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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2011 - Issue 10
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Original Articles

Basic Ionic Liquid as Catalyst for the Efficient and Green Synthesis of 2-Amino-3-nitrobenzonitriles in Ethanol

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Pages 1410-1420 | Received 23 Aug 2009, Published online: 30 Mar 2011

REFERENCES

  • Recent selected examples: (a) Warshakoon , N. C. ; Sheville , J. ; Bhatt , R. T. ; Ji , W. ; Mendez-Andino , J. L. ; Meyers , K. M. ; Kim , N. ; Wos , J. A. ; Mitchell , C. ; Paris , J. L. ; Pinney , B. B. ; Reizes , O. ; Hu , X. E. Design and synthesis of substituted quinolines as novel and selective melanin-concentrating hormone antagonists as anti-obesity agents . Bioorg. Med. Chem. Lett. 2006 , 16 , 5207 – 5211 ; (b) Frazier , K. ; Jazan , E. ; McBride , C. M. ; Pecchi , S. ; Renhowe , P. A. ; Shafer , C. M. ; Taylor , C. ; Bussiere , D. ; He , M. M. ; Jansen , J. M. ; Lapointe , M. ; Ma , S. ; Vora , J. ; Wiesmann , J. Design and structure–activity relationship of heterocyclic analogs of 4-amino-3-benzimidazol-2-ylhydroquinolin-2-one as inhibitors of receptor tyrosine kinases . Bioorg. Med. Chem. Lett. 2006 , 16 , 2247 – 2251 ; (c) Wang , J. Q. ; Gao , M. ; Miller , K. D. ; Sledge , G. W. ; Zheng , Q.-H. Synthesis of [11C]Iressa as a new potential PET cancer imaging agent for epidermal growth factor receptor tyrosine kinase . Bioorg. Med. Chem. Lett. 2006 , 16 , 4102 – 4106 ; (d) Nakamura , H. ; Sasaki , Y. ; Uno , M. ; Yoshikawa , T. ; Asano , T. ; Ban , H. S. ; Fukazawa , H. ; Shibuya , M. ; 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 ; (e) Kaiah , T. ; Lingaiah , B. P. V. ; Narsaiah , B. ; Shireesha , B. ; Kumar , B. A. ; Gururaj , S. ; Pathasarathy , T. ; Sridhar , B. Synthesis and structure–activity relationships of novel pyrimido[1,2-b]indazoles as potential anticancer agents against A-549 cell lines . Bioorg. Med. Chem. Lett. 2007 , 17 , 3445 – 3453 ; (f) Romagnoli , R. ; Baraldi , P. G. ; Carrion , M. D. ; Cara , G. L. ; Preti , D. ; Fruttarolo , F. ; Parani , M. G. ; Tabrizi , M. A. ; Tolomeo , M. ; Grimando , S. ; Cristina , A. D. ; Balazarini , J. ; Hadfield , J. A. ; Brancale , A. ; Hamel , E. Synthesis and biological evaluation of 2- and 3-aminobenzo[b]thiophene derivatives as antimitotic agents and inhibitors of tubulin polymerization . J. Med. Chem. 2007 , 50 , 2273 – 2277 .
  • (a) Olah , G. Friedel–Crafts and Related Reactions ; Wiley Interscience : New York , 1963 ; vols. I–IV ; (b) Pearson , D. E. ; Buehler , C. A. Friedel–Crafts acylation with little or no catalyst. Synthesis 1972, 533–542.
  • Hassan , J. ; Sevignon , M. ; Gozzi , C. ; Schulz , E. ; Lemaire , M. Aryl–aryl bond formation one century after the discovery of the Ullmann reaction . Chem. Rev. 2002 , 102 , 1359 – 1469 .
  • Saito , S. ; Yamamoto , Y. Recent advances in the transition-metal-catalyzed regioselective approaches to polysubstituted benzene derivatives . Chem. Rev. 2000 , 100 , 2901 – 2915 .
  • (a) Xue , D. ; Li , J. ; Zhang , Z.-T. ; Deng , J.-G. Efficient method for the synthesis of polysubstituted benzenes by one-pot tandem reaction of vinyl malononitriles with nitroolefins. J. Org. Chem. 2007, 72, 5443–5445; (b) Milart , P. ; Wilamowski , J. ; Sepiol , J.-J. Synthesis of di- and triamino-l,l′:3′,l″-terphenyls from arylethylidene- and arylidenemalonodinitriles. Tetrahedron 1998, 54, 15643–15656; (c) Wang , X. S. ; Zhang , M. M. ; Li , Q. ; Yao , C. S. ; Tu , S. J. An improved and clean procedure for the synthesis of one-donor poly-acceptors systems containing 2,6-dicyanoamine moiety in aqueous media catalyzed by TEBAC in the presence and absence of K2CO3 . Tetrahedron 2007, 63, 5265–5273.
  • (a) Cammarata , L. ; Kazarian , S. G. ; Salter , P. A. ; Welton , T. Molecular states of water in room temperature ionic liquids . Phys. Chem. Chem. Phys. 2001 , 3 , 5192 – 5200 ; (b) Kamal , A. ; Chouhan , G. Investigations towards the chemoselective thioacetaliztion of carbonyl compounds by using ionic liquid [bmim]Br as a recyclable catalytic medium . Adv. Synth. Catal. 2004 , 346 , 579 – 582 .
  • (a) Raru , 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 ; (b) 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 , 1798 – 1802 ; (c) Tsogoeva , S. B. ; Jagtap , S. B. ; Ardemasova , Z. A. ; Kalikhevich , V. N. Trends in asymmetric Michael reactions catalysed by tripeptides in combination with an achiral additive in different solvents . Eur. J. Org. Chem. 2004 , 4014 – 4019 ; (d) Raru , B. C. ; Banerjee , S. 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 ; (e) 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 ; (f) Raru , 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 ; (g) Xu , J. M. ; Liu , B. K. ; Wu , W. B. ; Qian , C. ; 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 ; (h) Sun , H. ; Zhang , D. ; Wang , F. ; Liu , C. Theoretical study of the mechanism for the Markovnikov addition of imidazole to vinyl acetate catalyzed by the ionic liquid [bmIm]OH . J. Phys. Chem. A. 2007 , 111 , 4535 – 4541 ; (i) 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 ; (j) Yadav , L. D. ; Rai , A. The first ionic liquid-promoted three-component coupling strategy for an expeditious synthesis of b-nitrocarbonitriles/thiocyanates . Tetrahedron Lett. 2009 , 50 , 640 – 643 ; (k) 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 .
  • Raru , B. C. ; Banerjee , S. ; Sowmiah , S. An improved procedure for the three-component synthesis of highly substituted pyridines using ionic liquid . J. Org. Chem. 2007 , 72 , 3152 – 3154 .
  • Yavari , I. ; Kowsari , E. Task-specific basic ionic liquid: A reusable and green catalyst for one-pot synthesis of highly functionalized pyrroles in aqueous media . Synlett. 2008 , 6 , 897 – 899 .
  • Su , W. K. ; Ding , K. ; Chen , Z. W. Cu(OTf)2/Et3N-promoted cyclocondensation of activated a-methylene alkenes and nitroolefins: A novel one-pot synthesis of polysubstituted benzenes . Tetrahedron Lett. 2009 , 50 , 636 – 639 .

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