메뉴 건너뛰기




Volumn 17, Issue 7, 2012, Pages 8674-8686

Ultrasound-promoted one-pot, three-component synthesis of spiro[indoline-3,1′-pyrazolo[1,2-b]phthalazine] derivatives

Author keywords

1 pyrazolo 1; 2 b phthalazine ; Multicomponent; Spiro indoline 3; Spirooxindole; Ultrasound

Indexed keywords

INDOLE DERIVATIVE; INDOLINE; ISATIN; PHTHALAZINE; PHTHALAZINE DERIVATIVE; PYRAZOLE DERIVATIVE; SPIRO COMPOUND;

EID: 84864632966     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules17078674     Document Type: Article
Times cited : (29)

References (46)
  • 2
    • 2542509173 scopus 로고    scopus 로고
    • Multicomponent Reactions with Isocyanides
    • Dömling, A.; Ugi, I. Multicomponent Reactions with Isocyanides. Angew. Chem. Int. Ed. Engl. 2000, 39, 3168-3210.
    • (2000) Angew. Chem. Int. Ed. Engl , vol.39 , pp. 3168-3210
    • Dömling, A.1    Ugi, I.2
  • 3
    • 31544434530 scopus 로고    scopus 로고
    • Recent developments in isocyanide based multicomponent reactions in applied chemistry
    • DOI 10.1021/cr0505728
    • Dömling, A. Recent Developments in Isocyanide Based Multicomponent Reactions in Applied Chemistry. Chem. Rev. 2006, 106, 17-89. (Pubitemid 43159621)
    • (2006) Chemical Reviews , vol.106 , Issue.1 , pp. 17-89
    • Domling, A.1
  • 5
    • 57549100677 scopus 로고    scopus 로고
    • Highly regioselective synthesis of polysubstituted pyrroles through three-component reaction induced by low-valent titanium reagent
    • Dou, G.L.; Shi, C.L.; Shi, D.Q. Highly Regioselective Synthesis Of Polysubstituted Pyrroles Through Three-Component Reaction Induced By Low-Valent Titanium Reagent. J. Comb. Chem. 2008, 10, 810-813.
    • (2008) J. Comb. Chem , vol.10 , pp. 810-813
    • Dou, G.L.1    Shi, C.L.2    Shi, D.Q.3
  • 6
    • 74049124482 scopus 로고    scopus 로고
    • Silica gel-catalyzed one-pot syntheses in water and fluorescence properties studies of 5-amino-2-aryl- 3H-chromeno[4,3,2-de][1,6]naphthyridine-4- carbonitriles and 5-amino-2-aryl-3H-quinolino[4,3,2- de][1,6]naphthyridine-4- carbonitriles
    • Wu, H.; Lin, W.; Wan, Y.; Xin, H.Q.; Shi, D.Q.; Shi, Y.H.; Yuan, R.; Bo, R.C.; Yin, W. Silica gel-catalyzed one-pot syntheses in water and fluorescence properties studies of 5-amino-2-aryl- 3H-chromeno[4,3,2-de][1,6]naphthyridine-4- carbonitriles and 5-amino-2-aryl-3H-quinolino[4,3,2- de][1,6]naphthyridine-4- carbonitriles. J. Comb. Chem. 2010, 12, 31-34.
    • (2010) J. Comb. Chem , vol.12 , pp. 31-34
    • Wu, H.1    Lin, W.2    Wan, Y.3    Xin, H.Q.4    Shi, D.Q.5    Shi, Y.H.6    Yuan, R.7    Bo, R.C.8    Yin, W.9
  • 7
    • 77949397767 scopus 로고    scopus 로고
    • Efficient one-pot synthesis of spirooxindole derivatives catalyzed by l-proline in aqueous medium
    • Li, Y.L.; Chen, H.; Shi, C.L.; Shi, D.Q.; Ji, S.J. Efficient One-Pot Synthesis of Spirooxindole Derivatives Catalyzed By L-Proline In Aqueous Medium. J. Comb. Chem. 2010, 12, 231-237.
    • (2010) J. Comb. Chem , vol.12 , pp. 231-237
    • Li, Y.L.1    Chen, H.2    Shi, C.L.3    Shi, D.Q.4    Ji, S.J.5
  • 9
    • 0020066039 scopus 로고
    • Biologically active indole derivatives
    • Joshi, K.C.; Chand, P. Biologically active indole derivatives. Pharmazie 1982, 37, 1-12. (Pubitemid 12113974)
    • (1982) Pharmazie , vol.37 , Issue.1 , pp. 1-12
    • Joshi, C.1    Chand, P.2
  • 10
    • 0035594725 scopus 로고    scopus 로고
    • The chemistry of isatins: A review from 1975 to 1999
    • Da-Silva, J.F.M.; Garden, S.J.; Pinto, A.C. The chemistry of isatins: A review from 1975 to 1999. J. Braz. Chem. Soc. 2001, 12, 273-324.
