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Volumn 44, Issue 11, 2014, Pages 1635-1640

Synthesis of 3-(3-methyl-1-aryl-1H-pyrazol-5-yl)-2H-2-chromen-2-one derivatives via a one-pot, three-component reaction

Author keywords

4 hydroxy 6 methyl 2H pyran 2 one; Arylhydrazine; coumarin; pyrazole; salicylaldehyde

Indexed keywords

3 (3 METHYL 1 PHENYL 1H PYRAZOL 5 YL) 2H CHROMEN 2 ONE; ACETONITRILE; CHROMENE DERIVATIVE; COUMARIN DERIVATIVE; PIPERIDINE; PYRAZOLE DERIVATIVE; SALICYLALDEHYDE; UNCLASSIFIED DRUG;

EID: 84901373504     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2013.867507     Document Type: Article
Times cited : (10)

References (29)
  • 1
    • 38949175741 scopus 로고    scopus 로고
    • Synthesis and antifungal activity of some new 3-hydroxy-2-(1-phenyl-3- aryl-4-pyrazolyl)chromones
    • Prakash, O.; Kumar, R.; Parkash, V. Synthesis and antifungal activity of some new 3-hydroxy-2-(1-phenyl-3-aryl-4-pyrazolyl)chromones. Eur. J. Med. Chem. 2008, 43, 435.
    • (2008) Eur. J. Med. Chem. , vol.43 , pp. 435
    • Prakash, O.1    Kumar, R.2    Parkash, V.3
  • 2
    • 0034624679 scopus 로고    scopus 로고
    • Novel 1,5-diphenylpyrazole nonnucleoside HIV-1 reverse transcriptase inhibitors with enhanced activity versus the delavirdine-resistant P236L mutant: Lead identification and SAR of 3- and 4-substituted derivatives
    • Genin, M. J.; Biles, C.; Keiser, B. J.; Poppe, S. M.; Swaney, S. M.; Tarpley, W. G.; Yagi, Y.; Romero, D. L. Novel 1,5-diphenylpyrazole nonnucleoside HIV-1 reverse transcriptase inhibitors with enhanced activity versus the delavirdine-resistant P236L mutant: Lead identification and SAR of 3- and 4-substituted derivatives. J. Med. Chem. 2000, 43, 1034.
    • (2000) J. Med. Chem. , vol.43 , pp. 1034
    • Genin, M.J.1    Biles, C.2    Keiser, B.J.3    Poppe, S.M.4    Swaney, S.M.5    Tarpley, W.G.6    Yagi, Y.7    Romero, D.L.8
  • 4
    • 34548501268 scopus 로고    scopus 로고
    • CYP2C9 Structure-metabolism relationships: Optimizing the metabolic stability of COX-2 inhibitors
    • Ahlstrom, M. M.; Ridderstrom, M.; Zamora, I.; Luthman, K. CYP2C9 Structure-metabolism relationships: Optimizing the metabolic stability of COX-2 inhibitors. J. Med. Chem. 2007, 50, 4444.
    • (2007) J. Med. Chem. , vol.50 , pp. 4444
    • Ahlstrom, M.M.1    Ridderstrom, M.2    Zamora, I.3    Luthman, K.4
  • 5
    • 0003607021 scopus 로고    scopus 로고
    • A.R. Katritzky, C.W. Rees, E.F.V. Scriven (Eds.); Pergamon: Oxford
    • Elguero, J. In Comprehensive Heterocyclic Chemistry; A. R. Katritzky, C. W. Rees, E. F. V. Scriven (Eds.); Pergamon: Oxford, 1996; Vol. 5.
    • (1996) Comprehensive Heterocyclic Chemistry , vol.5
    • Elguero, J.1
  • 7
    • 50449095093 scopus 로고    scopus 로고
    • Syntheses and phosphorescent properties of blue emissive iridium complexes with tridentate pyrazolyl ligands
    • Yang, L.; Okuda, F.; Kobayashi, K.; Nozaki, K.; Tanabe, Y.; Ishii, Y.; Haga, M. Syntheses and phosphorescent properties of blue emissive iridium complexes with tridentate pyrazolyl ligands. Inorg. Chem. 2008, 47, 7154.
    • (2008) Inorg. Chem. , vol.47 , pp. 7154
    • Yang, L.1    Okuda, F.2    Kobayashi, K.3    Nozaki, K.4    Tanabe, Y.5    Ishii, Y.6    Haga, M.7
  • 8
    • 38149100485 scopus 로고    scopus 로고
