One-Pot Synthesis of Some New Semicarbazone, Thiosemicarbazone, and Hydrazone Derivatives of 1-Phenyl-3-Arylpyrazole-4-Carboxaldehyde from Acetophenone Phenylhydrazones Using Vilsmeier–Haack Reagent

REFERENCES

• Marson , C. M. Reactions of carbonyl compounds with (monohalo) methyleniminium salts (vilsmeier reagents) . Tetrahedron 1992 , 48 , 3659 .
   Web of Science ®Google Scholar
• (a) Meth-Cohn , O. The synthesis of pyridines, quinolines, and other related systems by the Vilsmeier and the reverse Vilsmeier method . Heterocycles 1993 , 35 , 539 ; (b) Guzman , A. ; Ronero , M. ; Maddox , M. L. ; Machowski , J. M. Vilsmeier–Haack reaction with glutarimides: Synthesis of 2,6-dichloro-1,4-dihydropyridine-3,5-dicarboxaldehydes . J. Org. chem . 1990 , 55 , 5793 ; (c) Mahatta , P. K. ; Venktash , C. ; Shyam kumar , U. K. ; Ila , H. ; Junjappa , H. Reaction of -oxoketene-n,s-arylaminoacetals with Vilsmeier reagents: An efficient route to highly functionalized quinolines and their benzo/hetero-fused analogues . J. Org. Chem. 2003 , 68 , 3966 ; (d) Katrizky , A. R. ; Arend , M. A. Convenient and highly regioselective one-pot synthesis of quinolines by addition of a Vilsmeier-type reagent to n-arylimines . J. Org. Chem. 1998 , 63 , 9989 .
   Web of Science ®Google Scholar
• Kira , M. A. ; Abdel-Rahman , M. O. ; Gadalla , K. Z. The Vilsmeier–Haack reaction III: Cyclization of hydrazones to pyrazoles . Tetrahedron Lett. 1969 , 10 , 109 .
   Google Scholar
• (a) Dimmock , J. R. ; Puthucode , R. N. ; Smith , J. M. ; Hetherington , M. ; Quail , J.W. ; Pugazhenthi , U. ; Lechler , T. ; Stables , J. P. (Aryloxy)aryl semicarbazones and related compounds: A novel class of anticonvulsant agents possessing high activity in the maximal electroshock screen. J. Med. Chem. 1996 , 39 , 3984 ; (b) Dimmock , J. R. ; Vashishtha , S. C. ; Stables , J. P. Anticonvulsant properties of various acetylhydrazones, oxamoylhydrazones, and semicarbazones derived from aromatic and unsaturated carbonyl compounds. Eur J. Med. Chem. 2000 , 35 , 241 ; (c) Yogeeswari , P. ; Sriram , D. ; Thirumurugan , R. ; Reghavendran , J. V. ; Sudhan , K. ; Kumar , R. P. ; Stables , J. Discovery of N-(2,6-dimethylphenyl)-substituted semicarbazones as anticonvulsants: Hybrid pharmacophore-based design. J. Med. Chem. 2005 , 48 , 6202 ; (d) Yogeeswari , P. ; Sriram , D. ; Saxena , A. ; Thirumurugan , R. ; Stables , J. 2,4-Dimethoxyphenylsemicarbazones with anticonvulsant activity against three animal models of seizures: Synthesis and pharmacological evaluation. Biorg. Med. Chem. 2006 , 14 , 3106 ; (e) Yogeeswari , P. ; Thirumurugan , R. ; Sriram , D. ; Suniljit , L. R. J. ; Reghavendran , J. V. ; Kavya , R. ; Rakhera , K. ; Stables , J. Synthesis of N4-(2,4-dimethylphenyl) semicarbazones as 4-aminobutyrate aminotransferase inhibitors . Acta Pharm. 2006 , 56 , 259 . (f) Berlado , H. ; Gambino , D. The wide pharmacological versatility of semicarbazones, thiosemicarbazones, and their metal complexes . Mini-Rev. Med. Chem. 2004 , 4 ( 1 ), 31 .