    • J. Braz. Chem. Soc , vol.2001 , Issue.12 , pp. 273-324
    • Da-Silva, J.F.M.1    Garden, S.J.2    Pinto, A.C.3
  • 11
    • 1842767304 scopus 로고    scopus 로고
    • Synthesis and evaluation of some new spiro indoline-based heterocycles as potentially active antimicrobial agents
    • DOI 10.1016/j.bmc.2003.10.063, PII S096808960400121X
    • Abdel-Rahman, A.H.; Keshk, E.M.; Hanna, M.A.; El-Bady, S.M. Synthesis and evaluation of some new spiro indoline-based heterocycles as potentially active antimicrobial agents. Bioorg. Med. Chem. 2004, 12, 2483-2488. (Pubitemid 38471731)
    • (2004) Bioorganic and Medicinal Chemistry , vol.12 , Issue.9 , pp. 2483-2488
    • Abdel-Rahman, A.H.1    Keshk, E.M.2    Hanna, M.A.3    El-Bady, Sh.M.4
  • 13
    • 16644375516 scopus 로고    scopus 로고
    • Javaniside, a novel DNA cleavage agent from Alangium javanicum having an unusual oxindole skeleton
    • Ma, J.; Hecht, S.M. Javaniside, a novel DNA cleavage agent from Alangium javanicum having an unusual oxindole skeleton. Chem. Commun. 2004, 1190-1191. (Pubitemid 38797468)
    • (2004) Chemical Communications , Issue.10 , pp. 1190-1191
  • 14
    • 0032143275 scopus 로고    scopus 로고
    • Tryprostatin A, a specific and novel inhibitor of microtubule assembly
    • Usui, T.; Kondoh, M.; Cui, C.B.; Mayumi, T.; Osada, H. Tryprostatin A, a specific and novel inhibitor of microtubule assembly. Biochem. J. 1998, 333, 543-548. (Pubitemid 28398519)
    • (1998) Biochemical Journal , vol.333 , Issue.3 , pp. 543-548
    • Usui, T.1    Kondoh, M.2    Cui, C.-B.3    Mayumi, T.4    Osada, H.5
  • 15
    • 0036754283 scopus 로고    scopus 로고
    • Synthesis of halogen derivatives of benzo[h]chromene and benzo[a]anthracene with promising antimicrobial activities
    • DOI 10.1016/S0014-827X(02)01263-6, PII S0014827X02012636
    • Khafagy, M.M.; El-Wahas, A.H.F.A.; Eid, F.A.; El-Agrody, A.M. Synthesis of halogen derivatives of benzo[h]chromene and benzo[a]anthracene with promising antimicrobial activities. Farmaco 2002, 57, 715-722. (Pubitemid 35287005)
    • (2002) Farmaco , vol.57 , Issue.9 , pp. 715-722
    • Khafagy, M.M.1    Abd El-Wahab, A.H.F.2    Eid, F.A.3    El-Agrody, A.M.4
  • 16
    • 74049137845 scopus 로고    scopus 로고
    • Pseudo four-component synthesis of a spiro[diindeno[1,2-b:2,1-e]pyridine- 11,3-indoline]-trione library
    • Ghahremanzadeh, R.; Sayyafi, M.; Ahadi, S.; Bazgir, A. One-Pot, Pseudo four-component synthesis of a spiro[diindeno[1,2-b:2?,1?-e]pyridine-11,3?- indoline]-trione library. J. Comb. Chem. 2010, 12, 191-194.
    • (2010) J. Comb. Chem , vol.12 , pp. 191-194
    • Ghahremanzadeh, R.1    Sayyafi, M.2    Ahadi, S.3    One-Pot, B.A.4
  • 17
    • 0342325087 scopus 로고
    • The chemistry of the phthalazines
    • Vaughan, W.R. The Chemistry of the Phthalazines. Chem. Rev. 1948, 43, 447-508.
    • (1948) Chem. Rev , vol.43 , pp. 447-508
    • Vaughan, W.R.1
  • 18
    • 0023923956 scopus 로고
    • The acylating potential of -lactam antibacterials: Base hydrolysis of bicyclic pyrazolidinones
    • Indelicato, J.M.; Pasini, C.E. The Acylating Potential of -Lactam Antibacterials: Base Hydrolysis of Bicyclic Pyrazolidinones. J. Med. Chem. 1988, 31, 1227-1230.
