THE PREPARATION OF 3-(2-PHENYLETHENYL)-1H-PYRAZOLES FROM DILITHIATED (3E)-4-PHENYL-3-BUTEN-2-ONE HYDRAZONES

The phenyl-, carbomethoxy-, and carboethoxy-hydrazones of (3E)-4-phenyl-3-buten-2-one [benzalacetone] were treated with excess lithium diisopropylamide, and the resulting 1,4-dianions were condensed with several aromatic esters, followed by acid cyclization of C-acylated intermediates, to afford substituted 3-(2-phenylethenyl)-1H-pyrazoles [3-styryl-pyrazoles].

[1]  D. Hurst,et al.  A New Series of Proton/Charge Transfer Molecules: Synthesis and Spectral Studies of 2‐(5‐Aryl‐1‐carbomethoxy‐1H‐pyrazol‐3‐yl)phenols , 1999 .

[2]  David W. Evans.  The Systematic Identification of Organic Compounds, 7th Edition (Shriner, R. L.; Hermann, C. K. F.; Morrill, T. C.; Curtin, D. Y.; Fuson, R. C.) , 1999 .

[3]  D. Hurst,et al.  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 , 1999 .

[4]  K. Schey,et al.  The preparation of N-(1H-pyrazol-3-yl)arylamides and 1H-pyrazol-3-amines from polylithiated C(α),N-thiosemicarbazones and C(α),N-semicarbazones , 1997 .

[5]  O. Prakash,et al.  HYPERVALENT IODINE OXIDATION OF 1,3,5-TRISUBSTITUTED PYRAZOLINES : A FACILE SYNTHESIS OF 1,3,5-TRISUBSTITUTED PYRAZOLES , 1997 .

[6]  M. A. Hines,et al.  The Preparation of 1H-Pyrazole-1-carboxylic Acid, 1, 1-Dimethylethyl Esters from Dilithiated C(α), N-Hydrazones of Hydrazinecarboxylic Acid, 1, 1-Dimethylethyl Ester , 1996 .

[7]  A. Church,et al.  The Preparation of 1H-Pyrazole-5-propanoic and 1H-Pyrazole-5-butanoic Acids from Dilithiated C(α),N-Carboalkoxyhydrazones and Succinic or Glutaric Acid Anhydrides , 1996 .

[8]  M. Soufiaoui,et al.  Conversion des cis- et trans-pyrazolines en pyrazoles sur support minéral imprégné de nitrate ferrique ou cuivrique , 1995 .

[9]  A. Hosomi,et al.  The Preparation of N-Acylpyrazoles and Their Behavior Toward Alcohols , 1994 .

[10]  Kiyoshi Tanaka,et al.  Directed ortho lithiation in the reactions of 3,5-dimethyl- and 5-trifluoromethyl-1-phenylpyrazoles with butyllithium , 1992 .

[11]  K. Takagi,et al.  Reactions of triacetylmethane with monosubstituted hydrazines and amidine analogues. Syntheses of 4-acetyl-3,5-dimethylpyrazole amidinohydrazone and 1,3,5-triazine derivatives , 1990 .

[12]  M. Soufiaoui,et al.  Cycloaddition dipolaire 1,3 des 4-arylidene oxazol-5- ones avec la diphenylnitrilimine , 1990 .

[13]  M. A. Hines,et al.  The Preparation of Substituted 5H-Pyrazolo[1,5-c] [1,3]-Benzoxazin-5-ones from the Trianions of Certain Hydroxyphenylcarboethoxyhydrazones , 1990 .

[14]  D. C. Duncan,et al.  The preparation of N-carboalkoxypyrazoles and N-phenylpyrazoles from C(α)-dianions of carboalkoxyhydrazones and phenylhydrazones , 1987 .

[15]  A. Huff,et al.  The preparation of selected benzopyrano[3,4‐b]pyrazoles by the condensation of c(α), n‐dilithiocarboalkoxyhydrazones and salicylate esters , 1986 .

[16]  Frank C. H. Waters,et al.  The preparation of phenacylpyrazoles, acylpyrazoles, imidazolylisoxazoles and imidazolylpyrazoles from C(α)-dianions of oximes, phenylhydrazones and acylhydrazones , 1985 .

[17]  A. Huff,et al.  THE PREPARATION AND REACTIONS OF C(α),N-DILITHIOCARBOALKOXYHYDRAZONES , 1984 .

[18]  J. Elguero.  4.04 – Pyrazoles and their Benzo Derivatives , 1984 .

[19]  O. M. Radul,et al.  Khim. Geterotsikl. Soedin. , 1982 .

[20]  C. F. Beam,et al.  The preparation of 5-phenacylisoxazoles and 5-hydroxyphenyl-isoxazoles and -pyrazoles by the condensation of C(a)-dianions with ethyl benzoylacetate and methyl salicylate , 1982 .

[21]  C. F. Beam,et al.  An improved synthesis of 3,5-disubstituted isoxazoles and pyrazoles from C(α),O-dilithiooximes and C(α),N-dilithiophenylhydrazones , 1980 .

[22]  J. Shah,et al.  Oxidative dehydrogenation of pyrazolines with cobalt(II) and oxygen , 1978 .

[23]  J. Grimshaw,et al.  Electrochemical reactions. Part XIII. Reduction of some styrylpyrazole derivatives , 1973 .

[24]  T. Mabry,et al.  The Systematic Identification of Flavonoids , 1970, Springer Berlin Heidelberg.

[25]  M. V. George,et al.  Oxidation with metal oxides—II : Oxidation of chalcone phenylhydrazones, pyrazolines, o-aminobenzylidine anils and o-hydroxy benzylidine anils with manganese dioxide , 1968 .

[26]  R. Shriner.  The Systematic Identification of Organic Compounds: , 1936, Nature.