Multicomponent Reaction for Synthesis of N-Arylsulfonyl Pyrazoles

REFERENCES

• Elguero , J. Comprehensive Heterocyclic Chemistry ; R. A. Kartitzky , W. C. Rees , and V. F. E. Scriven (Eds.); Pergamon : Oxford , 1996 ; vol. 5 .
   Google Scholar
• Lee , Y. K. ; Kim , M. J. Regioselective synthesis of 1,3,4,5-tetrasubstituted pyrazoles from Baylis–Hillman adducts . Tetrahedron. Lett. 2003 , 44 , 6737 – 6740 .
   Web of Science ®Google Scholar
• Francisco , Y. E. M. ; Seltzman , H. H. ; Gilliam , A. F. ; Mitchell , R. A. ; Rider , S. L. ; Pertwee , G. R. ; Stevenson , A. L. ; Thomas , F. B. Synthesis and structure–activity relationships of amide and hydrazide analogues of the cannabinoid CB1 receptor antagonist N-(piperidinyl)-5-(4-chlorophenyl)-1-pyrazole-3-carboxamide . J. Med. Chem. 2002 , 45 , 2708 – 2719 .
   PubMed Web of Science ®Google Scholar
• Haque , S. T. ; Tadesse , S. ; Marcinkeviciene , J. ; Rogers , J. M. ; Sizemore , C. ; Kopcho , M. L. ; Amsler , K. ; Ecret , D. L. ; Zhan , L. D. ; Hobbs , F. ; Slee , A. ; Trainor , L. G. ; Stern , M. A. ; Copeland , A. R. ; Combs , P. A. Parellel synthesis of potent, pyrazole-based inhibitors of helicobacter pylori dehydrogenase. J. Med. Chem. 2002, 45, 4669–4678.
   PubMed Web of Science ®Google Scholar
• Nakamura , T. ; Sato , M. ; Kakinuma , H. ; Miyata , N. ; Taniguchi , K. ; Bando , K. ; Koda , A. ; Kameo , K. Pyrazole and isoxazole derivatives as new, potent, and selective zo-hydroxy-5,8,11,14-eicosatetraenoic acid synthase inhibitors . J. Med. Chem. 2003 , 46 , 5416 – 5427 .
   PubMed Web of Science ®Google Scholar
• Komeda , S. ; Lutz , M. ; Spek , L. A. ; Chikuma , M. ; Reedijk , J. New antitumor-active azole-bridged dinuclear platinum complexes: Synthesis, characterization, crystal structure, and cytotoxic studies . Inorg. Chem. 2000 , 39 , 4230 – 4236 .
   PubMed Web of Science ®Google Scholar
• Kost , N. A. ; Granberg , I. I. Progress in pyrazole chemistry . Adv. Heterocycl. Chem. 1966 , 6 , 347 – 429 .
   Google Scholar
• Donohue , A. B. ; Michelotti , L. E. ; Reader , C. J. ; Reader , V. ; Stirling , M. ; Tice , M. C. Design, synthesis, and biological evaluation of a library of 1-(2-thiazolyl)-5-(trifluoromethyl)pyrazole-4-carboxamides . J. Comb. Chem. 2002 , 4 , 23 – 32 .
   PubMed Web of Science ®Google Scholar
• Aggarwal , K. V. ; de Vicente , J. ; Bonnert , V. R. A novel one-pot method for the preparation of pyrazoles by 1,3-dipolar cycloaddition of diazo compounds generated in situ . J. Org. Chem. 2003 , 68 , 5381 – 5383
   PubMed Web of Science ®Google Scholar
• Ahmed , M. S. M. ; Kobayashi , K. ; Mori , A. One-pot construction of pyrazoles and isoxazoles with palladium-catalyzed four-component coupling . Org. Lett. 2005 , 7 , 4487 – 4489 .
   PubMed Web of Science ®Google Scholar
• Yavari , I. ; Khalili , G. A diastereoselective synthesis of phosphorylated dihydro-1H-pyrazole from dialkylphosphites, acetylenic esters, and hydrazonoyl chlorides . Synlett 2010 , 12 , 1862 – 1864
   Web of Science ®Google Scholar
• Yavari , I. ; Khalili , G. ; Mirzaee , A. One-pot synthesis of functionalized 3-aryl-1-phenyl-1H-pyrazoles from hydrazonoyl chlorides and acetylenic esters in the presence of Ph3P . Helv. Chem. Acta 2010 , 93 , 277 – 280 .
   Web of Science ®Google Scholar
• Keith , M. J. ; Jacobsen , N. E. Asymmetric hydrocyanation of hydrazones catalyzed by lanthanide-PYBOX complexes . Org. Lett. 2004 , 6 , 153 – 155 .
   PubMed Web of Science ®Google Scholar
• Dadiboyena , S. ; Valente , E. J. ; Hamme II , A. T. Synthesis of novel pyrazoles via [2 + 3] dipolar cycloaddition using alkyne surrogates . Tetrahedron Lett. 2010 , 51 , 1341 – 1343 .
   PubMed Web of Science ®Google Scholar
• Ogawa , C. ; Konishi , H. ; Sugiura , M. ; Kobayashi , S. Phosphine oxides as efficient neutral coordinate-organocatalysts for stereoselectiveallylation of N-acylhydrazones . Org. Biomol. Chem. 2004 , 2 , 446 – 448 .
   PubMed Web of Science ®Google Scholar
• Zhao , I. G. ; Shi , M. DABCO-catalyzed reactions of hydrazones with activated olefins . Tetrahedron. 2005 , 61 , 7277 – 7288
   Web of Science ®Google Scholar
• Cacchi , S. ; La Torre , F. ; Misiti , D. N-Alkylation of tosylhydrazones through phase-transfer catalysis . Synthesis. 1977 , 301 – 303 .
   Web of Science ®Google Scholar
• Blair , P. A. ; Chang , S.-J. ; Shechter , H. Photolytic, thermal addition, and cycloaddition reactions of 2-diazo-5,6- and -3,8-disubstituted acenaphthenones . J. Org. Chem. 2004 , 69 , 7123 – 7133 .
   PubMed Web of Science ®Google Scholar
• Hashemi , S. A. Regioselective synthesis of (E)-3-[2-(arylmethylene)-1-(arylsulfonyl)hydrazino]-2-propenoates via the reaction of arylsulfonyl hydrazones and alkyl propiolates in the presence of PPh3 . Tetrahedron Lett. 2012 , 53 , 5141 – 5143 .
   Web of Science ®Google Scholar
• Islam , A. M. ; Abdel-Halim , A. M. ; Salama , M. A. Synthesis of some naphthalene-sulphonohydrazides and related compounds of potential biological activity . Egypt. J. Chem. 1987 , 29 , 405 – 409 .
   Google Scholar