    • Blue-emitting platinum(II) complexes bearing both pyridylpyrazolate chelate and bridging pyrazolate ligands: Synthesis, structures, and photophysical properties
    • Chang, S. Y.; Chen, J. L.; Chi, Y. Blue-emitting platinum(II) complexes bearing both pyridylpyrazolate chelate and bridging pyrazolate ligands: Synthesis, structures, and photophysical properties. Inorg. Chem. 2007, 46, 11202.
    • (2007) Inorg. Chem. , vol.46 , pp. 11202
    • Chang, S.Y.1    Chen, J.L.2    Chi, Y.3
  • 9
    • 35048883559 scopus 로고    scopus 로고
    • Tetrahedral zinc complexes with liquid crystalline and luminescent properties: Interplay between nonconventional molecular shapes and supramolecular mesomorphic order
    • Cavero, E.; Uriel, S.; Romero, P.; Serrano, J. L.; Giménez, R. Tetrahedral zinc complexes with liquid crystalline and luminescent properties: Interplay between nonconventional molecular shapes and supramolecular mesomorphic order. J. Am. Chem. Soc. 2007, 129, 11608.
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 11608
    • Cavero, E.1    Uriel, S.2    Romero, P.3    Serrano, J.L.4    Giménez, R.5
  • 10
    • 34848859255 scopus 로고    scopus 로고
    • Synthesis of pentafluorosulfanylpyrazole and pentafluorosulfanyl-1,2,3- triazole and their derivatives as energetic materials by click chemistry
    • Ye, C.; Gard, G. L.; Winter, R. W.; Syvret, R. G.; Twamley, B.; Shreeve, J. M. Synthesis of pentafluorosulfanylpyrazole and pentafluorosulfanyl-1,2,3- triazole and their derivatives as energetic materials by click chemistry. Org. Lett. 2007, 9, 3841.
    • (2007) Org. Lett. , vol.9 , pp. 3841
    • Ye, C.1    Gard, G.L.2    Winter, R.W.3    Syvret, R.G.4    Twamley, B.5    Shreeve, J.M.6
  • 11
    • 80755168455 scopus 로고    scopus 로고
    • From 2000 to mid-2010: A fruitful decade for the synthesis of pyrazoles
    • Fustero, S.; Sánchez-Roselló, M.; Barrio, P.; Simón-Fuentes, A. From 2000 to mid-2010: A fruitful decade for the synthesis of pyrazoles. Chem. Rev. 2011, 111, 6984.
    • (2011) Chem. Rev. , vol.111 , pp. 6984
    • Fustero, S.1    Sánchez-Roselló, M.2    Barrio, P.3    Simón-Fuentes, A.4
  • 12
    • 84879307555 scopus 로고    scopus 로고
    • Route to pyrazolo[5,1-A]isoquinolines via a copper-catalyzed tandem reaction of 2-alkynylbromobenzene with pyrazole
    • Pan, X.; Luo, Y.; Wu, J. Route to pyrazolo[5,1-a]isoquinolines via a copper-catalyzed tandem reaction of 2-alkynylbromobenzene with pyrazole. J. Org. Chem. 2013, 78, 5756.
    • (2013) J. Org. Chem. , vol.78 , pp. 5756
    • Pan, X.1    Luo, Y.2    Wu, J.3
  • 13
    • 84868239360 scopus 로고    scopus 로고
    • Efficient multicomponent strategy to pentacyclic pyrazole-fused naphtho[1,8-fg]isoquinolines through cleavage of two carbon-carbon bonds
    • Hao, W. J.; Xu, X. P.; Bai, H-W.; Wang, S. Y.; Ji, S. J. Efficient multicomponent strategy to pentacyclic pyrazole-fused naphtho[1,8-fg] isoquinolines through cleavage of two carbon-carbon bonds. Org. Lett. 2012, 14, 4894.
    • (2012) Org. Lett. , vol.14 , pp. 4894
    • Hao, W.J.1    Xu, X.P.2    Bai, H.-W.3    Wang, S.Y.4    Ji, S.J.5
  • 15
    • 84929297636 scopus 로고    scopus 로고
    • Synthesis of some tetrazole fused pyrido[2,3-c] coumarin derivatives from a one-pot three-component reaction via intramolecular 1,3-dipolar cycloaddition reaction of azide to nitriles
