Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2010 - Issue 17
444
Views
16
CrossRef citations to date
0
Altmetric
Original Articles

Green and Efficient Protocol for N-Alkylation of Benzotriazole Using Basic Ionic Liquid [Bmim]OH as Catalyst Under Solvent-Free Conditions

, , , &
Pages 2525-2530 | Received 27 Jun 2009, Published online: 05 Aug 2010

REFERENCES

  • Swamy , S. N. ; Basappa ; Sarala , G. ; Priya , B. S. ; Gaonkar , S. L. ; Prasad , J. S. ; Rangappa , K. S. Microwave-assisted synthesis of N-alkylated benzotriazole derivatives: Antimicrobial studies . Bioorg. Med. Chem. Lett. 2006 , 16 , 999 – 1004 .
  • Guida , W. C. ; Mathre , D. J. Phase-transfer alkylation of heterocycles in the presence of 18-crown-6 and potassium tert-butoxide . J. Org. Chem. 1980 , 16 , 3172 – 3176 .
  • Hoffmann , H. ; Pooth , R. Biotransformation von 1H-Benzotriazol und N-1-Alkylbenzotriazolen in vitro . Arch. Pharm. 1982 , 315 , 422 – 428 .
  • Mathias , L. J. ; Burkett , D. N-Alkylation of benzimidazoles and benzotriazole via phase-transfer catalysis . Tetrahedron Lett. 1979 , 20 , 4709 – 4712 .
  • Sukata , K. N-Alkylation of pyrrole, indole, and several other nitrogen heterocycles using potassium hydroxide as a base in the presence of polyethylene glycols or their dialkyl ethers . Bull. Chem. Soc. Jpn. 1983 , 56 , 280 – 284 .
  • Le , Z. G. ; Chen , Z. C. ; Hu , Y. ; Zheng , Q. G. Organic reactions in ionic liquids: An efficient method for the N-alkylation of benzotriazole . J. Chem. Res. 2004 , 2004 , 344 – 346 .
  • Katritzky , A. R. ; Kuzmierkiewicz , W. ; Greenhill , J. V. An improved method for the N-alkylation of benzotriazole and 1,2,4-triazole . Reel. Trav. Chim. Pays-Bas. 1991 , 110 , 369 – 373 .
  • Khalafi-Nezhad , A. ; Zare , A. ; Parhami , A. ; Rad , M. N. S. ; Nejabat , G. R. Highly regioselective N-alkylation of benzotriazole under solvent-free conditions . J. Iran. Chem. Soc. 2007 , 4 , 271 – 278 .
  • Khalafi-Nezhad , A. ; Zare , A. ; Parhami , A. ; Hasaninejad , A. ; Zarea , A. R. M. Quaternary ammonium salts as highly efficient and green alkylating agents for N-alkylation of azaheterocycles under microwave irradiation . J. Iran. Chem. Soc. 2008 , 5 , S40 – S46 .
  • Ballesteros , P. ; Elguero , J. ; Claramunt , R. M. Reactivity of azoles towards benzaldehyde and its dimethylacetal: Synthesis of N,N′-diazolylphenylmethanes . Tetrahedron 1985 , 41 , 5955 – 5963 .
  • Welton , T. Room-temperature ionic liquids: Solvents for synthesis and catalysis . Chem. Rev. 1999 , 99 , 2071 – 2083 .
  • (a) Frizzo , C. P. ; Moreira , D. N. ; Guarda , E. A. ; Fiss , G. F. ; Marzari , M. R. B. ; Zanatta , N. ; Bonacorso , H. G. ; Martins , M. A. P. Ionic liquid as catalyst in the synthesis of N-alkyl trifluoromethyl pyrazoles . Catal. Commun. 2009 , 10 , 1153 – 1156 ; (b) Liang , X. Z. ; Gong , G. Z. ; Wu , H. H. ; Yang , J. G. Highly efficient procedure for the synthesis of biodiesel from soybean oil using chloroaluminate ionic liquid as catalyst . Fuel 2009 , 88 , 603 – 616 ; (c) Saladino , R. ; Crestini , C. ; Crucianelli , M. ; Soldaini , G. ; Cardona , F. ; Goti , A. Ionic liquids in methyltrioxorhenium-catalyzed epoxidation–methanolysis of glycals under homogeneous and heterogeneous conditions . J. Mol. Catal. A: Chem. 2008 , 284 , 108 – 115 ; (d) Haumann , M. ; Jakuttis , M. ; Werner , S. ; Wasserscheid , P. Supported ionic liquid phase (SILP)–catalyzed hydroformylation of 1-butene in a gradient-free loop reactor . J. Catal. 2009 , 263 , 321 – 327 ; (e) Kantevari , S. ; Chary , M. V. ; Das , A. P. R. ; Vuppalapatia , S. V. N. ; Lingaiah , N. Catalysis by an ionic liquid: Highly efficient solvent-free synthesis of aryl-14H-dibenzo[a.j]xanthenes by molten tetrabutylammonium bromide under conventional and microwave heating . Catal. Commun. 2008 , 9 , 1575 – 1578 .
  • Chen , X. ; Li , X. ; Song , H. ; Lü , Y. ; Wang , F. ; Hu , A. Synthesis of a basic imidazolide ionic liquid and its application in catalyzing Knoevenagel condensation . Chin. J. Catal. 2008 , 29 , 957 – 959 .
