Efficient Reducing System Based on Iron for Conversion of Nitroarenes to Anilines

REFERENCES

• Kabalka , G. W. ; Varma , R. S. Reduction of nitro and nitroso compounds . In Comprehensive Organic Synthesis, , 1st ed. ; B. M. Trost , and I. Fleming (Eds.); Pergamon Press : Oxford , 1991 ; vol. 8 , p. 363 .
   Google Scholar
• Macleod , C. ; McKiernan , G. J. ; Guthrie , E. J. ; Farrugia , L. J. ; Hamprecht , D. W. ; Macritchie , J. ; Hartley , R. C. Synthesis of 2-substituted benzofurans and indoles using functionalized titanium benzylidene reagents on solid phase . J. Org. Chem. 2003 , 68 , 387 – 401 .
   Web of Science ®Google Scholar
• Ramadas , K. ; Srinivasan , N. Iron-ammonium chloride—A convenient and inexpensive reductant . Synth. Commun. 1992 , 22 , 3189 – 3195 .
   Web of Science ®Google Scholar
• Edwards , J. P. ; Zhi , L. ; Pooley , C. L. F. ; Tegley , C. M. ; West , S. J. ; Wang , M.-W. ; Gottardis , M. M. ; Pathirana , C. ; Schrader , W. T. ; Jones , T. K. Preparation, resolution, and biological evaluation of 5-aryl-1,2-dihydro-5H-chromeno[3,4-f]-quinolines: Potent, orally active, nonsteroidal progesterone receptor agonists . J. Med. Chem. 1998 , 41 , 2779 – 2785 .
   Web of Science ®Google Scholar
• Matthews , J. M. ; Greco , M. N. ; Hecker , L. R. ; Hoekstra , W. J. ; Andrade-Gordon , P. ; de Garavilla , L. ; Demarest , K. T. ; Ericson , E. ; Gunnet , J. W. ; Hageman , W. ; Look , R. ; Moore , J. B. ; Maryanoff , B. E. Synthesis and biological evaluation of novel indoloazepine derivatives as non-peptide vasopressin V2 receptor antagonists . Bioorg. Med. Chem. Lett. 2003 , 13 , 753 – 756 .
   Web of Science ®Google Scholar
• Xiao , Z. P. ; Li , H. Q. ; Shi , L. ; Lv , P. C. ; Song , Z. C. ; Zhu , H. L. Synthesis, evaluation of antiproliferative activity and structure–activity relationship of 3-aryl-1H-quinolin-4-ones . Chem. Med. Chem. 2008 , 3 , 1077 – 1083 .
   Web of Science ®Google Scholar
• Xiao , Z. P. ; Lv , P. C. ; Xu , S. P. ; Zhu , T. T. ; Zhu , H. L. Synthesis, antiproliferative evaluation and structure–activity relationship of 3-arylquinolines . Chem. Med. Chem. 2008 , 3 , 1516 – 1519 .
   Web of Science ®Google Scholar
• Desai , D. G. ; Swami , S. S. ; Dabhade , S. K. ; Ghagare , M. G. FeS-NH4Cl-CH3OH-H2O: An efficient and inexpensive system for reduction of nitroarenes to anilines. Synth. Commun. 2001, 31, 1249–1251.
   Web of Science ®Google Scholar
• Zhu , J. L. ; Wong , H. ; Zhang , Z. G. ; Yin , Z. W. ; Meanwell , N. A. ; Kadow , J. F. ; Wang , T. An effective procedure for the preparation of 3-substituted-4- or 6-azaindoles from ortho-methyl nitro pyridines . Tetrahedron Lett. 2006 , 47 , 5653 – 5656 .
   Web of Science ®Google Scholar
• Patrick , T. B. ; Schield , J. A. ; Kirchner , D. G. Synthesis of fluoroaromatic amines . J. Org. Chem. 1974 , 39 , 1758 – 1761 .
   Web of Science ®Google Scholar
• Van de Graaf , B. ; Hoefnagel , A. J. ; Wepster , B. M. Substituent effects, 7: Microscopic dissociation constants of 4-amino- and 4-(dimethylamino)benzoic acid . J. Org. Chem. 1981 , 46 , 653 – 657 .
   Web of Science ®Google Scholar
• Srinivasa , G. R. ; Abiraj , K. ; Gowda , D. C. Clean and efficient hydrogenative cleavage of azo compounds using polymer-supported formate and zinc . Synth. Commun. 2005 , 35 , 1161 – 1166 .
   Web of Science ®Google Scholar
• Roberts , D. T. ; Little , W. F. ; Bursey , M. Ortho effect in the mass spectra of some carbonylsubstituted phenylferrocenes . J. Am. Chem. Soc. 1967 , 89 , 4917 – 4923 .
   Web of Science ®Google Scholar
• Bersch , H. W. Zur Synthese der Homoisovanillinsäure . Arch. Pharm. 1939 , 277 , 271 – 286 .
   Google Scholar
• Boyer , J. ; Elizey , Jr. , S. Notes—Reduction of the azido group with sodium borohydride . J. Org. Chem. 1958 , 23 , 127 – 129 .
   Web of Science ®Google Scholar
• Ward , R. S. ; Cooks , R. G. ; Williams , D. H. Substituent effects in mass spectrometry. Mass spectra of substituted phenyl benzyl ethers . J. Am. Chem. Soc. 1969 , 91 , 2727 – 2732 .
   Web of Science ®Google Scholar