Studies on the Reduction of the Nitro Group in 4-Nitroindazoles by Anhydrous SnCl₂ in Different Alcohols

REFERENCES

• Stéphane , U. ; Falguières , A. ; Guy , A. ; Ferroud , C. Ultrasonically activated reduction of substituted nitrobenzenes to corresponding N-arylhydroxylamines . Tetrahedron Lett. 2005 , 46 , 5913 – 5917 .
   Web of Science ®Google Scholar
• Kabalka , G. W. ; Verma , R. S. Reduction of nitro and nitroso compounds ; In Comprehensive Organic Synthesis ; B. M. Trost and E. Fleming (Eds.); Pergamon Press : Oxford , 1991 ; Vol. 8 , pp. 363 – 379 .
   Google Scholar
• Moglie , Y. ; Vitale , C. ; Radivoy , G. Synthesis of azo compounds by nanosized iron-promoted reductive coupling of aromatic nitro compounds . Tetrahedron Lett. 2008 , 49 , 1828 – 1831 .
   Web of Science ®Google Scholar
• (a) Martin , E. L. o-Phenylenediamine . Org. Synth. Coll. 1943 , 2 , 501 ; (b) Shundberg , R. ; Pitts , W. Synthesis of cycloprop[c]indol-5-ones from 4-diazo-3-[n-(2-propenyl)amido]cyclohexadien-1-ones: Exploration of copper(I) and copper(II) complexes as catalysts . J. Org. Chem. 1991 , 56 , 3048 – 3054 .
   Google Scholar
• (a) Hartman , W. W. ; Dickey , J. B. ; Stampfli , J. G. 2,6-Dibromoquinone-4-chloroimide . Org. Synth. Coll. 1943 , 2 , 175 ; (b) Clarke , H. T. ; Hartman , W. W. Phloroglucinol . Org. Synth. Coll. 1941 , 1 , 455 .
   Google Scholar
• Ponticello , G. S. ; Baldwin , J. J. Useful synthesis of 4-substituted indoles . J. Org. Chem. 1979 , 44 , 4003 – 4005 .
   Web of Science ®Google Scholar
• Somei , M. ; Inoue , S. ; Tokutake , S. ; Yamada , F. ; Kaneko , C. The chemistry of indoles, XIII: Syntheses of substituted indoles carrying an amino, nitro, methoxycarbonyl, or benzyloxy group at the 4-position and their 1-hydroxy derivatives . Chem. Pharm. Bull. 1981 , 29 , 726 – 738 .
   Web of Science ®Google Scholar
• Batcho , A. D. ; Leimgruber , W. Indoles from 2-methylnitrobenzenes by condensation with formamide acetals followed by reduction: 4-Benzyloxyindole . Org. Synth. Coll. 1990 , 7 , 34 .
   Google Scholar
• (a) Rylander , P. N. Catalytic Hydrogenation Over Platinum Metals ; Academic Press ; New York , 1967 ; pp. 168 – 202 ; (b) Siegel , S. ; In Comprehensive Organic Synthesis ; B. M. Trost , and I. Flemming (Eds.); Pergamon Press : Oxford , 1991 ; vol. 8 , pp. 418 – 442 ; (c) Hudlicky , M. Reductions in Organic Chemistry ; Ellis Horwood Ltd : Chichester , 1984 ; pp. 1 – 13 ; (d) Smith , G. V. ; Nothesiz , F. Heterogeneous Catalysis in Organic Chemistry ; Academic Press : New York , 1999 ; pp. 71 – 79 .
   Google Scholar
• Bouissane , L. ; El Kazzouli , S. ; Leger , J. M. ; Jarry , C. ; Rakib , E. M. ; Khouili , M. ; Guillaumet , G. New and efficient synthesis of bi- and trisubstituted indazoles . Tetrahedron 2005 , 61 , 8218 – 8225 .
   Web of Science ®Google Scholar
• Bouissane , L. ; El Kazzouli , S. ; Léonce , S. ; Pfeiffer , P. ; Rakib , E. M ; Khouili , M. Guillaumet , G. Synthesis and biological evaluation of N-(7-indazolyl)benzenesulfonamide derivatives as potent cell cycle inhibitors . Bioorg. Med. Chem. 2006 , 14 , 1078 – 1088 .
   PubMed Web of Science ®Google Scholar
• Noelting , E. Ueber bildung von indazolen aus nitrirten orthomethyllirten aminen. Ber. 1904, 37, 2556–2597.
   Google Scholar
• Terrier , F. Nucleophilic Aromatic Displacement: The Influence of the Nitro Group ; VCH : New York , 1991 .
   Google Scholar
• (a) Makosza , M. ; Wojciechowski , K. Nucleophilic aromatic substitution of hydrogen as a tool for the synthesis of indole and quinoline derivatives . Heterocycles 2001 , 54 , 445 – 474 ; (b) Makosza , M. ; Stalewski , J. The vicarious nucleophilic substitution of hydrogen and related reactions in nitrobenzoxazoles . Tetrahedron 1995 , 51 , 7277 – 7286 ; (c) Makosza , M. ; Sienkiewiez , K. Hydroxylation of nitroarenes with alkyl hydroperoxide anions via vicarious nucleophilic substitution of hydrogen . J. Org. Chem. 1998 , 63 , 4199 – 4209 .
   Web of Science ®Google Scholar
• Chupakhin , O. N. ; Charushin , V. N. ; van der Plas , H. C. Nucleophilic Aromatic Substitution of Hydrogen ; Academic Press : San Diego , 1994 .
   Google Scholar