic properties of new heterocyclic derivatives of 1,3-diazabicyclo[3.1.0]hex-3-ene
    • Kiyani H, Mahmoodi NO, Sharifzadeh B, Yazdanbakhsh MR (2007) Synthesis and photochromic properties of new heterocyclic derivatives of 1,3-diazabicyclo[3.1.0]hex-3-ene. J Chin Chem Soc 54: 635-641
    • (2007) J Chin Chem Soc , vol.54 , pp. 635-641
    • Kiyani, H.1    Mahmoodi, N.O.2    Sharifzadeh, B.3    Yazdanbakhsh, M.R.4
  • 30
    • 3943076413 scopus 로고    scopus 로고
    • Photochro-mism of several synthesised 1,3-diazabicyclo[3,1,0]hex-3-ene derivatives
    • doi: 10.3184/0308234041423772
    • Kiyani H, Mahmoodi NO, Zanjanchi MA (2004) Photochro-mism of several synthesised 1,3-diazabicyclo[3,1,0]hex-3-ene derivatives. J Chem Res Synop 6: 438-440. doi: 10.3184/0308234041423772
    • (2004) J Chem Res Synop , vol.6 , pp. 438-440
    • Kiyani, H.1    Mahmoodi, N.O.2    Ma, Z.3
  • 31
    • 4644326806 scopus 로고    scopus 로고
    • Synthesis of thiophene derivatives of 1,3-diazabicyclo[3,1,0] hex-3-ene
    • 10.5012/bkcs.2004.25.9.1417 10.5012/bkcs.2004.25.9.1417
    • Kiyani H, Mahmoodi NO (2004) Synthesis of thiophene derivatives of 1,3-diazabicyclo[3,1,0] hex-3-ene. Bull Korean Chem Soc 25: 1417-1420. doi: 10.5012/bkcs.2004.25.9.1417
    • (2004) Bull Korean Chem Soc , vol.25 , pp. 1417-1420
    • Kiyani, H.1    Mahmoodi, N.O.2
  • 32
    • 84859054323 scopus 로고    scopus 로고
    • Two 1,3-diazabicyclo [3.1.0]hex-3-enes with a tripod-core
    • 10.1002/hlca.201100333 10.1002/hlca.201100333 1:CAS:528: DC%2BC38XktV2gsro%3D
    • Mahmoodi NO, Kiyani H, Tabatabaeian K (2012) Two 1,3-diazabicyclo [3.1.0]hex-3-enes with a tripod-core. Helv Chim Acta 95: 536-542. doi: 10.1002/hlca.201100333
    • (2012) Helv Chim Acta , vol.95 , pp. 536-542
    • Mahmoodi, N.O.1    Kiyani, H.2    Tabatabaeian, K.3
  • 33
    • 40849117943 scopus 로고    scopus 로고
    • 2: An efficient reagent system for the one-pot synthesis of 1,2,4,5-tetrasubstituted imidazoles
    • 10.1016/j.tetlet.2008.02.100 10.1016/j.tetlet.2008.02.100
    • 2: an efficient reagent system for the one-pot synthesis of 1,2,4,5-tetrasubstituted imidazoles. Tetrahedron Lett 49: 2575-2577. doi: 10.1016/j.tetlet.2008.02.100
    • (2008) Tetrahedron Lett , vol.49 , pp. 2575-2577
    • Hashemi, M.M.1    Mirjalili, B.F.2    Sadeghi, B.3
  • 34
    • 33947279845 scopus 로고    scopus 로고
    • 2O): A mild and efficient reusable catalyst for the one-pot synthesis of 1,2,4,5-tetrasubstituted imidazoles under conventional heating and microwave irradiation
    • DOI 10.1016/j.molcata.2006.10.056, PII S1381116906013628
    • 2O): a mild and efficient reusable catalyst for the one-pot synthesis of 1,2,4,5-tetrasubstituted imidazoles under conventional heating and microwave irradiation. J Mol Catal A 266: 104-108. doi: 10.1016/j.molcata.2006.10.056 (Pubitemid 46415740)
    • (2007) Journal of Molecular Catalysis A: Chemical , vol.266 , Issue.1-2 , pp. 104-108
    • Nagarapu, L.1    Apuri, S.2    Kantevari, S.3
  • 35
    • 0001142888 scopus 로고
    • Practical method for the asymmetric synthesis of indolizidine alkaloids: Total synthesis of(-)-monomorine i
    • 10.1021/jo00205a023 10.1021/jo00205a023 1:CAS:528:DyaL2MXhtFektL0%3D
    • Royer J, Husson HP (1985) Practical method for the asymmetric synthesis of indolizidine alkaloids: total synthesis of(-)-monomorine I. J Org Chem 50: 670-673. doi: 10.1021/jo00205a023
    • (1985) J Org Chem , vol.50 , pp. 670-673
    • Royer, J.1    Husson, H.P.2
  • 36
    • 35548965056 scopus 로고    scopus 로고
    • Highly efficient and clean method for direct α-iodination of aromatic ketones
    • DOI 10.1055/s-2007-983880
    • Yin G, Gao M, She N, She S, Wu A, Pan Y (2007) Highly efficient and clean method for direct α-iodination of aromatic ketones. Synthesism 20: 3113-3116. doi: 10.1055/s-2007-83880 (Pubitemid 350013354)
    • (2007) Synthesis , Issue.20 , pp. 3113-3116
    • Yin, G.1    Gao, M.2    She, N.3    Hu, S.4    Wu, A.5    Pan, Y.6


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