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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2011 - Issue 11
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Original Articles

Ecofriendly Synthesis of Novel Benzo-1,2,3-triazol-1-yl-(N-aryl)amidines and Their Conversion to Guanidines

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Pages 1593-1602 | Received 01 Feb 2010, Published online: 20 Apr 2011

REFERENCES

  • Berlinck , R. G. S. ; Burtoloso , A. C. B. ; Kossuga , M. H. The chemistry and biology of organic guanidine derivatives . Natural Prod. Rep. 2008 , 25 , 919 – 954 .
  • Maillard , M. C. ; Perlman , M. E. ; Amitay , O. ; Baxter , D. ; Berlove , D. ; Connaughton , S. ; Fischer , J. B. ; Guo , J. Q. ; Hu , L. Y. ; McBurney , R. N. ; Nagy , P. I. ; Subbarao , K. ; Yost , E. A. ; Zhang , L. ; Durant , G. J. Design, synthesis, and pharmacological evaluation of conformationally constrained analogues of N,N′-diaryl- and N-aryl-N-aralkylguanidines as potent inhibitors of neuronal Na+ channels . J. Med. Chem. 1998 , 41 , 3048 – 3061 .
  • Cesnek , M. ; Holy , A. ; Masojidkova , M. ; Zidek , Z. Synthesis of 9-alkyl and 9-heteroalkyl substituted 2-amino-6-guanidinopurines and their influence on the NO-production in microphages . Bioorg. Med. Chem. 2005 , 13 , 2917 – 2926 .
  • Saczewski , F. ; Balewski , L. Biological activities of guanidine compounds . Exp. Opin. Ther. Patents 2009 , 19 , 1417 – 1448 .
  • Furin , G. G. ; Gatilov , Y. V. ; Bagryanskaya , I. Y. ; Zhuchgov , E. L. Guanidine in the synthesis of perfluoroalkylpyrimidines and perfluoroalkyl-s-triazines . Rus. Chem. Bull. Intl. 2001 , 50 , 476 – 479 .
  • Nie , A. ; Wang , J. ; Huang , Z. Microwave-assisted solution-phase parallel synthesis of 2,4,6-trisubstituted pyrimidines . J. Comb. Chem. 2006 , 8 , 646 – 648 .
  • Chen , J. ; Pattarawarapan , M. ; Zhang , A. J. ; Burgess , K. Solution- and solid-phase syntheses of substituted guanidinocarboxylic acids . J. Comb. Chem. 2000 , 2 , 276 – 281 .
  • Katritzky , A. R. ; Rogovoy , B. V. Recent developments in guanylating agents . Arkivoc 2005 , 4 , 49 – 87 .
  • Castillo-Melenez , J. A. ; Golding , B. T. Optimisation of the synthesis of guanidines from amines via nitroguanidines using 3,5-dimethyl-N-nitro-1H-pyrazole-1-carboxamidine. Synthesis 2004, 1655–1663.
  • Solodenko , W. ; Broker , P. ; Messinger , J. ; Schon , U. ; Kirschning , A. Amidination of amines under microwave conditions using recyclable polymer-bound 1H-pyrazole-1-carboxamidine . Synthesis 2006 , 461 – 466 .
  • Katritzky , A. R. ; Parris , R. L. ; Allin , S. M. ; Steel , P. J. Benzotriazole-1-carboxamidinium tosylate: An alternative method for the conversion of amines to guanidines . Synth. Commun. 1995 , 25 , 1173 – 1186 .
  • Bruker . SABADS, SMART, SAINTPLUS, and SHELXTL ; Bruker AXS Inc. : Madison , WI , 2003 .
  • Sheldrick , G. M. SHELXL-97: Program for Crystal Structure Refinement ; University of Göttingen : Göttingen , Germany , 1997 .
  • Spek , A. L. Single-crystal structure validation with the program PLATON . J. Appl. Cryst. 2003 , 36 , 7 – 13 .

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