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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 43, 2013 - Issue 20
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Original Articles

Facile Synthesis of Benzotriazole Derivatives Using Nanoparticles of Organosilane-Based Nitrite Ionic Liquid Immobilized on Silica and Two Room-Temperature Nitrite Ionic Liquids

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Pages 2801-2808 | Received 20 Aug 2012, Published online: 08 Jul 2013

REFERENCES

  • Fu , J. ; Yang , Y. ; Zhang , X.-W. ; Mao , W.-J. ; Zhang , Z.-M. ; Zhu , H.-L. Discovery of 1H-benzo[d][1,2,3]triazol-1-yl 3,4,5-trimethoxybenzoate as a potential antiproliferative agent by inhibiting histone deacetylase . Bioorg. Med. Chem. 2010 , 18 , 8457 .
  • Li , H.-Q. ; Xu , C. ; Li , H.-S. ; Xiao , Z.-P. ; Shi , L. ; Zhu , H.-L. Metronidazole-flavonoid derivatives as anti–Helicobacter pylori agents with potent inhibitory activity against HPE-induced interleukin-8 production by AGS cells . Chem. Med. Chem. 2007 , 2 , 1361 .
  • Biagi , G. ; Giorgi , I. ; Livi , O. ; Scartoni , V. ; Barili , P. L. ; Calderone , V. New 5-substituted-1-(2-hydroxybenzoyl)-benzotriazoles, potassium channel activators, IV . Farmaco 2001 , 56 , 827 .
  • Scapin , G. ; Patel , S. B. ; Becker , J. W. ; Wang , Q. ; Desponts , C. ; Waddleton , D. ; Skorey , K. ; Cromlish , W. ; Bayly , C. ; Therien , M. ; Gauthier , J. Y. ; Li , C.-S. ; Lau , C. K. ; Ramachandran , C. ; Kennedy , B. P. ; Asante-Appiah , E. The structural basis for the selectivity of benzotriazole inhibitors of PTP1B . Biochemistry 2003 , 42 , 11451 .
  • Carta , A. ; Palomba , M. ; Francesco , L. ; Boatto , G. ; Busonera , B. ; Murreddu , M. ; Loddo , R. Synthesis and antiproliferative activity of 3-aryl-2-[1H(2H)-benzotriazol-1(2)-yl] acrylonitriles variously substituted: Part 4 . Farmaco 2004 , 59 , 637 .
  • Xu , L.-Z. ; Jian , F.-F. ; Gao , H.-R. ; Chong , C.-Y. Synthesis, structure and biological activities of S-[a-(4-methoxyphenylcarbonyl)-2-(1,2,4-triazole-1-yl)]ethyl-N,N-dimethyldithiocarbamate . Chin. J. Chem. 2003 , 21 , 1615 .
  • Bushuev , M. B. ; Virovets , A. V. ; Garcia , Y. ; Gieck , C. ; Sheludyakova , L. A. ; Ikorskii , V. N. ; Tremel , W. ; Gutlich , P. ; Lavrenova , L. G. Mononuclear coordination compounds based on a novel chelating triazole ligand: 1-Vinyl-3-acetylamino-1,2,4-triazole . Polyhedron 2002 , 21 , 797 .
  • Perry , C. J. ; Holding , K. ; Tyrrell , E. Simple, novel synthesis for 1-carbamoyl-lH-benzotriazole and some of its analogs . Synth. Commun. 2008 , 38 , 3354 .
  • El-Sabbagh , O. I. ; El-Nabtity , S. M. Synthesis and pharmacological studies for new benzotriazole and dibenzodiazepine derivatives as antipsychotic agents . Bull. Korean Chem. Soc. 2009 , 30 , 1445 .
  • Wan , J. ; Lv , P.-C. ; Tian , N.-N. ; Zhu , H.-L. Facile synthesis of novel benzotriazole derivatives and their antibacterial activity . J. Chem. Sci. 2010 , 122 , 597 .
  • Keskin , S. ; Kayrak-Talay , D. ; Akman , U. ; Hortacsu , Ö. A review of ionic liquids towards supercritical fluid applications . J. Supercrit. Fluids 2007 , 43 , 150 .
  • Zhao , H. ; Yu , N. ; Ding , Y. ; Tan , R. ; Liu , C. ; Yin , D. ; Qiu , H. ; Yin , D. Task-specific basic ionic liquid immobilized on mesoporous silica: Efficient and reusable catalysts for Knoevenagel condensation in aqueous media. Micropor. Mesopor. Mat. 2010, 136, 10.
