170
Views
15
CrossRef citations to date
0
Altmetric
Original Articles

Synthesis of 1,2,4-Triazole C-Nucleosides from Hydrazonyl Chlorides and Nitriles

, &
Pages 37-43 | Received 10 Apr 2006, Accepted 19 Jun 2006, Published online: 08 Dec 2006

REFERENCES

  • Naito , Y. , Akahoshi , F. , Takeda , S. , Takada , T. , Kajii , M. , Nishimura , H. , Sugiura , M. , Fukaya , C. and Kagitani , Y. 1996 . Synthesis and pharmacological activity of triazole derivatives inhibiting eosinophilia . J. Med. Chem. , 39 : 3019 – 3029 . [INFOTRIEVE]
  • De Clercq , E. 2004 . Antiviral drugs in current clinical use . J. Clin. Virol. , 30 : 115 – 133 . [INFOTRIEVE] [CROSSREF]
  • Collin , X. , Sauleau , A. and Coulon , J. 2003 . 1,2,4-Triazolo mercapto and aminonitriles as potent antifungal agents . Bioorg. Med. Chem. Lett. , 13 : 2601 – 2605 . [INFOTRIEVE] [CROSSREF] [CSA]
  • Sui , Z. , Guan , J. , Hlasta , D. J. , Macielag , M. J. , Foleno , B. D. , Goldschmidt , R. M. , Loeloff , M. J. , Webb , G. C. and Barrett , J. F. 1998 . SAR studies of diaryltriazoles against bacterial two-component regulatory systems and their antibacterial activities . Bioorg. Med. Chem. Lett. , 8 : 1929 – 1934 . [INFOTRIEVE] [CROSSREF] [CSA]
  • Hester , J.B. , Rudzik , A.D. and Kamdar , B. V. 1971 . 6-Phenyl-4H-s-triazolo[4,3-a][1,4]benzo-diazepines which have central nervous system depressant activity . J. Med. Chem. , 14 : 1078 – 1081 . [INFOTRIEVE] [CROSSREF] [CSA]
  • Heubach , G. , Sachse , B. and Buersteu , H. 1980 . 1,2,4-Triazol derivatives . Ger. Offen. Pat. 2826760, Chem. Abstr. , 92 : 181200h [CSA]
  • Tanaka , G. 1975 . Pesticidal triazolyl diphatic sulfonates . Japan Kokai, 74 95973, Chem. Abstr. , 82 : 156320h [CSA]
  • Goss , P.E. and Strasser-Weippl , K. 2004 . Aromatase inhibitors for chemoprevention . Best Pract. Res. Clin. End. Met. , 18 : 113 – 130 . [CROSSREF] [CSA]
  • Santen , J. R. 2003 . Inhibition of aromatase: insights from recent studies . Steroids , 68 : 559 – 567 . [INFOTRIEVE] [CROSSREF] [CSA]
  • Clemons , M. , Coleman , R.E. and Verma , S. 2004 . Aromatase inhibitors in the adjuvant setting: bringing the gold to a standard? Cancer Treat . Rev. , 30 : 325 – 332 . [CSA]
  • Al-Masoudi , N. A. , Hassan , N. A. , Al-Soud , Y. A. , Schmidt , P. , Gaafer , A.E.-D.M. , Weng , M. , Marino , S. , Schoch , A. , Amer , A. and Jochims , J. C. 1998 . Synthesis of C- and N-nucleosides from 1-aza-2-azoniaellene and 1,3-diaza-2-azoniaaallene salts . Chem. Soc. Perkin Trans. 1 , : 947 – 953 . [CROSSREF] [CSA]
  • Al-Soud , Y. A. , Al-Masoudi , W. A. , El-Halawa , R. A. and Al-Masoudi , N. A. 1999 . Synthesis and antiviral activity of some 1,2,4-triazole C-nucleosides from 1-(chloroalkyl)-1-aza-2-azo-niaallene salts . Nucleosides Nucleotides , 18 : 1985 – 1994 . [INFOTRIEVE] [CSA]
  • Al-Masoudi , I. A. , Al-Soud , Y. A. , Al-Salihi , N. J. and Al-Masoudi , N. A. 2006 . 1,2,4-Triazoles: Synthetic approaches and pharmacological importance . Chem. Heterocycl. Compd. , 11 : 1605 – 1634 . [CSA]
  • Moon , M. W. 1972 . Chlorination of aldehyde and ketone phenylhydrazones . J. Org. Chem. , 37 : 383 – 385 . [CROSSREF] [CSA]
  • Wang , Q. , Jochims , J. C. , Köhlbrandt , S. , Dahlenburg , L. , Al-Talib , M. , Hamed , A. and Ismail , E. A. 1992 . 1,2,4-Triazolium salts from the reaction of 1-aza-2-azaiaaallene salts with nitrile . Synthesis , 710–718 : 710 – 718 . [CROSSREF] [CSA]
  • Al-Soud , Y. A. , Qalalweh , N. A. , Al-Sa’adoni , H. H. and Al-Masoudi , N. A. 2005 . New benzyl-piperazine derivatives bearing mono and bis-dialkyl-substituted 1,2,4-triazoles . Heteroatom Chem. , 16 : 28 – 32 . references therein[CROSSREF] [CSA]
  • Hegarty , A. F. and Kearney , J. A. 1975 . Substituent effects on the solvolysis of α,α′-dichloroazoalkanes. Evidence for open aza-allylic ion intermediates on reaction pathway . J. Org. Chem. , 40 : 3529 – 3536, references therein . [CROSSREF] [CSA]
  • Su , W. , Yang , D. and Li , J. 2005 . Novel process for synthesis of 1,2,4-triazoles: Ytterbium triflate-catalyzed cyclization of hydrazonyl chlorides with nitriles . Synth. Commun. , 35 : 1435 – 1440 . [CROSSREF] [CSA]
  • Paulvannan , K. , Chen , T. and Hale , R. 2000 . An improved synthesis of 1,2,4-triazoles using Ag2CO3 . Tetrahedron , 56 : 8071 – 8076 . [CROSSREF] [CSA]
  • Buzykin , B.I. and Bredikhina , Z. A. 1993 . An approach to 1-aryl-1,2,4-triazoles . Synthesis , 59–61 : 59 – 61 . [CROSSREF] [CSA]
  • Bothner-By , A. A. , Stephensen , R. L. , Lee , J. , Warren , C.D. and Jeanloz , R. W. 1984 . Structure determination of a tetrasaccharide: transient nuclear Overhauser effects in the rotating frame . J. Am. Chem. Soc. , 106 : 811 – 813 . [CROSSREF] [CSA]
  • Wolfrom , M. L. and Thompson , A. 1931 . The reactive form of glucose oxime . J. Am. Chem. Soc. , 53 : 622 – 632 . [CROSSREF] [CSA]
  • Gautun , O.R. and Carlsen , P. H.J. 2001 . Regioselectivity in the thermal rearrangement of unsymmetrical 4-methyl-4H-1,2,4-triazoles to 1-methyl-1H-1,2,4-triazoles . Moecules , 6 : 969 – 978 . [CSA]
  • Al-Masoudi , N. A. , Al-Soud , Y. A. and Al-Masoudi , I. A. 2000 . Thiopyridone nucleosides: Synthesis, antibacterial and antiviral activity of 7-(glycoyl and D-manno-hextitol-1-yl)-2-chloro-4-oxothieno[2,3-a]pyridine-5-carboxylic acids . Sulfur Lett. , 24 : 13 – 22 . [CSA]

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.