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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 42, 2012 - Issue 13
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Original Articles

An Efficient Four-Component Synthesis of Multisubstituted Pyrano[2,3-c]pyrazole

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Pages 1959-1966 | Received 12 Aug 2010, Accepted 23 Dec 2010, Published online: 26 Mar 2012

REFERENCES

  • (a) Zora , M. ; Yucel , B. ; Acikalin , S. Synthesis of ferrocenyl quinones . Tetrahedron Lett. 2003 , 44 , 2237 – 2241 ; (b) Fan , X. ; Feng , D. ; Zhang , X. ; Wang , J. ; Loiseau , P. ; Audrei , G. ; Snoeck , R. ; Clercq , E. D. Practical and efficient synthesis of pyrano[3,2-c]pyridine, pyrano[4,3-b]pyran, and their hybrids with nucleoside as potential antiviral and antileishmanial agents . Bioorg. Med. Chem. Lett. 2010 , 20 , 809 – 813 .
  • (a) Weber , L. The application of multicomponent reactions in drug discovery . Curr. Med. Chem. 2002 , 9 , 1241 – 1253 ; (b) Bedair , A. H. ; Emam , H. A. ; El-Hady , N. A. ; Ahmed , K. A. R. ; El-Agrody , A. M. Synthesis and antimicrobial activities of novel naphtha[2,1-b]pyran, pyrano[2,3-d]pyrimidine, and pyrano[3,2-e][1,2,4]triazolo[2,3-c]-pyrimidine derivatives . Farmaco 2001 , 56 , 965 – 973 .
  • (a) Devi , I. ; Kumar , B. S. D. ; Bhuyan , P. J. A novel, three-component, one-pot synthesis of pyrano[2,3-d]pyrimidines and pyrido[2,3-d]pyrimidines using microwave heating in the solid state . Tetrahedron Lett. 2003 , 44 , 8307 – 8310 ; (b) Salama , T. A. ; Elmorsy , S. S. ; Khalil , A. M. ; Ismail , M. A. A SiCl4-ZnCl2-induced general, mild, and efficient one-pot, three-component synthesis of β-amido ketone libraries . Tetrahedron Lett. 2007 , 48 , 6199 – 6203 ; (c) Li , M. ; Sun , E. ; Wen , L. ; Wang , S. Synthesis and crystal structure of 3-benzoyl-7,7-dimethyl-4-phenyl-2-phenylamino-4,6,7,8-tetrahydro-chromen-5-one . Chin. J. Struct. Chem. 2007 , 26 , 385 – 388 .
  • (a) Adib , M. ; Sayahi , M. H. ; Nosrati , M. ; Zhu , L. G. A novel, one-pot, three-component synthesis of 4H-pyrido[1,2-a]pyrimidines . Tetrahedron Lett. 2007 , 48 , 4195 – 4198 ; (b) Magedov , I. V. ; Manpadi , M. ; Evdokimov , N. M. ; Elias , E. M. ; Rozhkova , E. ; Ogasawara , M. A. ; Bettale , J. D. ; Przhevalskii , N. M. ; Rogelj , S. ; Kornienko , A. Antiproliferative and apoptosis inducing properties of pyrano[2,3-c]pyridones accessible by a one-step multicomponent synthesis . Bioorg. Med. Chem. Lett. 2007 , 17 , 3872 – 3876 .
  • (a) Junek , H. ; Aigner , H. Reactions of tetracyanoethylene with heterocyclic compounds . Chem. Ber. 1973 , 106 , 914 – 921 ; (b) Tacconi , G. ; Gatti , G. ; Desimoni , G. ; Messori , V. J. A new route to 4H-pyrano[2,3-c]pyrazoles . Prakt. Chem. 1980 , 322 , 831 – 834 ; (c) Shestopalov , A. M. ; Emeliyanova , Y. M. ; Shestopalov , A. A. ; Rodinovskaya , L. A. ; Niazimbetova , Z. I. ; Evans , D. H. Cross-condensation of derivatives of cyanoacetic acid and carbonyl compounds, part 1: Single-stage synthesis of 1′-substituted 6-amino-spiro-4-(piperidine-4′)-2H,4H-pyrano[2,3-c]pyrazole-5-carbonitriles . Tetrahedron 2003 , 59 , 7491 – 7496 .
