The Preparation of 2-(1-Phenyl-5-Phenyl or 5-Substituted Phenyl-1H-Pyrazol-3-Yl)Phenols from Trilithiated 2′-Hydroxyacetophenone Phenylhydrazone and Aromatic Esters

References

• Elguero , J. 1984 . Comprehensive Heterocyclic Chemistry , Edited by: Potts , K. T. Vol. 5 , 167 – 343 . New York, New York : Pergamon Press . Part 4A (4.04)
   Google Scholar
• Fusco , R. 1967 . The Chemistry Of Heterocyclic Compounds , Edited by: Weissberger , A. 1 – 137 . New York, New York : Interscience Publishers .
   Google Scholar
• Jarboe , H. 1967 . The Chemistry of Heterocyclic Compounds , Edited by: Weissberger , A. 177 – 285 . New York, New York : Interscience Publishers .
   Google Scholar
• Kost , A. N. and Grandberg , I. 1966 . Advances in Heterocyclic Chemistry , 6 : 347
   Google Scholar
• Ahmad , R. , Khan , M. N. and Kausar , N. 1996 . Arabian J. Sci. Eng. , 21 : 393
   Google Scholar
• Baker , W. , Harborne , J. B. and Ollis , W. D. 1952 . J. Chem. SOC. , 1303
   Google Scholar
• Kallay , F. , Janzso , G. and Koczor , I. 1968 . Tetrahedron Lett , 3853
   Google Scholar
• Song , G. ‐Y. and Ahn , B. ‐Z. 1994 . Arch. Pharmacol. Res. , 17 : 434
   PubMedGoogle Scholar
• Ahmad , R. and Zia‐UI‐Haq , M. 1995 . Turk. J. Chem. , 19 : 101
   Google Scholar
• Murthy , M. , Sree , R. and Rao , E. V. 1985 . Indian Drugs , 22 : 462
   Google Scholar
• Murthy , M. , Sree , R. , Rao , E. V. and Ranganatham , P. 1985 . Indian Drugs , 22 : 247
   Google Scholar
• Joshi , M. G. and Wadokar , K. N. 1982 . Indian J Chem. Sect. B , 21B : 689
   Google Scholar
• Addison , A. W. and Burke , P. J. 1981 . J. Heterocycl. Chem. , 18 : 803
   Web of Science ®Google Scholar
• Udachi , Yu. M. , Charsinova , L. V. , Przheval'skii , N. M. , Grandger , I. I. and Tokmakov , G. P. 1980 . Izv. Timiryazeuk S‐kh. Akad , 162
   Google Scholar
• Ahamad , R. , Zai‐ul‐Haq , M. , Khan , N. and Kausar , N. 1996 . Arabian J. Sci. Eng. , 21 : 393
   Google Scholar
• Sharma , T. C. , Rojindae , B. D. D. and Kale , A. V. 1987 . Indian J. Chem., Sect. B , 26B : 687
   Google Scholar
• Sharma , T. C. , Pawar , S. R. and Reddy , N. J. 1983 . Acta Chim. Hung. , 112 : 159
   Google Scholar
• Ferlux . Fr. Demande . 2, 104,932 . 1972 . Chem. Abstr. 1972, 77, 164690. [M.p., not easily available]
   Google Scholar
• Cummings , R. T. , DiZio , J. P. and Krafft , G. A. 1988 . Tetrahedron Lett. , 29 : 69
   Web of Science ®Google Scholar
• Nagarathnam , D. and Cushman , M. 1991 . Tetrahedron , 47 : 5071
   Web of Science ®Google Scholar
• Nishinaga , A. H. , Maruyama , K. and Mashino , T. 1992 . Synth. , 839
   Google Scholar
• Cunningham , B. D. M. , Lowe , P. R. and Treadgill , M. D. 1989 . J. Chem. SOC., Perkin Trans II , 1275
   Google Scholar
• Bansal , V. , Singh , P. K. and Rhanna , R. N. 1996 . Indian J. Chem., Sect B, Org. Chem. Incl. Med. Chem. , 35B : 586
   Google Scholar
• Ahmad , R. , Malik , M. A. and Zia‐U1‐Haq , M. 1990 . J. Chem. SOC. Pak. , 12 : 352
   Google Scholar