    • (1988) J. Med. Chem , vol.31 , pp. 1227-1230
    • Indelicato, J.M.1    Pasini, C.E.2
  • 19
    • 0001294552 scopus 로고
    • Reactions of some 1-alkyl- and 1,1-dialkyl-1H-diazirino[1,2- b]phthalazine-3,8-diones
    • Heine, H.W. Diaziridines. III. Reactions of some 1-alkyl- and 1,1-dialkyl-1H-diazirino[1,2- b]phthalazine-3,8-diones. J. Org. Chem. 1974, 39, 3187-3191.
    • (1974) J. Org. Chem , vol.39 , pp. 3187-3191
    • Heine, H.W.1    Iii, Diaziridines.2
  • 20
    • 0016710549 scopus 로고
    • Chemie des cis-trioxa-tris-σ-homobenzoles. eine einfche totalsynthese des streptamines
    • Schwesinger, R.; Prinzbach, H. Chemie des cis-Trioxa-tris-σ- homobenzoles. Eine einfche Totalsynthese des Streptamines. Angew. Chem. 1975, 87, 625-626.
    • (1975) Angew. Chem , vol.87 , pp. 625-626
    • Schwesinger, R.1    Prinzbach, H.2
  • 21
    • 84987318409 scopus 로고
    • The syntheses of pyridazino[1,2-A] pyridazine derivatives of furan, Pyridazine and pyrrole by Diels-Alder reactions
    • Gillis, B.T.; Valentour, J.C. The syntheses of pyridazino[1,2-a] pyridazine derivatives of furan, Pyridazine and pyrrole by Diels-Alder reactions. J. Heterocycl. Chem. 1971, 8, 13-17.
    • (1971) J. Heterocycl. Chem , vol.8 , pp. 13-17
    • Gillis, B.T.1    Valentour, J.C.2
  • 22
    • 0027185364 scopus 로고    scopus 로고
    • Synthesis of (±)tetrahydromyricoidine
    • Song, J.G.; Hesse, M. Synthesis of (±)tetrahydromyricoidine. Tetrahedron 2008, 49, 6797-6799.
    • (2008) Tetrahedron , vol.49 , pp. 6797-6799
    • Song, J.G.1    Hesse, M.2
  • 23
    • 0025876946 scopus 로고
    • Chain length dependent reactivity of 2-(ω-hydroxyalkyl)-4- (ω-hydroxyalkylamino)phthalazin-1(2H)-ones in azeotropic hydrobromic acid
    • Csampai, A.; Krmendy, K.; Ruff, F. Chain length dependent reactivity of 2-(ω-hydroxyalkyl)-4- (ω-hydroxyalkylamino)phthalazin-1(2H)-ones in azeotropic hydrobromic acid. Tetrahedron 1991, 47, 4457-4464.
    • (1991) Tetrahedron , vol.47 , pp. 4457-4464
    • Csampai, A.1    Körmendy, K.2    Ruff, F.3
  • 24
    • 33749521397 scopus 로고    scopus 로고
    • One-pot three-component reaction of isocyanides, dialkyl acetylenedicarboxylates and phthalhydrazide: Synthesis of highly functionalized 1H-pyrazolo[1,2-b]phthalazine-5,10-diones
    • DOI 10.1016/j.tet.2006.09.006, PII S0040402006014396
    • Teimouri, M.B. One-pot three-component reaction of isocyanides, Dialkyl acetylenedicarboxylates and phthalhydrazide: Synthesis of highly functionalized 1H-pyrazolo[1,2-b]phthalazine-5,10-diones. Tetrahedron 2006, 62, 10849-10853. (Pubitemid 44528646)
    • (2006) Tetrahedron , vol.62 , Issue.47 , pp. 10849-10853
    • Teimouri, M.B.1
  • 25
    • 77952712196 scopus 로고    scopus 로고
    • An Efficient one-pot synthesis of novel pyrazolophthalazinyl spirooxindoles
    • Shanthi, G.; Perumal, P.T. An Efficient one-pot synthesis of novel pyrazolophthalazinyl spirooxindoles. J. Chem. Sci. 2010, 122, 415-421.
    • (2010) J. Chem. Sci , vol.122 , pp. 415-421
    • Shanthi, G.1    Perumal, P.T.2
  • 26
    • 80051782401 scopus 로고    scopus 로고
    • Nickel chloride-catalyzed one-pot three-component synthesis of pyrazolophthalalzinyl spirooxindoles
    • Zhang, X.; Li, Y.; Zhang, Z. Nickel chloride-catalyzed one-pot three-component synthesis of pyrazolophthalalzinyl spirooxindoles. Tetrahedron 2011, 67, 7426-7430.