    • Borah, P.; Naidu, P. S.; Bhuyan, P. J. Synthesis of some tetrazole fused pyrido[2,3-c] coumarin derivatives from a one-pot three-component reaction via intramolecular 1,3-dipolar cycloaddition reaction of azide to nitriles. Tetrahedron Lett. 2012, 53, 5034.
    • (2012) Tetrahedron Lett. , vol.53 , pp. 5034
    • Borah, P.1    Naidu, P.S.2    Bhuyan, P.J.3
  • 16
    • 0036756189 scopus 로고    scopus 로고
    • Structure-activity relationships of some 3-substituted-4-hydroxycoumarins as HIV-1 protease inhibitors
    • Kirkiacharian, S.; Thuy, D. T.; Sicsic, S.; Bakhchinian, R.; Kurkjian, R.; Tonnaire, T. Structure-activity relationships of some 3-substituted-4- hydroxycoumarins as HIV-1 protease inhibitors. Farmaco 2002, 57, 703.
    • (2002) Farmaco , vol.57 , pp. 703
    • Kirkiacharian, S.1    Thuy, D.T.2    Sicsic, S.3    Bakhchinian, R.4    Kurkjian, R.5    Tonnaire, T.6
  • 17
    • 77949567018 scopus 로고    scopus 로고
    • Catalyst-free regioselective synthesis of benzopyran-annulated thiopyrano[2,3-b]thiochromen-5-(4H)-one derivatives by domino-Knoevenagel- hetero-Diels-Alder reaction of terminal alkynes with 4-hydroxy dithiocoumarin in aqueous medium
    • Majumdar, K. C.; Taher, A.; Ponra, P. Catalyst-free regioselective synthesis of benzopyran-annulated thiopyrano[2,3-b]thiochromen-5-(4H)-one derivatives by domino-Knoevenagel-hetero-Diels-Alder reaction of terminal alkynes with 4-hydroxy dithiocoumarin in aqueous medium. Tetrahedron Lett. 2010, 51, 2297.
    • (2010) Tetrahedron Lett. , vol.51 , pp. 2297
    • Majumdar, K.C.1    Taher, A.2    Ponra, P.3
  • 18
    • 26444461246 scopus 로고    scopus 로고
    • Synthesis and antiinflammatory activity of coumarin derivatives
    • Kontogiorgis, C. A.; Hadjipavlou-Litina, D. J. Synthesis and antiinflammatory activity of coumarin derivatives. J. Med. Chem. 2005, 48, 6400.
    • (2005) J. Med. Chem. , vol.48 , pp. 6400
    • Kontogiorgis, C.A.1    Hadjipavlou-Litina, D.J.2
  • 19
    • 33846338767 scopus 로고    scopus 로고
    • A rapid access to indolo [2,1-A]pyrrolo[4′,3′:4,5]pyrano[5,6- c]coumarin/[6,5-c]chromone derivatives by domino Knoevenagal intramolecular hetero-Diels-Alder reactions
    • Durga, R.; Manian, R. S.; Jayashankaran, J.; Raghunathan, R. A rapid access to indolo [2,1-a]pyrrolo[4′,3′:4,5]pyrano[5,6-c]coumarin/[6, 5-c]chromone derivatives by domino Knoevenagal intramolecular hetero-Diels-Alder reactions. Tetrahedron Lett. 2007, 48, 1385.
    • (2007) Tetrahedron Lett. , vol.48 , pp. 1385
    • Durga, R.1    Manian, R.S.2    Jayashankaran, J.3    Raghunathan, R.4
  • 20
    • 84872103971 scopus 로고    scopus 로고
    • Greener protocol for one pot synthesis of coumarin styryl dyes
    • Phadtare, S. B.; Jarag, K. J.; Shankarling, G. S. Greener protocol for one pot synthesis of coumarin styryl dyes. Dyes Pigm. 2013, 97, 105.
    • (2013) Dyes Pigm. , vol.97 , pp. 105
    • Phadtare, S.B.1    Jarag, K.J.2    Shankarling, G.S.3
  • 23
    • 84870943115 scopus 로고    scopus 로고
    • Design, synthesis, and biological evaluation of coumarin alkylamines as potent and selective dual binding site inhibitors of acetylcholinesterase
    • Catto, M.; Pisani, L.; Leonetti, F.; Nicolotti, O.; Pesce, P.; Stefanachi, A.; Cellamare, S.; Carotti, A. Design, synthesis, and biological evaluation of coumarin alkylamines as potent and selective dual binding site inhibitors of acetylcholinesterase. Bioorg. Med. Chem. 2013, 21, 146.
