Potassium Carbonate–Mediated Efficient and Convenient Synthesis of 3-Methyl-1-phenylchromeno[4,3-c]pyrazol-4(1H)-ones

REFERENCES

• Selvam , C. ; Jachak , S. M. ; Thilagavathi , R. ; Chakraborti , A. K. Design, synthesis, biological evaluation, and molecular docking of curcumin analogues as antioxidant, cyclooxygenase inhibitory, and anti-inflammatory agents . Bioorg. Med. Chem. Lett. 2005 , 15 , 1793 – 1797 .
   PubMed Web of Science ®Google Scholar
• Khode , S. ; Maddi , V. ; Aragade , P. ; Palkar , M. ; Ronad , P. K. ; Mamledesai , S. ; Thippeswamy , A. H. M. ; Satyanarayana , D. Synthesis and pharmacological evaluation of a novel series of 5-(substituted) aryl-3-(3-coumarinyl)-1-phenyl-2-pyrazolines as novel anti-inflammatory and analgesic agents . Eur. J. Med. Chem. 2009 , 44 , 1682 – 1688 .
   PubMed Web of Science ®Google Scholar
• Goodell , J. R. ; Puig-Basagoiti , F. ; Forshey , B. M. ; Shi , P.-Y. ; Ferguson , D. M. Identification of compounds with anti–West Nile virus activity . J. Med. Chem. 2006 , 49 , 2127 – 2137 .
   PubMed Web of Science ®Google Scholar
• Ouyang , G. ; Cai , X.-J. ; Chen , Z. ; Song , B.-A. ; Bhadury , P. S. ; Yang , S. ; Jin , L.-H. ; Xue , W. ; Hu , D.-Y. ; Zeng , S. Synthesis and antiviral activities of pyrazole derivatives containing an oxime moiety. J. Agric. Food Chem. 2008, 56, 10160–10167.
   PubMed Web of Science ®Google Scholar
• Stein , R. G. ; Biel , J. H. ; Singh , T. Antimalarials: 4-Substituted 1H-pyrazolo [3,4-b] quinolines . J. Med. Chem. 1970 , 13 , 153 – 155 .
   PubMed Web of Science ®Google Scholar
• Mishra , S. ; Karmodiya , K. ; Surolia , N. ; Surolia , A. Synthesis and exploration of novel curcumin analogues as anti-malarial agents . Bioorg. Med. Chem. Lett. 2008 , 16 , 2894 – 2902 .
   Web of Science ®Google Scholar
• Sweeney , Z. K. ; Harris , S. F. ; Arora , N. ; Javanbakht , H. ; Li , Y. ; Fretland , J. ; Davidson , J. P. ; Billedeau , J. R. ; Gleason , S. K. ; Hirschfeld , D. Design of annulated pyrazoles as inhibitors of HIV-1 reverse transcriptase II . J. Med. Chem. 2008 , 51 , 7449 – 7458 .
   PubMed Web of Science ®Google Scholar
• Lynch , C. L. ; Hale , J. J. ; Budhu , R. J. ; Gentry , A. L. ; Finke , P. E. ; Caldwell , C. G. ; Mills , S. G. ; MacCoss , M. ; Shen , D.-M. ; Chapman , K. T. CCR5 antagonists: 3-(Pyrrolidin-1-yl) propionic acid analogues with potent anti-HIV activity . Org. Lett. 2003 , 5 , 2473 – 2475 .
   PubMed Web of Science ®Google Scholar
• Tanitame , A. ; Oyamada , Y. ; Ofuji , K. ; Fujimoto , M. ; Iwai , N. ; Hiyama , Y. ; Suzuki , K. ; Ito , H. ; Terauchi , H. ; Kawasaki , M. Synthesis and antibacterial activity of a novel series of potent DNA gyrase inhibitors: Pyrazole derivatives . J. Med. Chem. 2004 , 47 , 3693 – 3696 .
   PubMed Web of Science ®Google Scholar
• Holla , B. S. ; Mahalinga , M. ; Karthikeyan , M. S. ; Akberali , P. M. ; Shetty , N. S. Synthesis of some novel pyrazolo[3,4-d]pyrimidine derivatives as potential antimicrobial agents . Bioorg. Med. Chem. Lett. 2006 , 14 , 2040 – 2047 .
   Web of Science ®Google Scholar
• Baraldi , P. G. ; Balboni , G. ; Pavani , M. G. ; Spalluto , G. ; Tabrizi , M. A. ; Clercq , E. D. ; Balzarini , J. ; Bando , T. ; Sugiyama , H. ; Romagnoli , R. Design, synthesis, DNA binding, and biological evaluation of water-soluble hybrid molecules containing two pyrazole analogues of the alkylating cyclopropylpyrroloindole (CPI) subunit of the antitumor agent CC-1065 and polypyrrole minor groove binders . J. Med. Chem. 2001 , 44 , 2536 – 2543 .
   PubMed Web of Science ®Google Scholar
• Lin , R. ; Chiu , G. ; Yu , Y. ; Connolly , P. J. ; Li , S. ; Lu , Y. ; Adams , M. ; Fuentes-Pesquera , A. R. ; Emanuel , S. L. ; Greenberger , L. M. Design, synthesis, and evaluation of 3,4-disubstituted pyrazole analogues as anti-tumor CDK inhibitors . Bioorg. Med. Chem. Lett. 2007 , 17 , 4557 – 4561 .