    • (2011) Tetrahedron , vol.67 , pp. 7426-7430
    • Zhang, X.1    Li, Y.2    Zhang, Z.3
  • 27
    • 79751536505 scopus 로고    scopus 로고
    • A novel and environment-friendly method for preparing dihydropyrano[2,3-c]pyrazoles in water under ultrasound irradiation
    • Zou, Y.; Wu, H.; Hu, Y.; Liu, H.; Zhao, X.; Ji, H.L.; Shi, D.Q. A novel and environment-friendly method for preparing dihydropyrano[2,3-c]pyrazoles in water under ultrasound irradiation. Ultrason. Sonochem. 2011, 18, 708-712.
    • (2011) Ultrason. Sonochem , vol.18 , pp. 708-712
    • Zou, Y.1    Wu, H.2    Hu, Y.3    Liu, H.4    Zhao, X.5    Ji, H.L.6    Shi, D.Q.7
  • 28
    • 0037404613 scopus 로고    scopus 로고
    • An efficient synthesis of 3,4-dihydropyrimidin-2-ones catalyzed by NH2SO3H under ultrasound irradiation
    • Li, J.T.; Han, J.F.; Yang, J.H.; Li, T.S. An efficient synthesis of 3,4-dihydropyrimidin-2-ones catalyzed by NH2SO3H under ultrasound irradiation. Ultrason. Sonochem. 2003, 10, 199-122.
    • (2003) Ultrason. Sonochem , vol.10 , pp. 199-122
    • Li, J.T.1    Han, J.F.2    Yang, J.H.3    Li, T.S.4
  • 29
    • 0032578889 scopus 로고    scopus 로고
    • The ultrasound promoted Knoevenagel condensation of aromatic aldehydes
    • PII S0040403998017894
    • McNulty, J.; Steere, J.A.; Wolf, S. The Ultrasound Promoted Knoevenagel Condensation of Aromatic Aldehydes. Tetrahedron Lett. 1998, 39, 8013-8016. (Pubitemid 28522252)
    • (1998) Tetrahedron Letters , vol.39 , Issue.44 , pp. 8013-8016
    • McNulty, J.1    Steere, J.A.2    Wolf, S.3
  • 30
    • 0000297349 scopus 로고
    • Enhancement of an Ullmann coupling reaction induced by ultrasound
    • Lindley, J.; Lorimer, J.P.; Mason, T.J. Enhancement of an Ullmann coupling reaction induced by ultrasound. Ultrasonics 1986, 24, 292-293.
    • (1986) Ultrasonics , vol.24 , pp. 292-293
    • Lindley, J.1    Lorimer, J.P.2    Mason, T.J.3
  • 31
    • 0032684321 scopus 로고    scopus 로고
    • Effects of intense ultrasound treatment of C-60 solutions
    • Heymann, D.; Cataldo, F. Effects of intense ultrasound treatment of C-60 solutions. Fullerene Sci. Technol. 1999, 7, 725-732.
    • (1999) Fullerene Sci. Technol , vol.7 , pp. 725-732
    • Heymann, D.1    Cataldo, F.2
  • 32
    • 0036296302 scopus 로고    scopus 로고
    • Synthesis of ethyl α-cyanocinnamates catalyzed by KF-Al2O3 under ultrasound irradiation
    • Wang, S.X.; Li, J.T.; Yang, W.Z.; Li, T.S. Synthesis of ethyl α-cyanocinnamates catalyzed by KF-Al2O3 under ultrasound irradiation. Ultrason. Sonochem. 2002, 9, 159-161.
    • (2002) Ultrason. Sonochem , vol.9 , pp. 159-161
    • Wang, S.X.1    Li, J.T.2    Yang, W.Z.3    Li, T.S.4
  • 33
    • 0007066464 scopus 로고    scopus 로고
    • Green chemistry. The sonochemical approach
    • Cintas, P.; Luche, J.L. Green chemistry. The sonochemical approach. Green Chem. 1999, 1, 115-125.
