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Abstract
Several 1-substituted-3-aryl-1H-pyrazole-4-carbaldehyde (3a-g) derivatives were synthesized by substituted acetophenone (1a-d), substituted hydrazine (2a-b) and DMF in POCl3 and reaction mixture was irradiated with microwave at 20% power to furnish 1-substituted-3-aryl-1H-pyrazole-4-carbaldehydes derivatives (3a-g).
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References
- N.E. Santos, A.R.F. Carreira, V.L.M. Silva and S.S. Braga, Natural and Biomimetic Antitumor Pyrazoles, A Perspective, Molecules, 25, 1364 (2020); https://doi.org/10.3390/molecules25061364
- A. Olyaei and M. Sadeghpour, Recent Developments in the Synthesis and Applications of Furopyrazoles, New J. Chem., 44, 14791 (2020); https://doi.org/10.1039/D0NJ02178D
- N. Sugimoto, H. Watanabe and A. Ide, The Synthesis of L-a-Amino-b-(pyrazolyl-N)propionic Acid in Citrullus vulgaris, Tetrahedron, 11, 231 (1960); https://doi.org/10.1016/S0040-4020(01)93171-0
- J.G. Buchanan, A. Stobie and R.H. Wightman, C-Nucleoside Studies. Part 14. A New Synthesis of Pyrazofurin, J. Chem. Soc., Perkin Trans., 2374 (1981); https://doi.org/10.1039/p19810002374
- A. Morimoto, K. Noda, T. Watanabe and H. Takasugi, The Total Synthesis of Withasomnine, A Unique Pyrazole Alkaloid, Tetrahedron Lett., 9, 5707 (1968); https://doi.org/10.1016/S0040-4039(00)70757-X
- K.R.A. Abdellatif, W.A.A. Fadaly, Y.A.M.M. Elshaier, W.A.M.Ali and G.M. Kamel, Non-Acidic 1,3,4-Trisubstituted-Pyrazole Derivatives as Lonazolac Analogs with Promising COX-2 Selectivity, Anti-Inflammatory Activity and Gastric Safety Profile, Bioorg. Chem., 77, 568 (2018); https://doi.org/10.1016/j.bioorg.2018.02.018
- M. Baumann, I.R. Baxendale, S.V. Ley and N. Nikbin, An Overview of the Key Routes to the Bestselling 5-Membered Ring Heterocyclic Pharmaceuticals, Beilstein J. Org. Chem., 7, 442 (2011); https://doi.org/10.3762/bjoc.7.57
- K. Karrouchi, S. Radi, Y. Ramli, J. Taoufik, Y.N. Mabkhot, F.A. Al-Aizari and M. Ansar, Synthesis and Pharmacological Activities of Pyrazole Derivatives: A Review, Molecules, 23, 134 (2018); https://doi.org/10.3390/molecules23010134
- E. Takabatake, R. Kodama, Y. Tanaka, R. Dohmori, H. Tachizawa and T. Naito, The Metabolic Fate of 1-(4-Methoxy-6-methyl-2-pyrimidinyl)-3-methyl-5-methoxypyrazole (Mepirizole, DA-398) in Rats and Rabbits, Chem. Pharm. Bull. (Tokyo), 18, 1900 (1970); https://doi.org/10.1248/cpb.18.1900
- R. Goertz and T. Appelboom, Blocking of Mononuclear Cell Activation by Lonazolac, Int. J. Tissue React., 7, 263 (1985).
- J.A. Escario, A.M. Igea, M. Contreras, A.R. Martinez-Fernandez, R. Claramunt and C. Lopez, Antiparasitic Activity of Nine Pyrazole Derivatives against Trichomonas vaginalis, Entamoeba invadens and Plasmodium berghei, Ann. Trop. Med. Parasitol., 82, 257 (1988); https://doi.org/10.1080/00034983.1988.11812241
- D. Dumanovic, J. Jovanovic, D. Sužnjevic, M. Erceg and P. Zuman, Polarographic and Electrochemical Studies of Some Aromatic and Hetero-cyclic Nitro Compounds, Part II: Polarographic and Voltammetric Reduction of Some Nitramines, Pyrazolium and Imidazolium Nitro Derivatives, Electroanalysis, 4, 795 (1992); https://doi.org/10.1002/elan.1140040809
- A.J. Farre and J. Frigola, Drugs Future, 19, 651 (1994); https://doi.org/10.1358/dof.1994.019.07.254340
- A.M. Cuadro, J. Elguero and P. Navarro, Binuclear Pyrazoles. I. Synthesis and Cytotoxic Activity of 1,1¢-Dibenzyl and 1,1¢-Dihydroxymethyl 4,4¢-Bispyrazoles, Chem. Pharm. Bull. (Tokyo), 33, 2535 (1985); https://doi.org/10.1248/cpb.33.2535
- A.A. Chene, R. Deignier, J. Vors, J. Mortier, R. Cantegrill and D. Croisat, Eur. Pat., 17, 538156 (1993).