  • Shaabani , A. ; Sarvary , A. ; Rezayan , A. H. ; Keshipour , S. Synthesis of fully substituted pyrano[2,3-c]pyrazole derivatives via a multicomponent reaction of isocyanides . Tetrahedron 2009 , 65 , 3492 – 3495 .
  • Wang , J. L. ; Liu , D. ; Zhang , Z. J. ; Shan , S. ; Han , X. ; Srinivasula , S. M. ; Croce , C. M. ; Alnemri , E. S. ; Huang , Z. Structure-based discovery of an organic compound that binds bcl-2 protein and induces apoptosis of tumor cells . Proc. Natl. Acad. Sci. U.S.A. 2000 , 97 , 7124 – 7129 .
  • Zaki , M. E. A. ; Soliman , H. A. ; Hiekal , O. A. ; Rashad , A. E. Pyrazolopyrano-pyrimidines as a class of anti-inflammatory agents . Naturforsch C 2006 , 61 , 1 – 5 .
  • EI-Tamany , E. S. ; EI-Shahed , F. A. ; Mohamed , B. H. Synthesis and biological activity of some pyrazole derivatives . J. Serb. Chem. Soc. 1999 , 64 , 9 – 18 .
  • (a) Zhou , J. F. ; Tu , S. J. ; Zhu , H. Q. ; Zhi , S. J. A facile one pot synthesis of pyrano[2,3-c]pyrazole derivatives under microwave irradiation . Synth. Commun. 2002 , 32 , 3363 – 3366 ; (b) El-Assiery , S. A. ; Sayed , G. H. ; Fouda , A. Synthesis of some new annulated pyrazolo-pyrido (or pyrano) pyrimidine, pyrazolopyridine and pyranopyrazole derivatives . Acta Pharm. 2004 , 54 , 143 – 150 .
  • Ren , Z. J. ; Cao , W. ; Tong , W. ; Jin , Z. Solvent-free, one-pot synthesis of pyrano[2,3-c]pyrazole derivatives in the presence of KF · 2H2O by grinding. Synth. Commun. 2005, 35, 2509–2513.
  • Guo , S. B. ; Wang , S. X. ; Li , J. T. D,L-Proline-catalyzed one-pot synthesis of pyrans and pyrano[2,3-c]pyrazole derivatives by a grinding method under solventfree conditions . Synth. Commun. 2007 , 37 , 2111 – 2120 .
  • (a) Shestopalov , A. M. ; Shestopalov , A. A. ; Rodinovskaya , L. A. Multicomponent reactions of carbonyl compounds and derivatives of cyanoacetic acid: Synthesis of carbo- and heterocycles . Synthesis 2008 , 1 – 25 ; (b) Lehmann , F. ; Holm , M. ; Laufer , S. Three-component combinatorial synthesis of novel dihydropyrano[2,3-c]pyrazoles . J. Comb. Chem. 2008 , 10 , 364 – 367 .
  • Shestopalov , A. M. ; Emeliyanova , Y. M. ; Shestopalov , A. A. ; Rodinovskaya , L. A. ; Niazimbetova , Z. I. ; Evans , D. H. Cross-condensation of derivatives of cyanoacetic acid and carbonyl compounds, part 1: Single-stage synthesis of 10-substituted 6-amino-spiro-4-(piperidine-40)-2H,4H-pyrano[2,3-c]pyrazole-5-carbonitriles . Tetrahedron 2003 , 59 , 7491 – 7496 .
  • (a) Litvinov , Y. M. ; Shestopalov , A. A. ; Rodinovskaya , L. A. ; Shestopalov , A. M. New, convenient, four-component synthesis of 6-amino-2,4-dihydropyrano[2,3-c]pyrazol-5-carbonitriles and one-pot synthesis of 6′-aminospiro[(3H)-indol-3,4′-pyrano[2,3-c]pyrazol] -(1H)-2-on-5′-carbonitriles . J. Comb. Chem. 2009 , 11 , 914 – 919 ; (b) Gogoi , S. ; Zhao , C. Oranocatalyzed enantioselective synthesis of 6-amino-5-cyanodihydropyrano[2,3-c]pyrazoles . Tetrahedron Lett. 2009 , 50 , 2252 – 2255 ; (c) Vasuki , G. ; Kumaravel , K. Rapid four-component reactions in water: Synthesis of pyranopyrazoles . Tetrahedron Lett. 2008 , 49 , 5636 – 5638 .

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