  • Valizadeh , H. ; Shomali , A. A new nitrite ionic liquid (IL-ONO) as a nitrosonium source for the efficient diazotization of aniline derivatives and in-situ synthesis of azo dyes . Dyes Pigm. 2012 , 92 , 1138 .
  • Valizadeh , H. ; Gholipour , H. [Bmim]NO2/H3BO3 as an effective nitrosonium source for electrophilic aromatic nitrosation under MW-promoted solvent-free conditions . C. R. Chim. 2011 , 14 , 963 .
  • Valizadeh , H. ; Gholipour , H. 1-Butyl-3-methylimidazolium nitrite as a reagent for the efficient N-nitrosation of secondary amines . J. Iran. Chem. Soc. 2011 , 8 , 963 .
  • Valizadeh , H. ; Gholipour , H. ; Mahmoodian , M. Phosphinite ionic liquid (IL-OPPh2) as a recyclable reagent for the efficient synthesis of coumarins under microwave. irradiation conditions . J. Iran. Chem. Soc. 2010 , 8 , 862 .
  • Wang , L. ; Li , H. ; Li , P. Task-specific ionic liquid as base, ligand, and reaction medium for the palladium-catalyzed Heck reaction . Tetrahedron 2009 , 65 , 364 .
  • Wang , H.-X. ; Ji , S.-J. ; Gu , D.-G. Synthesis of N-(α -alkoxyalkyl)benzotriazolescatalyzed by acidic ionic liquid at room temperature . Chin. J. Chem. 2007 , 25 , 1041 .
  • Shi , F. ; Waldo , J. P. ; Chen , Y. ; Larock , R. C. Benzyne click chemistry: Synthesis of benzotriazoles from benzynes and azides . Org. Lett. 2008 , 10 , 2409 .
  • Valizadeh , H. ; Amiri , M. ; Shomali , A. ; Hosseinzadeh , F. Ionic liquid 1-(3-trimethoxysilylpropyl)-3-methylimidazolium nitrite as a new reagent for the efficient diazotization of aniline derivatives and in situ synthesis of azo dyes . J. Iran. Chem. Soc. 2011 , 8 , 495 .
  • Carbon , J. A. Adjacent nitro and guanidino groups, II: The base-catalyzed rearrangement of benzotriazine n-oxides to benzotriazoles . J. Org. Chem. 1961 , 27 , 185 .
  • Zincke , T. ; Helmert , H. I. Zur Constitution der Azimide . J. Prakt. Chem. 1896 , 53 , 91 .
  • Pereira , C. M. P. ; Stefani , H. A. ; Guzenc , K. P. ; Orfaoa , A. T. G. Improved synthesis of benzotriazoles and 1-acylbenzotriazoles by ultrasound irradiation . Lett. Org. Chem. 2007 , 4 , 43 .
  • Valizadeh , H. ; Amiri , M. ; Hoseinzadeh , F. Nanoparticles of organosilane-based nitrite ionic liquid immobilized on silica for the diazotization of aniline derivatives and subsequent synthesis of azo dyes . Dyes Pigm. 2012 , 92 , 1308 .
  • Fries , K. ; Guterbock , H. ; Kuhn , H. Untersuchungen in der Reihe des Azimidobenzols und des N-Methyl-azimidobenzols . Liebigs Ann. Chem. 1934 , 511 , 213 .
  • Plaut , G. W. E. The preparation of 1,5,6-trimethylbenzotriazole and 1-methyl-v-triazole-4,5-dicarboxylic acid . J. Am. Chem. Soc. 1954 , 76 , 5801 .
  • Wiley , R. H. ; Hussung , K. F. Halogenated benzotriazoles . J. Am. Chem. Soc. 1957 , 79 , 4395 .
  • Kopanska , K. ; Najda , A. ; Zebrowska , J. ; Chomicz , L. ; Piekarczyk , J. ; Myjakd , P. ; Bretner , M. Synthesis and activity of 1H-benzimidazole and 1H-benzotriazole derivatives as inhibitors of Acanthamoeba castellanii . Bioorg. Med. Chem. 2004 , 12 , 2617 .
  • Charushin , V. N. ; Kotovskaya , S. K. ; Romanova , S. A. ; Chupakhin , O. N. ; Tomilov , Y. V. ; Nefedov , O. M. 4,5-Difluoro-1,2-dehydrobenzene: Generation and cycloaddition reactions . Mendeleev Commun. 2005 , 15 , 45 .

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