- R.N. Mahajan, F.H. Havaldar and P.S. Fernandes, Syntheses and Biological Activity of Heterocycles Derived from 3-Methoxy-1-phenyl-1H-pyrazole-5-carboxylate, J. Indian Chem. Soc., 68, 245 (1981).
- D.M. Bailey, P.E. Hansen, A.G. Hlavac, E.R. Baizman, A.F. DeFelice, J. Pearl and M.E. Feigenson, 3,4-Diphenyl-1H-pyrazole-1-propanamine Antidepressants, J. Med. Chem., 28, 256 (1985); https://doi.org/10.1021/jm00380a020
- K.R.S. Reddy, G. Srimannarayana and N.V. Subba Rao, Search for Physiologically Active Compounds Part XXVII. Synthesis of 2-[4-(1, 3-Diphenyl)pyrazolyl]-3-methoxychromones, Proc. Ind. Acad. Sci. Sec. A, 81, 197 (1975); https://doi.org/10.1007/BF03051142
- M. Benard, E. Hulley, H. Molenda and K. Stochla, Azoles. 17. b-(4-Pyrazol)acrylic and Propionic Acids and their Anti-Inflammatory Activity, Pharmazie, 41, 560 (1986).
- V.S. Chernyavichus, A.G. Odinets, A.E. Sausyn’, A.Ya. Berzinya and R.M. Zolotoyabko, Khim. Farm. Zh., 21, 959 (1987).
- N.K. Terrett, A.S. Bell, D. Brown and P. Ellis, Sildenafil (VIAGRATM), a Potent and Selective Inhibitor of Type 5 cGMP Phosphodiesterase with Utility for the Treatment of Male Erectile Dysfunction, Bioorg. Med. Chem. Lett., 6, 1819 (1996); https://doi.org/10.1016/0960-894X(96)00323-X
- J. Elgureo, A. R. Kartritzky and C.W. Rees, Comprehensive Hetrocyclic Chemistry, Pergamon Press: New York, vol. 5, p. 291 (1984).
- K.L. Kees, J.J. Fitzgerald, K.E. Steiner, J.F. Mattes, B. Mihan, T. Tosi, D. Mondoro and M.L. McCaleb, New Potent Antihyperglycemic Agents in db/db Mice: Synthesis and Structure Activity Relationship Studies of (4-Substituted benzyl)(trifluoromethyl)-pyrazoles and -pyrazolones, J. Med. Chem., 39, 3920 (1996); https://doi.org/10.1021/jm960444z
- K.L. Kees, T.J. Caggiano, K.E. Steiner, J.J. Fitzgerald Jr., M.J. Kates, T.E. Christos, J.M. Kulishoff, R.D. Moore and M.L. McCaleb, Studies on New Acidic Azoles as Glucose-Lowering Agents in Obese, Diabetic db/db Mice, J. Med. Chem., 38, 617 (1995); https://doi.org/10.1021/jm00004a008
- K. Ramalingam, G.X. Thyvelikakath, K.D. Berlin, R.W. Chesnut, R.A. Brown, N.N. Durham, S.E. Ealick and D. Van der Helm, Synthesis and Biological Activity of Some Derivatives of Thiochroman-4-one and Tetrahydrothiapyran-4-one, J. Med. Chem., 20, 847 (1977); https://doi.org/10.1021/jm00216a024
- R.E. Brown and J. Shavrel Jr., Substituted Benzopyranopyrazoles, US Patent 3,624,102A (1972).
- J.G. Lombardino and I.G. Otterrness, Novel Immunosuppressive Agents. Potent Immunological Activity of Some Benzothiopyrano[4,3-c]-pyrazol-3-ones, J. Med. Chem., 24, 830 (1981); https://doi.org/10.1021/jm00139a012
- R.H. Wiley and A. Weissberger, Pyrazoles, Pyrazolines, Indazoles and Condensed Rings: In The Chemistry of Hetrocyclic Compounds, Interscience Publishers: New York, vol. 22, p. 180 (1967).
