One‐Pot Synthesis of Oxime Derivatives of 1,3‐Diphenylpyrazole‐4‐carboxaldehydes from Acetophenone Phenylhydrazones Using Vilsmeier–Haack Reagent

References

• Jones , G. and Stanforth , S. P. 2001 . The Vilsmeier reaction of fully conjugated carbocycles and heterocycles . Org. React. , 49 : 1 – 315 .
   Google Scholar
• Meth‐Cohn , O. and Tarnowski , B. 1982 . Cyclizations under Vilsmeier conditions . Adv. Heterocycl. Chem. , 31 : 207 – 236 .
   Web of Science ®Google Scholar
• Perumal , P. T. 2001 . Synthesis of heterocyclic compounds using Vilsmeier reagent . J. Heterocycl. Chem. , 11 : 1 – 81 . Indian
   Web of Science ®Google Scholar
• Majo , V. J. and Perumal , P. T. 1998 . Intramolecular cyclization of azides by iminium species: A novel method for the construction of nitrogen heterocycles under Vilsmeier conditions . J. Org. Chem. , 63 : 7136 – 7142 .
   PubMed Web of Science ®Google Scholar
• Kira , M. A. , Abdel‐Rahman , M. O. and Gadalla , K. Z. 1969 . The Vilsmeier reaction—III, cyclization of hydrazones to pyrazoles . Tetrahedron Lett. , 10 : 109 – 110 .
   Google Scholar
• Prakash , O. , Kumar , R. , Bhardwaj , V. and Sharma , P. K. 2003 . Synthesis of 3‐aryl‐4‐formyl‐1‐(4,6‐dimethyl‐2‐pyrimidinyl)pyrazoles . Heterocycl. Commun. , 9 ( 5 ) : 515 – 518 .
   Google Scholar
• Kumar , A. , Prakash , O. , Kinger , M. and Singh , S. P. Synthesis of some new 1‐aryl‐4‐formyl‐3‐(4‐hydroxy‐6‐methyl‐2‐oxo‐2H‐pyran‐3‐yl)pyrazoles using Vilsmeier–Haack reaction . Can J. Chem. , (in press)
   Web of Science ®Google Scholar
• Selvi , S. and Perumal , P. T. 2002 . Facile synthesis of [1]benzopyrano[4,3‐c]pyrazoles, 1‐aryl‐3‐(2‐formamidophenyl)pyrazoles and 1‐aryl‐3‐phenyl‐4‐alkylpyrazoles using Vilsmeier reagent . Indian J. Chem. , 41B ( 9 ) : 1887 – 1893 .
   Google Scholar
• Elguero , J. 1984 . Comprehensive Heterocyclic Chemistry Edited by: Katritzky , A. Vol. 5 , 277 Oxford : Pregamon Press . Elguero, J. Comprehensive Heterocyclic Chemistry II; Shintai, I. Ed.; Elsevier: Oxford, 1986; Vol. 5, 3
   Google Scholar
• El‐Emary , T. I. and Bakhite , E. A. 1999 . Synthesis and biological screening of new 1,3‐diphenylpyrazoles with different heterocyclic moieties at position 4 . Pharmazie , 54 : 106 – 111 .
   PubMed Web of Science ®Google Scholar
• Bratenko , M. K. , Vovk , M. V. and Sydorchuk , I. J. 1999 . Synthesis and antibacterial and antifungal activity of hydrazones and azines of 1‐phenyl‐3‐R‐4‐formylpyrazole . Farm. Zh. , : 68 – 71 .
   Google Scholar
• Hajicek , J. , Miller , V. , Pihera , P. , Hrbata , J. , Prehnal , A. , Krepelka , J. and Grimova , J. Method of 1,3‐diaryl‐pyrazol‐4‐ylacetic acid production (eg. Ionazolac) . Czech. CS 275459 B219920219 patent . Chem. Abstr. 120/8588
   Google Scholar
• Rathelot , P. , Azas , N. , El‐Kashef , H. , Delmas , F. , Giorgio , C. D. , David , P. T. and Maldonado , V. P. 2002 . 1,3‐Diphenylpyrazoles: Synthesis and antiparasitic activities of azomethine derivatives . Eur. J. Med. Chem. , 37 : 671 – 679 .
   PubMed Web of Science ®Google Scholar
• Cottineau , B. , Toto , P. , Marot , C. , Pipaud , A. and Chenault , J. 2002 . Synthesis and hypoglycemic evaluation of substituted pyrazole‐4‐carboxylic acids . Biorg. Med. Chem. Lett. , 12 : 2105 – 2108 .
   PubMed Web of Science ®Google Scholar
• Soledad , C. P. M. and Zaharia , I. L. 2001 . Unprecedented Vilsmeier formylation: Expedient syntheses of the cruciferous phytolexins sinalexin and brassilexin and discovery of a new heteroaromatic ring system . Org. Lett. , 3 ( 8 ) : 1213 – 1216 .
   Web of Science ®Google Scholar
• Moriarty , R. M. 2005 . Organohypervalent iodine: Development, applications and future directions . J. Org. Chem. , 70 : 2893 – 2903 .
   PubMed Web of Science ®Google Scholar
• Koser , G. F. 2004 . The synthesis of heterocyclic compounds with hypervalent organoiodine reagents . Adv. Heterocycl. Chem. , 86 : 225 – 292 .
   Web of Science ®Google Scholar
• Prakash , O. 1995 . Organoiodine(III) and thallium(III) reagents in organic synthesis: Useful methodologies based on oxidative rearrangements . Aldrichimica Acta , 28 : 63 – 71 .
   Web of Science ®Google Scholar
• Moriarty , R. M. , Chany II , C. J. and Kosmeder II , J. W. 1995 . Encyclopedia of Reagents in Organic Synthesis , Edited by: Paquette , L. A. Vol. 2 , 1479 – 1484 . Chichester : John Wiley & Sons Ltd. .
   Google Scholar