Regioselective Synthesis of 1,3,5-Trisubstituted Pyrazoles

REFERENCES

• (a) Gilchrist , T. L. Heterocyclic Chemistry, , 3rd ed. ; Addison-Wesley Longman : London , 1998 ; (b) Azarifar , D. ; Shaebanzadeh , M. Synthesis and characterisation of new 3,5-dinaphthyl substituted 2-pyrazolines and study of their antimicrobial properties. Molecules 2002, 7, 885–895 .
   Google Scholar
• (a) Katayama , H. ; Oshiyama , T. Preparation and bioactivity of pyrazole derivatives as potential cross-linking agents . Can. J. Chem. 1997 , 75 , 913 – 919 ; (b) Faid , H. M. ; Mokhtar , H. M. Pyrazole derivatives with possible hypoglycemic activity . Ind. J. Chem. 1988 , 27B , 245 – 249 .
   Web of Science ®Google Scholar
• (a) Singh , S. P. ; Kumar , D. ; Prakash , O. ; Kapoor , R. P. Hypervalent iodine oxidation of 1,3,5-trisubstituted pyrazolines: A facile synthesis of 1,3,5-trisubstituted pyrazoles . Synth. Commun. 1997 , 27 ( 15 ), 2683 ; (b) Bhatnagar , I. ; George , M. V. Oxidation with metal oxides II: Oxidation of chalcone phenylhydrazones, pyrazolines, o-aminobenzylidine anils, and o-hydroxybenzylidine anils with manganese dioxide . Tetrahedron 1968 , 24 , 1293 ; (c) Gladstone , W. A. F. ; Norman , R. O. C. Reactions of lead tetra-acetate, part VII: Some reactions leading to pyrazoles . J. Chem. Soc., Chem. 1966 , 1536 ; (d) Sabitha , G. ; Kumar Reddy , G. S. K. ; Reddy , Ch. S. ; Fatima , N. ; Yadav , J. S. Zr(NO3)4: A versatile oxidizing agent for aromatization of Hantzsch 1,4-dihydropyridines and 1,3,5-trisubstituted pyrazolines . Synthesis 2003 , 8 , 1267 ; (e) Ponnala , S. ; Sahu , D. P. Iodine-mediated synthesis of 2-arylbenzoxazoles, 2-arylbenzimidazoles, and 1,3,5-trisubstituted pyrazoles . Synth. Commun. 2006 , 36 , 2189 ; (f) Nakamuchi , N. ; Kawashita , Y. ; Hayashi , M. Activated carbon-promoted oxidative aromatization of Hantzsch 1,4-dihydropyridines and 1,3,5-trisubstituted pyrazolines using molecular oxygen . Synthesis 2004 , 7 , 1015 .
   Web of Science ®Google Scholar
• (a) Aggarwal , R. ; Kumar , R. Iodobenzene diacetate–mediated oxidation of N-substituted hydrazones of chalcones: An efficient regioselective synthesis of 1,3,5-trisubstituted pyrazoles . Synth. Commun. 2009 , 39 , 2169 ; (b) Kovelesky , A. C. ; Shine , H. J. Oxidative cyclization of arylhydrazones of chalcones and benzalacetones to pyrazoles by thianthrene cation radical . J. Org. Chem. 1988 , 53 , 1973 ; (c) Tabakovic , I. ; Lacan , M. ; Damoni , S. Electrochemical syntheses of heterocyclic compounds III: Anodic oxidation of chalcone phenylhydrazone . Electrochim. Acta 1976 , 21 , 621 .
   Web of Science ®Google Scholar
• (a) Desai , V. ; Tilve , S. A novel and a convenient method for the synthesis of 3,5-diarylisoxazoles . Synth. Commun. 1999 , 29 , 3017 – 3020 ; (b) Kurangi , R. ; Kawthankar , R. ; Sawal , S. ; Desai , V. ; Tilve , S. Convenient synthesis of 3, 5-diarylisoxazoles . Synth. Commun. 2007 , 37 , 585 – 587 .
   Web of Science ®Google Scholar
• (a) Jedlovska , E. ; Fisera , L. ; Liptag , T. Regio- and stereoselectivity of aromatic and heteroaromatic nitrilimines in 1,3-dipolar cycloadditions . T. Chem. Pap. 2005 , 59 ( 5 ), 354 .