- A. Levai and G. Toth, Nitrogen-Containing Heterocyclic Compounds from Exocyclic a,b-Unsaturated Ketones, Trends Hetrocycl. Chem., 4, 89 (1995).
- A. Levai, Khim. Geterotsikl. Soedin., 747 (1997).
- B. Stanovnik, 2-Substituted 3-Dimethylamino- and -3-Cyanopropenoates in the Synthesis of Heterocyclic Systems, J. Heterocycl. Chem., 36, 1581 (1999); https://doi.org/10.1002/jhet.5570360619
- F. Kallay, G. Janzso and I. Koczor, The Reaction of Flavanone with Hydrazine, Tetrahedron, 21, 19 (1965); https://doi.org/10.1016/S0040-4020(01)82197-9
- A. Radi, S. Radi and B. Hammouti, Pyrazole Derivatives with N-Pivot Functionalized Donor-Group: Synthesis and Preliminary Metals Binding Properties, J. Mater. Environ. Sci., 1, 96 (2010).
- J.R. Breen, G. Sandford, D.S. Yufit, J.A.K. Howard, J. Fray and B. Patel, Continuous Gas/Liquid-Liquid/Liquid Flow Synthesis of 4-Fluoropyrazole Derivatives by Selective Direct Fluorination, Beilstein J. Org. Chem., 7, 1048 (2011); https://doi.org/10.3762/bjoc.7.120
- S.K. Sahu, M. Banerjee, A. Samantray, C. Behera and M.A. Azam, Synthesis, Analgesic, Anti-inflammatory and Antimicrobial Activities of Some Novel Pyrazoline Derivatives, Trop. J. Pharm. Res., 7, 961 (2008); https://doi.org/10.4314/tjpr.v7i2.14664
- A. Mathew, M.L. Sheeja, T. Arunkumar and K. Radha, Design, Synthesis and Biological Evaluation of Pyrazole Analogues of Natural Piperine, Hygeia J. Drugs Med., 3, 48 (2013).
- S.E. Ahmet, E. Akbas and M.K. Sener, Synthesis and Some Reactions of 4-Benzoyl-5-phenyl-1-pyridin-2-yl-1H-pyrazole-3-carboxylic acid, Turk. J. Chem., 28, 271 (2004).
References
N.E. Santos, A.R.F. Carreira, V.L.M. Silva and S.S. Braga, Natural and Biomimetic Antitumor Pyrazoles, A Perspective, Molecules, 25, 1364 (2020); https://doi.org/10.3390/molecules25061364
A. Olyaei and M. Sadeghpour, Recent Developments in the Synthesis and Applications of Furopyrazoles, New J. Chem., 44, 14791 (2020); https://doi.org/10.1039/D0NJ02178D
N. Sugimoto, H. Watanabe and A. Ide, The Synthesis of L-a-Amino-b-(pyrazolyl-N)propionic Acid in Citrullus vulgaris, Tetrahedron, 11, 231 (1960); https://doi.org/10.1016/S0040-4020(01)93171-0
J.G. Buchanan, A. Stobie and R.H. Wightman, C-Nucleoside Studies. Part 14. A New Synthesis of Pyrazofurin, J. Chem. Soc., Perkin Trans., 2374 (1981); https://doi.org/10.1039/p19810002374
A. Morimoto, K. Noda, T. Watanabe and H. Takasugi, The Total Synthesis of Withasomnine, A Unique Pyrazole Alkaloid, Tetrahedron Lett., 9, 5707 (1968); https://doi.org/10.1016/S0040-4039(00)70757-X
K.R.A. Abdellatif, W.A.A. Fadaly, Y.A.M.M. Elshaier, W.A.M.Ali and G.M. Kamel, Non-Acidic 1,3,4-Trisubstituted-Pyrazole Derivatives as Lonazolac Analogs with Promising COX-2 Selectivity, Anti-Inflammatory Activity and Gastric Safety Profile, Bioorg. Chem., 77, 568 (2018); https://doi.org/10.1016/j.bioorg.2018.02.018
M. Baumann, I.R. Baxendale, S.V. Ley and N. Nikbin, An Overview of the Key Routes to the Bestselling 5-Membered Ring Heterocyclic Pharmaceuticals, Beilstein J. Org. Chem., 7, 442 (2011); https://doi.org/10.3762/bjoc.7.57
K. Karrouchi, S. Radi, Y. Ramli, J. Taoufik, Y.N. Mabkhot, F.A. Al-Aizari and M. Ansar, Synthesis and Pharmacological Activities of Pyrazole Derivatives: A Review, Molecules, 23, 134 (2018); https://doi.org/10.3390/molecules23010134
E. Takabatake, R. Kodama, Y. Tanaka, R. Dohmori, H. Tachizawa and T. Naito, The Metabolic Fate of 1-(4-Methoxy-6-methyl-2-pyrimidinyl)-3-methyl-5-methoxypyrazole (Mepirizole, DA-398) in Rats and Rabbits, Chem. Pharm. Bull. (Tokyo), 18, 1900 (1970); https://doi.org/10.1248/cpb.18.1900