• Wallet , J. ‐C. and Gaydou , E. M. 1996 . Synthetic Communications , 26 : 4097
   Web of Science ®Google Scholar
• Sarma , G. V. S. , Azam , M. A. and Sureshi , B. 1996 . Indian Drugs , 33 : 267
   Google Scholar
• Choshi , Horimoto S. , Wang , C. Y. , Magase , H. , Ichikawa , M. , Sugino , E. and Hibino , S. 1992 . Chem. Pharm. Bull. , 40 : 1047
   PubMed Web of Science ®Google Scholar
• Ishihara , H. and Hirahayashi , Y. 1978 . Chem. Lett. , 1007
   Google Scholar
• L'Abbe , G. and Mathys , G. 1974 . J. Heterocycl. Chem. , 11 : 613
   Google Scholar
• Mazat , C. L. , Beam , C. F. and Hines , M. A. 1990 . Synthetic Communications , 20 : 253
   Web of Science ®Google Scholar
• Citation name: 5H ‐Pyrazolo‐ [ 1,5‐c ][ 1,3]‐benzoxazin‐5‐ones
   Google Scholar
• Martinez , M. L. , Cooper , W. C. and Chou , P. T. 1992 . Phys. Lett. , 193 : 151
   Google Scholar
• Martinez , M. L. , Studer , S. L. and Chou , P. T. 1991 . J. Am. Chem. Soc. , 113 : 5881
   Google Scholar
• Sengupta , P. K. and Kasha , M. 1979 . Chem. Phys. Lett , 68 : 382
   Web of Science ®Google Scholar
• Itoh , M. and Fujiwara , Y. 1985 . J. Am. Chem. Soc. , 107 : 1561
   Google Scholar
• Mirone , P. and Vampiri , M. 1952 . Atti. Accd, Nml. Lincei., Rend. Classe Sci. Fis., Mate Nat. , 12 : 583 Chem. Abstr. 1952, 46, 9423
   Google Scholar
• Combustion analyses were performed by Quantitative Technologies, Inc., P. O. Box 470, Salem Industrial Park, Bldg. 5, Whitehouse, NJ 08888. Molecular formulas are in the Table: Compd. No., Anal. Calcd. 1 Found [% C, H, and/or N]: 1. C, 80.96180.69; H, 5.5615.70; N, 8.5818.22. 2. C, 74.18174.06; H, 5.4115.37; N, 7.5217.40. 3. C, 71.62171.59; H, 5.5115.54; N, 6.961 6.87. 4. C, 76.811 76.59; H,4.91/5.01;N, 8.5318.41. 5. C, 74.18174.31;H, 5.41/5.46;N, 7.521 7.49. 6. C, 81.49181.56; H, 6.5616.57;N, 7.6017.56. 7. N, 8.0817.94. 8. C, 76,81176.58; H, 4.9115.05; N, 8.5318.32. 9. C, 77.72177.63; H, 5.9516.05; N, 11.82111.68. 10. C,81.15/81.52;H, 5.9216.14; N,8.23/8.12. 11. N, 8.971 8.90. 12. C, 76.66176.39; H, 4.8214.80; N, 13.41113.23. 13. C, 76.66176.34; H, 4.8214.76; N, 13.411 13.27. 14. C, 81.98181.93; H, 4.8214.65;N, 9.561 9.38
   Google Scholar
• Fourier Transform infrared spectra were obtained on a Nicolet Impact 4 10 FT‐IR. Proton magnetic resonance spectra were obtained with a Varian Associates EM‐360L nuclear magnetic resonance spectrometer, and chemical shifts are recorded in δ ppm downfield from an internal tetramethylsilane standard. From Table: Compd. No., FT‐IR data (paraffin oil ‐ all compounds), 'H NMR data (varied solvents ‐ indicated). 1. H NMR (CDCl3) δ ppm 2.40 (s, 3H, ArCH,), 6.80 (s, IH, C,‐H) 7.67–8.67 (m, 13H, C,‐H and ArH) and 11.OO (s, 1H, ArOH, exch with D,O). 2. FT‐IR, 3 167 (OH) and 1584 (ArH) cm−1;1. H NMR (CDCl3) δ ppm 3.67 and 3.90 (s, 3H and 3H, ArOCH3), 6.73–7.83 (m, 13H, C4−H and Arm and 11.00 (s, lH, ArOH exch. with D2 O). 3. FT‐IR, 3167 (OH) and 1584 (ArH) cm−1;1. H NMR (CDCl3,) δ ppm 3.70 (s, 6H, ArOCH,), 3.93 (s, 3H, ArOCH3), 6.53 (s, 2H, ArH), 6.93 (s, 1H, C4−H) and 7.00 ‐7.80 (m, 9H, ArH), and 10.93 (s, 1H, ArOH, exch. with D2O). 