   PubMedGoogle Scholar
• Bal , T. ; Atasever , B. ; Solakoglu , Z. ; Kuruca , S. E. ; Wkiiseven , B. Synthesis, characterization, and cytotoxic properties of the N 1,N 4-diarylidene-S-methyl-thiosemicarbazone chelates with Fe(III) and Ni(II) . Eur. J. Med. Chem. 2007 , 42 , 161 .
   PubMed Web of Science ®Google Scholar
• (a) Prakash , O. ; Kumar , R. ; Bhardwaz , V. ; Sharma , P. K. Synthesis of some new 3-aryl-4-formyl-1-(4,6-dimethyl-2-pyrimidinyl)pyrazoles using Vilsmeier–Haack reaction . Hetcrocycl. Commun. 2003 , 9 ( 5 ), 515 ; (b) Kumar , A. ; Prakash , O. ; Kinger , M. ; Singh , S. P. Synthesis of some new 1-aryl-4-formyl-3-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)pyrazoles using the Vilsmeier–Haack reaction—Isolation of the key intermediate 1-aryl-3-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)pyrazoles . Can. J. Chem. 2006 , 84 , 438 .
   Google Scholar
• (a) Loncle , C. ; Brunel , J. M. ; Vidal , N. ; Dherbomez , M. ; Letourneux , Y. Synthesis and antifungal activity of cholesterol-hydrazone derivatives . Eur. J. Med. Chem. 2004 , 39 , 1067 (b) Vicini , P. ; Zani , F. ; Cozzini, P: Doytchinova , I. Hydrazones of 1,2-benzisothiazole hydrazides: Synthesis, antimicrobial activity, and QSAR investigations . Eur. J. Med. Chem. 2002 , 37 , 553 .
   PubMed Web of Science ®Google Scholar
• (a) Popp , F. D. Potential anticonvulsant, XII: Anticonvulsant activity of some aldehyde derivatives . Eur. J. Med. Chem. 1989 , 24 , 313 (b) Sridhar , S. K. ; Pandeya , S. N. ; Stables , J. P. ; Atmakuru , R. The influence of particles of a minor component on the matrix strength of sodium chloride . Eur. J. Pharma. Sci. 2002 , 16 , 129 (c) Kuchukguzel , S. G. ; Mazi , A. ; Sahin , F. ; Ozturk , S. ; Stables , J. P. Synthesis and biological activities of diflunisal hydrazide–hydrazones . Eur. J. Med. Chem. 2003 , 38 , 1005 .
   Google Scholar
• (a) Kuchukguzel , S. G. ; Rollas , S. ; Kuchukguzel , I. ; Kiraz , M. Synthesis and antimycobacterial activity of some coupling products from 4-aminobenzoic acid hydrazones . Eur. J. Med. Chem. 1999 , 34 , 1093 (b) Patole , J. ; Sandbhor , U. ; Padhye , S. ; Deobagkar , D. N. ; Arison , C. E. ; Powell , A. Structural chemistry and in vitro antitubercular activity of acetylpyridine benzoyl hydrazone and its copper complex against Mycobacterium smegmatis . Biorg. Med. Chem. Lett. 2003 , 13 , 51 (c) Rando , D. G. ; Sato , D. N. ; Siqueira , L. ; Malvezzi , A. ; Leite , C. Q. F. ; Amaral , A. T. ; Ferreira , E. J. ; Tavares , L. C. Synthesis, DNA binding, topoisomerases inhibition and cytotoxic properties of 4-arylcarboxamidopyrrolo-2-carboxyanilides . Biorg. Med. Chem. Lett. 2002 , 10 , 557 .
   Google Scholar
• Prakash , O. ; Pannu , K. ; Kaur , H. ; Naithani , R. One-pot synthesis of oxime derivatives of 1,3-diphenylpyrazole-4-carboxaldehydes from acetophenone phenylhydrazones using Vilsmeier–Haack reagent . Synth. Commun. 2006 , 36 , 3479 .
   Web of Science ®Google Scholar