    • (1999) Green Chem , vol.1 , pp. 115-125
    • Cintas, P.1    Luche, J.L.2
  • 35
    • 33645222276 scopus 로고    scopus 로고
    • Power ultrasound in organic synthesis: Moving cavitational chemistry from academia to innovative and large-scale applications
    • DOI 10.1039/b503848k
    • Cravotto, G.; Cintas, P. Power ultrasound in organic synthesis: Moving cavitational chemistry from academia to innovative and large-scale applications. Chem. Soc. Rev. 2006, 35, 180-196. (Pubitemid 43485008)
    • (2006) Chemical Society Reviews , vol.35 , Issue.2 , pp. 180-196
    • Cravotto, G.1    Cintas, P.2
  • 36
    • 5644231162 scopus 로고    scopus 로고
    • Ultrasound-promoted alkynylation of ethynylbenzene to ketones under solvent-free condition
    • Ji, S.J.; Shen, Z.L.; Gu, D.G.; Huang, X.Y. Ultrasound-promoted alkynylation of ethynylbenzene to ketones under solvent-free condition. Ultrason. Sonochem. 2005, 12, 161-163.
    • (2005) Ultrason. Sonochem , vol.12 , pp. 161-163
    • Ji, S.J.1    Shen, Z.L.2    Gu, D.G.3    Huang, X.Y.4
  • 37
    • 70249121745 scopus 로고    scopus 로고
    • A convenient and efficient protocol for the synthesis of 5-aryl- 1,3-diphenylpyrazole catalyzed by hydrochloric acid under ultrasound irradiation
    • Li, J.T.; Yin, Y.; Li, L.; Sun, M.X. A convenient and efficient protocol for the synthesis of 5-aryl- 1,3-diphenylpyrazole catalyzed by hydrochloric acid under ultrasound irradiation. Ultrason. Sonochem. 2010, 17, 11-13.
    • (2010) Ultrason. Sonochem , vol.17 , pp. 11-13
    • Li, J.T.1    Yin, Y.2    Li, L.3    Sun, M.X.4
  • 39
    • 33847294239 scopus 로고    scopus 로고
    • Sonochemistry and the environment - Providing a "green" link between chemistry, physics and engineering
    • DOI 10.1016/j.ultsonch.2006.10.008, PII S1350417706001568
    • Mason, T.J. Sonochemistry and the environment-Providing a "green" link between chemistry, physics and engineering. Ultrason. Sonochem. 2007, 14, 476-483. (Pubitemid 46330095)
    • (2007) Ultrasonics Sonochemistry , vol.14 , Issue.4 , pp. 476-483
    • Mason, T.J.1
  • 41
    • 10044253193 scopus 로고    scopus 로고
    • An expeditious synthesis of β-indolylketones catalyzed by p-toluenesulfonic acid (PTSA) using ultrasonic irradiation
    • Ji, S.J.; Wang, S.Y. An expeditious synthesis of β-indolylketones catalyzed by p-toluenesulfonic acid (PTSA) using ultrasonic irradiation. Ultrason. Sonochem. 2005, 12, 339-343.
    • (2005) Ultrason. Sonochem , vol.12 , pp. 339-343
    • Ji, S.J.1    Wang, S.Y.2
  • 42
    • 25844521106 scopus 로고    scopus 로고
    • A novel base-promoted synthesis of β-indolylketones via a three-component condensation under ultrasonic irradiation
    • Shen, Z.L.; Ji, S.J.; Wang, S.Y.; Zeng, X.F. A novel base-promoted synthesis of β-indolylketones via a three-component condensation under ultrasonic irradiation. Tetrahedron 2005, 61, 10552-10558.
    • (2005) Tetrahedron , vol.61 , pp. 10552-10558
    • Shen, Z.L.1    Ji, S.J.2    Wang, S.Y.3    Zeng, X.F.4
  • 43
    • 34548271380 scopus 로고    scopus 로고
    • Hungerbühler, K. What is a green solvent? A comprehensive framework for the environmental assessment of solvents
    • Capello, C.; Fischer, U.; Hungerbühler, K. What is a green solvent? A comprehensive framework for the environmental assessment of solvents. Green Chem. 2007, 9, 927-934.
    • (2007) Green Chem , vol.9 , pp. 927-934
    • Capello, C.1    Fischer, U.2
  • 44
    • 5644262484 scopus 로고
    • The temperature of cavitation
    • Flint, E.B.; Suslick, K.S. The temperature of cavitation. Science 1991, 253, 1397-1399. (Pubitemid 21917288)
    • (1991) Science , vol.253 , Issue.5026 , pp. 1397-1399
    • Flint, E.B.1    Suslick, K.S.2
  • 46
    • 0025485944 scopus 로고
    • On the origin of sonoluminescene and sonochemistry
    • Suslick, K.S.; Doktycz, S.J.; Flint, E.B. On the Origin of Sonoluminescene and Sonochemistry. Ultrasonics 1990, 28, 280-282.
    • (1990) Ultrasonics , vol.28 , pp. 280-282
    • Suslick, K.S.1    Doktycz, S.J.2    Flint, E.B.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.