R. Goertz and T. Appelboom, Blocking of Mononuclear Cell Activation by Lonazolac, Int. J. Tissue React., 7, 263 (1985).
J.A. Escario, A.M. Igea, M. Contreras, A.R. Martinez-Fernandez, R. Claramunt and C. Lopez, Antiparasitic Activity of Nine Pyrazole Derivatives against Trichomonas vaginalis, Entamoeba invadens and Plasmodium berghei, Ann. Trop. Med. Parasitol., 82, 257 (1988); https://doi.org/10.1080/00034983.1988.11812241
D. Dumanovic, J. Jovanovic, D. Sužnjevic, M. Erceg and P. Zuman, Polarographic and Electrochemical Studies of Some Aromatic and Hetero-cyclic Nitro Compounds, Part II: Polarographic and Voltammetric Reduction of Some Nitramines, Pyrazolium and Imidazolium Nitro Derivatives, Electroanalysis, 4, 795 (1992); https://doi.org/10.1002/elan.1140040809
A.J. Farre and J. Frigola, Drugs Future, 19, 651 (1994); https://doi.org/10.1358/dof.1994.019.07.254340
A.M. Cuadro, J. Elguero and P. Navarro, Binuclear Pyrazoles. I. Synthesis and Cytotoxic Activity of 1,1¢-Dibenzyl and 1,1¢-Dihydroxymethyl 4,4¢-Bispyrazoles, Chem. Pharm. Bull. (Tokyo), 33, 2535 (1985); https://doi.org/10.1248/cpb.33.2535
A.A. Chene, R. Deignier, J. Vors, J. Mortier, R. Cantegrill and D. Croisat, Eur. Pat., 17, 538156 (1993).
R.N. Mahajan, F.H. Havaldar and P.S. Fernandes, Syntheses and Biological Activity of Heterocycles Derived from 3-Methoxy-1-phenyl-1H-pyrazole-5-carboxylate, J. Indian Chem. Soc., 68, 245 (1981).
D.M. Bailey, P.E. Hansen, A.G. Hlavac, E.R. Baizman, A.F. DeFelice, J. Pearl and M.E. Feigenson, 3,4-Diphenyl-1H-pyrazole-1-propanamine Antidepressants, J. Med. Chem., 28, 256 (1985); https://doi.org/10.1021/jm00380a020
K.R.S. Reddy, G. Srimannarayana and N.V. Subba Rao, Search for Physiologically Active Compounds Part XXVII. Synthesis of 2-[4-(1, 3-Diphenyl)pyrazolyl]-3-methoxychromones, Proc. Ind. Acad. Sci. Sec. A, 81, 197 (1975); https://doi.org/10.1007/BF03051142
M. Benard, E. Hulley, H. Molenda and K. Stochla, Azoles. 17. b-(4-Pyrazol)acrylic and Propionic Acids and their Anti-Inflammatory Activity, Pharmazie, 41, 560 (1986).
V.S. Chernyavichus, A.G. Odinets, A.E. Sausyn’, A.Ya. Berzinya and R.M. Zolotoyabko, Khim. Farm. Zh., 21, 959 (1987).
N.K. Terrett, A.S. Bell, D. Brown and P. Ellis, Sildenafil (VIAGRATM), a Potent and Selective Inhibitor of Type 5 cGMP Phosphodiesterase with Utility for the Treatment of Male Erectile Dysfunction, Bioorg. Med. Chem. Lett., 6, 1819 (1996); https://doi.org/10.1016/0960-894X(96)00323-X
J. Elgureo, A. R. Kartritzky and C.W. Rees, Comprehensive Hetrocyclic Chemistry, Pergamon Press: New York, vol. 5, p. 291 (1984).