4. FT‐IR, 3133–3381 (OH) cm−1;1. H NMR (DMSO‐d6) δ ppm 6.80–8.13 (m, 14H, C4−H and ArH) and 9.73–10.80 (broad, 2H, ArOH, exch. with D2O). 5. FT‐IR, 3 181 (OH) and 1591 (ArH) cm−1;1. H NMR (CDCl3) δ ppm, 3.70 (s, 6H, ArOCH3), 6.47 and 6.80–7.87 (s and m, 13H, C4−H and ArH) and 10.93 (s, 1H, ArOH exch. With D2O). 6. FT‐IR, 3181 (OH) and 1591 (Arm cm−1;1. H NMR(CDC13) δ ppm, 1.33 (s, 9H, ArC(CH3) 3)6.87–7.80 (m, 14H, C4−H and ArH) and 11.00 (s, 1H, ArOH exch. with D2O). 7. FT‐IR, 3 181 (OH) and 1618, 1605 and 1598 (several ArH) cm−1;1. H NMR (CDCl3) δ ppm 6.93 (s, 1H, C4−H), 7.67–8.10 (m, 13H. ArH) and 10.90 (s, 1H, ArOH, exch. with D2O). 8. FT‐IR, 3381,3167‐ 3188 (OH) and 1584 (ArH) cm−1;1. HNMR (DMSO‐d6, and CDC13) δ ppm, 6.87 (s, 1H, C4−H), 7.00–7.93 (m, 13H, ArH), 9.53 (s‐broad, lH, ArOH exch. with D,O) and 10.80 (s‐sharp, 1H, ArOH exch. with th D2O). 9. FT‐IR, 3174 (OH) and 1611 (ArH) cm−1; 1. H NMR (CDCl3) δ ppm, 2.98 (s, 6H, N(CH,)J, 6.77–7.90 (m, 14H, C,‐H and ArH) and 11.10 (s, 1H, ArOH exch. with D2O). 10. FT‐IR, 3181 (OH) and 1605 (ArH) cm−1; 1. H NMR (CDC13,) δ ppm, 2.27 (s, 6H, ArCH3), 6.90–7.83 (m, 13H, C4−H and ArH), and 11.07 (s, 1H, ArOH exch. with D2O). 11. FT‐TR, 3181 (OH) 1618 and 1584 (ArH) cm−1;1. H NMR (CDC13) δ ppm 6.90 (s, 1 9 C4−H) 7.07–7.80 (m. 14H, ArH) and 11.00 (s, 1H, ArOH exch. with D2O). 12. FT‐IR, 3153–3195 (OH), 1611, 1597, and 1591 (several ArH) cm−1;1. H NMR (CDCl3) δ ppm 7.00 (s, 1H, C4H), 7.07‐ 8.00 (m. 12H, ArH), 8.73 (s, 1H, ArH), and 10.83 (s, IH, ArOHexch. With D2 O). 13. FT‐IR, 3160–3188 (OH), 1611. 1598, 1591 (several ArH) cm−1; 1. H NMR (CDCl3) δ ppm 6.80–8.26 and 8.60 (m, 14H, C4−H and ArH), and 11.00 (s, 1H, ArOH exch. with D2O). 14. FT‐IR, 3174–3188 (OH) and 1618, 1584 with shoulder (several ArH) cm−1;1. H NMR (CDCl3) δ ppm 7.10 (s, 1H, C4−H), 7.20–8.60 (m, 19H, ArH), and 10.97 (s, 1H, ArOH exch. with D2O)
   Google Scholar
• Duncan , D. C. , Trumbo , T. A. , Almquist , C. D. , Lentz , T. A. and Beam , C. F. 1987 . J. Heterocycl. Chem. , 24 : 555
   Web of Science ®Google Scholar
• Angel , A. J. , Hurst , D. R. , Williams , A. R. , French , K. L. and Beam , C. F. 1998 . Synthetic Communications
   Google Scholar
• UV spectra were obtained with a Perkin Elmer Lambda 6 UV/VIS Spectrometer. Emission spectra were obtained on a Perkin‐Elmer LS 50B Luminescence Spectrometer
   Google Scholar
• Siebrand , W. and Williams , D. F. 1968 . J. Chem. Phys. , 49 : 1860
   Web of Science ®Google Scholar
• ortfzo‐Hydroxyphenylpyrazoles 2–4, and 9 have electron donating groups such as methoxy, hydroxy, or dimethylamino in the 4‐position of the pendant 5‐substituent, and they are capable of increasing the electron density of the pyrazole ring. By contrast, compounds 13 and 14 have electron withdrawing heterocyclic nitrogen atoms in the 4‐position of the pendant‐5 substituent
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