  • (a) Zhao , Y. W. ; Long , J. X. ; Deng , F. G. ; Liu , X. F. ; Li , Z. ; Xia , C. G. ; Peng , J. J. Catalytic amounts of Brønsted acidic ionic liquids promoted esterification: Study of acidity–activity relationship. Catal. Commun. 2009, 10, 732–736; (b) Qureshi , Z. S. ; Deshmukh , K. M. ; Bhor , M. D. ; Bhanage , B. M. Brønsted acidic ionic liquid as an efficient and reusable catalyst for transesterification of β-ketoesters. Catal. Commun. 2009, 10, 833–837; (c) Hajipour , A. R. ; Rajaei , A. ; Ruoho , A. E. A mild and efficient method for preparation of azides from alcohols using acidic ionic liquid [H-NMP]HSO4 . Tetrahedron Lett. 2009, 50, 708–711; (d) Zhang , H. B. ; Xu , F. ; Zhou , X. H. ; Zhang , G. Y. ; Wang , C. X. A Brønsted acidic ionic liquid as an efficient and reusable catalyst system for esterification. Green Chem. 2007, 9, 1208–1211.
  • Gong , K. ; Fang , D. ; Wang , H. L. ; Liu , Z. L. Basic functionalized ionic liquid–catalyzed one-pot Mannich-type reaction: Three-component synthesis of β-amino carbonyl compounds . Monatsh. Chem. 2007 , 138 , 1195 – 1198 .
  • Ranu , B. C. ; Jana , R. Ionic liquid as catalyst and reaction medium: A simple, efficient, and green procedure for Knoevenagel condensation of aliphatic and aromatic carbonyl compounds using a task-specific basic ionic liquid . Eur. J. Org. Chem. 2006 , 3767 – 3770 .
  • Li , J. ; Sun , H. ; Cai , X. C. ; Dai , L. Y. Application of basic ionic liquid [bmim]OH to Knoevenagel and Perkin reactions . Chin. J. Org. Chem. 2007 , 27 , 1296 – 1299 .
  • Xu , J. M. ; Liu , B. K. ; Wu , W. B. ; Qian , C. ; Wu , Q. ; Lin , X. F. Basic ionic liquid as catalysis and reaction medium: A novel and green protocol for the Markovnikov addition of N-heterocycles to vinyl esters, using a task-specific ionic liquid, [bmIm]OH . J. Org. Chem. 2006 , 71 , 3991 – 3993 .
  • (a) Yang , L. ; Xu , L. W. ; Zhou , W. ; Li , L. ; Xia , C. G. Highly efficient aza-Michael reactions of aromatic amines and N-heterocycles catalyzed by a basic ionic liquid under solvent-free conditions . Tetrahedron Lett. 2006 , 47 , 7723 – 7726 ; (b) Ranu , B. C. ; Banerjee , S. ; Jana , R. Ionic liquid as catalyst and solvent: The remarkable effect of a basic ionic liquid, [Bmim]OH, on Michael addition and alkylation of active methylene compounds . Tetrahedron 2007 , 63 , 776 – 782 ; (c) Xu , J. M. ; Wu , Q. ; Zhang , Q. Y. ; Zhang , F. ; Lin , X. F. A basic ionic liquid as catalyst and reaction medium: A rapid and simple procedure for aza-Michael addition reactions . Eur. J. Org. Chem. 2007 , 2007 , 1798 – 1802 ; (d) Xu , J. M. ; Qian , C. ; Liu , B. K. ; Wu , Q. ; Lin , X. F. A fast and highly efficient protocol for Michael addition of N-heterocycles to α,β-unsaturated compound using basic ionic liquid [Bmim]OH as catalyst and green solvent . Tetrahedron 2007 , 63 , 986 – 990 .
  • Ranu , B. C. ; Adak , L. ; Banerjee , S. Ionic liquid–promoted interrupted Feist–Benary reaction with high diastereoselectivity . Tetrahedron Lett. 2008 , 49 , 4613 – 4617 .
  • (a) Wu , H. ; Zhang , F. R. ; Wan , Y. ; Ye , L. An efficient protocol for Henry reaction using basic ionic liquid [Bmim]OH as catalyst and reaction medium . Lett. Org. Chem. 2008 , 5 , 209 – 211 ; (b) Yadav , L. D. S. ; Rai , A. The first ionic liquid–promoted, three-component coupling strategy for an expeditious synthesis of β-nitrocarbonitriles/thiocyanates . Tetrahedron Lett. 2009 , 50 , 640 – 643 .
  • Le , Z. G. ; Zhong , T. ; Xie , Z. B. ; Xu , J. P. A simple N-substitution of pyrrole and indole using basic ionic liquid [Bmim][OH] as catalyst and green solvent . Heterocycles 2009 , 78 , 2013 – 2020 .
  • Ranu , B. C. ; Banerjee , S. Ionic liquid as catalyst and reaction medium: The dramatic influence of a task-specific ionic liquid, [Bmim]OH, in Michael addition of active methylene compounds to conjugated ketones, carboxylic esters, and nitriles . Org. Lett. 2005 , 7 , 3049 – 3052 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.