K.L. Kees, J.J. Fitzgerald, K.E. Steiner, J.F. Mattes, B. Mihan, T. Tosi, D. Mondoro and M.L. McCaleb, New Potent Antihyperglycemic Agents in db/db Mice: Synthesis and Structure Activity Relationship Studies of (4-Substituted benzyl)(trifluoromethyl)-pyrazoles and -pyrazolones, J. Med. Chem., 39, 3920 (1996); https://doi.org/10.1021/jm960444z
K.L. Kees, T.J. Caggiano, K.E. Steiner, J.J. Fitzgerald Jr., M.J. Kates, T.E. Christos, J.M. Kulishoff, R.D. Moore and M.L. McCaleb, Studies on New Acidic Azoles as Glucose-Lowering Agents in Obese, Diabetic db/db Mice, J. Med. Chem., 38, 617 (1995); https://doi.org/10.1021/jm00004a008
K. Ramalingam, G.X. Thyvelikakath, K.D. Berlin, R.W. Chesnut, R.A. Brown, N.N. Durham, S.E. Ealick and D. Van der Helm, Synthesis and Biological Activity of Some Derivatives of Thiochroman-4-one and Tetrahydrothiapyran-4-one, J. Med. Chem., 20, 847 (1977); https://doi.org/10.1021/jm00216a024
R.E. Brown and J. Shavrel Jr., Substituted Benzopyranopyrazoles, US Patent 3,624,102A (1972).
J.G. Lombardino and I.G. Otterrness, Novel Immunosuppressive Agents. Potent Immunological Activity of Some Benzothiopyrano[4,3-c]-pyrazol-3-ones, J. Med. Chem., 24, 830 (1981); https://doi.org/10.1021/jm00139a012
R.H. Wiley and A. Weissberger, Pyrazoles, Pyrazolines, Indazoles and Condensed Rings: In The Chemistry of Hetrocyclic Compounds, Interscience Publishers: New York, vol. 22, p. 180 (1967).
A. Levai and G. Toth, Nitrogen-Containing Heterocyclic Compounds from Exocyclic a,b-Unsaturated Ketones, Trends Hetrocycl. Chem., 4, 89 (1995).
A. Levai, Khim. Geterotsikl. Soedin., 747 (1997).
B. Stanovnik, 2-Substituted 3-Dimethylamino- and -3-Cyanopropenoates in the Synthesis of Heterocyclic Systems, J. Heterocycl. Chem., 36, 1581 (1999); https://doi.org/10.1002/jhet.5570360619
F. Kallay, G. Janzso and I. Koczor, The Reaction of Flavanone with Hydrazine, Tetrahedron, 21, 19 (1965); https://doi.org/10.1016/S0040-4020(01)82197-9
A. Radi, S. Radi and B. Hammouti, Pyrazole Derivatives with N-Pivot Functionalized Donor-Group: Synthesis and Preliminary Metals Binding Properties, J. Mater. Environ. Sci., 1, 96 (2010).
J.R. Breen, G. Sandford, D.S. Yufit, J.A.K. Howard, J. Fray and B. Patel, Continuous Gas/Liquid-Liquid/Liquid Flow Synthesis of 4-Fluoropyrazole Derivatives by Selective Direct Fluorination, Beilstein J. Org. Chem., 7, 1048 (2011); https://doi.org/10.3762/bjoc.7.120
S.K. Sahu, M. Banerjee, A. Samantray, C. Behera and M.A. Azam, Synthesis, Analgesic, Anti-inflammatory and Antimicrobial Activities of Some Novel Pyrazoline Derivatives, Trop. J. Pharm. Res., 7, 961 (2008); https://doi.org/10.4314/tjpr.v7i2.14664
A. Mathew, M.L. Sheeja, T. Arunkumar and K. Radha, Design, Synthesis and Biological Evaluation of Pyrazole Analogues of Natural Piperine, Hygeia J. Drugs Med., 3, 48 (2013).
S.E. Ahmet, E. Akbas and M.K. Sener, Synthesis and Some Reactions of 4-Benzoyl-5-phenyl-1-pyridin-2-yl-1H-pyrazole-3-carboxylic acid, Turk. J. Chem., 28, 271 (2004).