   Web of Science ®Google Scholar
• Rezende , C. M. ; Pizarro , C. ; Millan , D. Preparation, spectroscopic, and acidity properties of two hydrazones: An organic experiment. Quim. Nova. 2007, 30 (1), 229.
   Web of Science ®Google Scholar
• Harris , D. J. ; Kan , G. Y. P. ; Snieckus , V. The synthesis of 1, 2-diazepines from thiapyrylium salts . Can. J. Chem. 1974 , 52 , 2798 .
   Web of Science ®Google Scholar
• Morrocohi , S. ; Ricca , A. ; Zanarotti , A. New features of the reaction between nitrilimines and arylacetylenes . Tetrahedron Lett. 1970 , 3215 .
   Google Scholar
• Landge , S. M. ; Schmidt , A. ; Outerbridge , V. ; Torok , B. Synthesis of pyrazoles by a one-pot tandem cyclization–dehydrogenation approach on PD/C/K-10 catalyst . Synlett 2007 , 10 , 1600 .
   Google Scholar
• Azarifar , D. ; Zulfigol , M. A. ; Maleki , B. 1,3-Dibromo-5,5-dimethylhydantoin as a novel oxidizing agent for the oxidation of 1,3,5-trisubstituted pyrazolines under both heterogeneous as well as solvent-free conditions . Bull. Korean Chem. Soc. 2004 , 25 ( 1 ), 23 .
   Web of Science ®Google Scholar
• Zulfigol , M. A. ; Azarifar , D. ; Mallakpour , S. ; Baltork , I. M. ; Forghaniha , A. ; Haleki , B. Abdollahi-Alibeik , M. 4-(p-Chloro)phenyl-1,2,4-triazole-3,5-dione as a novel and reusable reagent for the oxidation of 1,3,5-trisubstituted pyrazolines under mild conditions . Tetrahedron Lett. 2006 , 47 , 833 .
   Web of Science ®Google Scholar
• Azarifar , D. ; Maleki , B. ; Sahraei , M. Microwave-promoted oxidation of 1,3,5-trisubstituted-4,5-dihydro-1H-pyrazoles by in situ generation of NO+ respectively from sodium nitrite and sodium nitrate in acetic acid . J. Heterocycl. Chem. 2008 , 45 , 563 .
   Web of Science ®Google Scholar
• Azarifar , D. ; Zulfigol , M. A. ; Maleki , B. Silica-supported-1,3-dibromo-5,5-dimethylhydantoin (DBH) as a useful reagent for microwave-assisted aromatization of 1,3,5-trisubstituted pyrazolines under solvent-free conditions . Synthesis 2004 , 11 , 1744 .
   Web of Science ®Google Scholar
• Jones , L. A. ; Hancock , C. K. ; Seligman , R. B. The reaction of 2,4-dinitrophenylhydrazone with some dicarbonyl compounds and α-substituted carbonyl compounds . J. Org. Chem. 1961 , 26 , 228 .
   Web of Science ®Google Scholar
• Shah , J. N. ; Shah , C. K. Oxidative dehydrogenation of pyrazolines with cobalt(II) and oxygen . J. Org. Chem. 1978 , 43 ( 6 ), 1266 .
   Web of Science ®Google Scholar
• Van Steeris , J. Nitration of dianisoylmethane and p-methoxydesoxybenzoin . Recueil des Travaux Chimiques des Pays-Bas et de la Belgique 1947 , 66 , 29 – 46 .
   Google Scholar
• Orlov , V. D. ; Shkumat , A. P. ; Kotlyar , V. N. Oxidation of 2-pyrazolines . Visnik Kharkivis'kogo Universitetu 1999 , 437 , 99 – 102 .
   Google Scholar
• Deng , X. ; Mani Neelakandha , S. Regioselective synthesis of 1,3,5-tri- and 1,3,4,5-tetrasubstituted pyrazole from N-arylhydrazones and nitroolefins . J. Org. Chem. 2008 , 73 ( 6 ), 2412 .
   PubMed Web of Science ®Google Scholar
• Gella , I. M. ; Amadu , R. ; Orlov , V. D. 2-Pyrazolines based on diarylidene-cyclohexanes: Synthesis and stereochemistry of partially hydrogenated N-arylindazoles . Visnik Kharkivis'kogo Universitetu 2001 , 532 , 103 – 108 .
   Google Scholar