   PubMed Web of Science ®Google Scholar
• Colotta , V. ; Cecchi , L. ; Filacchioni , G. ; Melani , F. ; Palazzino , G. ; Martini , C. ; Giannaccini , G. ; Lucacchini , A. Synthesis, binding studies, and structure–activity relationships of 1-aryl-and 2-aryl [1] benzopyranopyrazol-4-ones, central benzodiazepine receptor ligands . J. Med. Chem. 1988 , 31 , 1 – 3 .
   PubMed Web of Science ®Google Scholar
• Kidwai , M. ; Singhal , K. ; Rastogi , S. A convenient K2CO3-catalysed regioselective synthesis for benzopyrano[4,3-c]pyrazoles in aqueous medium . Heterocycles 2007 , 71 , 569 – 576 .
   Web of Science ®Google Scholar
• Colotta , V. ; Cecchi , L. ; Melani , F. ; Palazzino , G. ; Filacchioni , G. The correct synthesis of 2,3-dihydro-2-aryl-4-r-[1] benzopyrano [4, 3-c] pyrazole-3-ones . Tetrahedron Lett. 1987 , 28 , 5165 – 5168 .
   Web of Science ®Google Scholar
• Chantegrel , B. ; Nodi , A.-I. ; Gelin , S. 4-Oxo-1H-and-2H-[1]benzopyrano[4,3-c]pyrazoles: Preparation from 4-hydroxycoumarin or 3-chromonecarboxylic acid derivatives . Tetrahedron Lett. 1983 , 24 , 381 – 384 .
   Web of Science ®Google Scholar
• Stadlbauer , W. ; Hojas , G. Ring closure reactions of 3-arylhydrazonoalkyl-quinolin-2-ones to 1-aryl-pyrazolo [4, 3-c] quinolin-2-ones . J. Heterocycl. Chem. 2004 , 41 , 681 – 690 .
   Web of Science ®Google Scholar
• Manvar , A. ; Bochiya , P. ; Virsodia , V. ; Khunt , R. ; Shah , A. Microwave-assisted and Zn[l-proline]2-catalyzed tandem cyclization under solvent-free conditions: Rapid synthesis of chromeno[4,3-c]pyrazol-4-ones . J. Mol. Catal. A: Chem. 2007 , 275 , 148 – 152 .
   Web of Science ®Google Scholar
• Padilla-Martinez , I. I. ; Flores-Larios , I. Y. ; GarcÃa-Baez , E. V. ; Gonzalez , J. ; Cruz , A. ; MartÃnez-Martinez , F. J. X-ray supramolecular structure, NMR spectroscopy, and synthesis of 3-methyl-1-phenyl-1-H-chromeno[4,3-c]pyrazol-4-ones formed by the unexpected cyclization of 3-[1-(phenyl-hydrazono)ethyl]-chromen-2-ones. Molecules 2011, 16, 915–932.
   PubMed Web of Science ®Google Scholar
• Yang , G.-Y. ; Yang , J.-T. ; Wang , C.-X. ; Fan , S.-F. ; Xie , P.-H. ; Xu , C.-L. Microwave-assisted synthesis of 3-methyl-1-phenylchromeno[4,3-c]pyrazol-4(1 h)-ones under solvent-free conditions . Heterocycles 2013 , 87 , 1337–1347 .
   Web of Science ®Google Scholar
• Yang , G.-Y. ; Wang , C.-X. ; Fan , S.-F. ; Zhao , L.-J. ; Wang , D. ; Xu , C.-L. Study on the cyclization methods of 3-[1-(phenyl-hydrazono) ethyl] ethyl]-chromen-2-ones . Synth. Commun. 2013 , 43 , 1263 – 1269 .
   Web of Science ®Google Scholar
• Al-Ayed , A. S. Synthesis of new substituted chromen [4, 3-c] pyrazol-4-ones and their antioxidant activities . Molecules 2011 , 16 , 10292 – 10302 .
   PubMed Web of Science ®Google Scholar
• Kidwai , M. ; Lal , M. ; Mishra , N. K. ; Jahan , A. Potassium carbonate as a green catalyst for Markovnikov addition of azoles to vinyl acetate in PEG . Green Chem. Lett. Rev. 2013 , 6 , 63 – 68 .
   Web of Science ®Google Scholar
• Kidwai , M. ; Bhatnagar , D. ; Chauhana , R. Potassium carbonate–mediated green and efficient synthesis of imidazo[2,1-b]-1,3,4-thiadiazoles using PEG as solvent . J. Heterocycl. Chem. 2013 , 50 , E234 – E236 .
   Web of Science ®Google Scholar
• ICH Guideline Q3C (R5) on Impurities: Guideline for Residual Solvents; Geneva: International Conference on Harmonization , 2005 .
   Google Scholar
• Ma , S. ; Wu , L. ; Liu , M. ; Xu , X. ; Huang , Y. ; Yang , Y. Highly enantioselective aza-Michael addition reactions of 4-nitrophthalimide with α,β-unsaturated ketones . RSC Adv. 2013 , 3 , 11498 – 11501 .
   Web of Science ®Google Scholar
• Brehme , R. ; Enders , D. ; Fernandez , R. ; Lassaletta , J. M. Aldehyde n,n-dialkylhydrazones as neutral acyl anion equivalents: Umpolung of the imine reactivity . Eur. J. Org. Chem. 2007 , 5629 – 5660 .
   Web of Science ®Google Scholar
• Shawali , A. S. ; Parkanyi , C. Hydrazidoyl halides in the synthesis of heterocycles . J. Heterocycl. Chem. 1980 , 17 , 833 – 854 .
   Web of Science ®Google Scholar
• Color versions of one or more of the figures in the article can be found online at www.tandfonline.com/lsyc.
   Google Scholar