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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2011 - Issue 15
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Original Articles

Preparation of Amidines from Amidoximes via Transfer Hydrogenation

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Pages 2195-2199 | Received 28 Sep 2009, Published online: 25 May 2011

REFERENCES

  • (a) Boyd , G, V. The Chemistry of Amidine and Imidates ; S. Patai , Z. Rappoportrt (Eds.); Wiley : Chichester , UK , 1991 , vol. 2 , pp. 367 – 424 ; (b) Greenhill, J. V.; Lue, P. Amidines and guanidines in medicinal chemistry. Prog. Med. Chem. 1993, 30, 203–326.
  • Sielecki , T. M. ; Liu , J. ; Mousa , S. A. ; Racanelli , A. L. ; Hausner , E. A. ; Wexler , R. R. ; Olson , R. E. Synthesis and pharmacology of modified amidine isoxazoline glycoprotein IIb/IIIa receptor antagonists . Bioorg. Med. Chem. Lett. 2001 , 11 , 2201 – 2204 .
  • Stephens , C. E. ; Tanious , E. ; Kim , S. ; Wilson , D. W. ; Schell , W. A. ; Perfect , J. R. ; Frazblau , S. G. ; Boykin , D. W. Diguanidino and “reversed” diamidino 2,5-diarylfurans as antimicrobial agents . J. Med. Chem. 2001 , 44 , 1741 – 1748 .
  • Collins , J. L. ; Shearer , B. G. ; Oplinger , J. A. ; Lee , S. ; Garvey , E. P. ; Salter , B. G. ; Oplinger , J. A. ; Lee , S. ; Garvey , E. P. ; Salter , M.; Dufry. ; Burnette , T. C. ; Furtine , E. S. N-Phenylamidines as selective inhibitors of human neuronal nitric oxide synthase: Structure–activity studies and demonstration of in vivo activity. J. Med. Chem. 1998, 41, 2858–2871.
  • Nakamura , H. ; Sasaki , Y. ; Uno , M. ; Yoshikawa , T. ; Ansano , T. ; Ban , H. S. ; Fukazawa , S. ; Uehara , Y. Synthesis and biological evaluation of benzamides and benzamidines as selective inhibitors of VEGFR tyrosine kinases . Bioorg. Med. Chem. Lett. 2006 , 16 , 5127 – 5131 .
  • Roger , R. ; Nielson , D. G. The chemistry of imidate . Chem. Rev. 1961 , 61 , 179 – 211 .
  • (a) Bredereck , H. ; Gompper , R. ; Seiz , H. Formamid-reaktionen, IX: Umsetzungen des thioformamids mit halogenverbindungen . Chem. Ber. 1957 , 90 , 1837 – 1843 ; (b) Lage , U. W. ; Schafer , B. ; Baucke , D. ; Buschamann , E. ; Mack , H. A new mild method for the synthesis of amidines . Tetrahedron Lett. 1999 , 40 , 7067 – 7070 .
  • Garigipati , R. S. An efficient conversion of nitriles to amidines . Tetrahedron lett. 1990 , 31 , 1969 – 1972 .
  • (a) Moormann , A. F. ; Wang , J. L. ; Palmquist , K. E. ; Promo , M. A. ; Snyder , J. S. ; Scholten , J. A. ; Mass , M. A. ; Snyder , J. S. ; Schlten , J. A. ; Webber , R. K. 3-Methyl-4H-[1,2,4]-oxadiazol-5-one: A versatile synthon for protecting monosubstituted acetamidines . Tetrahedron 2004 , 60 , 10907 – 10914 ; (b) Sendzik , M. ; Hui , H. C. Environmentally friendly and efficient: Iron-mediated reduction of 3-methyl-5-aryl-1,2,4-oxadiazoles to benzamidines . Tetrahedron Lett. 2003 , 44 , 8697 – 8700 .
  • Udeo , E. ; Lang , W. ; Schiffer , B. ; Baucke , D. ; Buschmann , E. ; Mack , H. A new mild method for the synthesis of amidines. Tetrahedron Lett. 1999 , 40 , 7067 – 7071 .
  • (a) Eloy , L. ; Lenaers , R. The chemistry of amidoximes and related compounds . Chem. Rev. 1962 , 62 , 155 – 183 ; (b) Judkins , B. D. ; Allens , D. G.; Cook. T. A. ; Evans , B. ; Sardharwala , T. E. A versatile synthesis of amidines from nitriles via amidoximes . Synth. Commum. 1996 , 26 ( 23 ), 4351 – 4367 ; (c) Denar , J. M. ; Wang , V. R. ; Rice , K. D. ; Gangloff , A. R. ; Kiuo , F. Y. L. ; Newcomb , W. S. ; Putnam , D. ; Wong , M. U. Monocharged inhibitors of mast cell tryptase derived from potent and selective dibasic inhibitors . Bioorg. Med. Chem. Lett. 2001 , 11 , 2325 – 2330 ; (d) Lepore , S. D. ; Schachi , A. L. ; Wiley , M. R. Preparation of 2-hydroxybenzamidines from 3-aminobenzisoxazoles . Tetrahedron Lett. 2003 , 43 , 8777 – 8779 .
  • Carrington , H. C. 1:2 Dihydro2:2-dimethyl quinazoline . J. Chem. Soc. 1955 , 3 , 2527 – 2528 .
  • Zierk , T. ; Mack , H. WO Patent 0061574, 2000 . Chem. Abstr. 2000 , 133 , 282087 .
  • Roussel , B. ; Bradley , M. ; Matthews , I. ; Kane , P. A linker for amidines in solid-phase synthesis . Tetrahedron Lett. 1997 , 38 , 4861 – 4864 .
  • Cesar , J. ; Nadrah , K. ; Dolenc , M. S. Solid-phase synthesis of amidines by the reduction of amidoximes . Tetrahedron Lett. 2004 , 45 , 7445 – 7449 .
  • Nadrah , K. ; Dolenc , M. S. Preparation of amidines by amidoxine reduction with potassium formate . Synlett 2007 , 18 , 1257 – 1258 .
  • Anbazhagan , M. ; Boykin , D. W. ; Stephens , C. E. Direct conversion of amidoxine to amidine via transfer hydrogenation . Synthesis 2003 , 16 , 2467 – 2469 .
  • Mandal , P. K. ; McMurray , J. S. Pd-C-induced catalytic transfer hydrogenation with triethyl silane . J. Org. Chem. 2007 , 72 , 6599 – 6601 .
  • Mahadeven , A. ; Sard , H. ; Gonzalez , M. ; McKew , J. C. A general method for C3 reductive alkylation of indoles . Tetrahedron Lett. 2003 , 44 , 4589 – 4591 .
  • Mirza-Aghayan , M. ; Boukherroub , R. ; Rahimifard , M. A simple and efficient hydrogenation of benzyl alcohols to methylene compounds using triethylsilane and a palladium catalyst . Tetrahedron Lett. 2009 , 50 , 5930 – 5932 .

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