    • (2013) Bioorg. Med. Chem. , vol.21 , pp. 146
    • Catto, M.1    Pisani, L.2    Leonetti, F.3    Nicolotti, O.4    Pesce, P.5    Stefanachi, A.6    Cellamare, S.7    Carotti, A.8
  • 24
    • 84861967505 scopus 로고    scopus 로고
    • Nucleophilic properties of a nonstabilized azomethine ylide derived from sarcosine and cyclohexanone: A novel domino reaction leading to substituted 4-aryl-2-pyrrolidones
    • Moshkin, V. S.; Sosnovskikh, V. Y.; Roschenthaler, G.-V. Nucleophilic properties of a nonstabilized azomethine ylide derived from sarcosine and cyclohexanone: A novel domino reaction leading to substituted 4-aryl-2-pyrrolidones. Tetrahedron Lett. 2012, 53, 3568.
    • (2012) Tetrahedron Lett. , vol.53 , pp. 3568
    • Moshkin, V.S.1    Sosnovskikh, V.Y.2    Roschenthaler, G.-V.3
  • 25
    • 84867890112 scopus 로고    scopus 로고
    • A simple and expedient synthesis of functionalized pyrido[2,3-c] coumarin derivatives using molecular iodine catalyzed threecomponent reaction
    • Khan, A. T.; Das, D. K.; Islam, K.; Das, P. A simple and expedient synthesis of functionalized pyrido[2,3-c] coumarin derivatives using molecular iodine catalyzed threecomponent reaction. Tetrahedron Lett. 2012, 53, 6418.
    • (2012) Tetrahedron Lett. , vol.53 , pp. 6418
    • Khan, A.T.1    Das, D.K.2    Islam, K.3    Das, P.4
  • 26
    • 84860629113 scopus 로고    scopus 로고
    • Synthesis of heterocyclic[3.3.3]propellanes via a sequential four-component reaction
    • Alizadeh, A.; Rezvanian, A.; Zhu, L. G. Synthesis of heterocyclic[3.3.3] propellanes via a sequential four-component reaction. J. Org. Chem. 2012, 77, 4385.
    • (2012) J. Org. Chem. , vol.77 , pp. 4385
    • Alizadeh, A.1    Rezvanian, A.2    Zhu, L.G.3
  • 27
    • 84875269722 scopus 로고    scopus 로고
    • A novel and efficient synthesis of 3-[(4,5-dihydro-1Hpyrrol- 3-yl)carbonyl]-2H-chromen-2-ones (=3-[(4,5-dihydro-1H-pyrrol-3-yl)carbonyl]-2- H-1-benzopyran-2-ones)
    • Alizadeh, A.; Ghanbaripour, R. A novel and efficient synthesis of 3-[(4,5-dihydro-1Hpyrrol- 3-yl)carbonyl]-2H-chromen-2-ones (=3-[(4,5-dihydro-1H- pyrrol-3-yl)carbonyl]-2- H-1-benzopyran-2-ones). Helv. Chim. Acta 2013, 96, 473.
    • (2013) Helv. Chim. Acta , vol.96 , pp. 473
    • Alizadeh, A.1    Ghanbaripour, R.2
  • 28
    • 84883193825 scopus 로고    scopus 로고
    • An approach to the synthesis of 2-acylchromeno[3,4-c]pyrrol-4(2H)-one derivatives via a sequential three-component reaction
    • Alizadeh, A.; Ghanbaripour, R.; Zhu, L. G. An approach to the synthesis of 2-acylchromeno[3,4-c]pyrrol-4(2H)-one derivatives via a sequential three-component reaction. Synlett 2013, 24, 2124.
    • (2013) Synlett , vol.24 , pp. 2124
    • Alizadeh, A.1    Ghanbaripour, R.2    Zhu, L.G.3
  • 29
    • 80855132758 scopus 로고    scopus 로고
    • Envirocat EPZ-10: An efficient catalyst for the synthesis of 3-acetoacetylcoumarins
    • Shaikh, T. S.; Undale, K. A.; Gaikwad, D. S.; Pore, D. M. Envirocat EPZ-10: An efficient catalyst for the synthesis of 3-acetoacetylcoumarins. C. R. Chim. 2011, 14, 987.
    • (2011) C.R. Chim. , vol.14 , pp. 987
    • Shaikh, T.S.1    Undale, K.A.2    Gaikwad, D.S.3    Pore, D.M.4


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