[BPy]HSO₄ Acidic Ionic Liquid as a Novel, Efficient, and Environmentally Benign Catalyst for Synthesis of 1,5‐Benzodiazepines under Mild Conditions

References

• Schutz , H. 1982 . Benzodiazepines Heidelberg , , Germany : Springer Verlag .
   Google Scholar
• Landquist , J. K. 1984 . Comprehensive Hetero‐cyclic Chemistry Edited by: Katritzky , A. R. and Rees , C. W. Vol. 1 , 116 Oxford : Pergamon .
   Google Scholar
• Randall , L. O. and Kamal , B. 1973 . Benzodiazepines Edited by: Garattini , S. , Mussini , E. and Randall , L. O. 27 New York : Raven Press . and references cited therein
   Google Scholar
• Baun , J. R. D. , Pallos , F. M. and Baker , D. R. US Patent 3,978,227 . 1976 . Chem. Abstr. 1977, 86, 5498d
   Google Scholar
• Haris , R. C. and Straley , J. M. US Patent 1,537,757 . 1968 . Chem. Abstr., 1970, 73, 100054w
   Google Scholar
• Aversa , M. C. , Ferlazzo , A. , Giannetto , P. and Kohnke , F. H. 1986 . A convenient synthesis of novel [1,2,4]triazolo[4,3‐a][1,5]benzodiazepine derivatives . Synthesis , : 230
   Web of Science ®Google Scholar
• Chimirri , A. , Grasso , S. , Ottana , R. and Romeo Zappala , G. 1990 . Synthesis and stereochemistry of novel [1,2,4]oxadiazolo[4,5‐a][1,5]benzodiazepine derivatives . J. Heterocycl. Chem. , 27 : 371
   Web of Science ®Google Scholar
• Herbert , J. A. L. and Suschitzky , H. J. 1974 . Chem. Soc., Perkin Trans. 1 , : 2657 – 2661 .
   Google Scholar
• Morales , H. R. , Bulbarela , A. and Contreras , R. 1986 . New synthesis of dihydro‐ and tetrahydro‐1,5‐benzodiazepines by reductive condensation of o‐phenylenediamine and ketones in the presence of sodium borohydride . Heterocycles , 24 : 135 – 139 .
   Web of Science ®Google Scholar
• Jung , D. I. , Choi , T. W. , Kim , Y. Y. , Kim , I. S. , Park , Y. M. , Lee , Y. G. and Jung , D. H. 1999 . Synthesis of 1,5‐benzodiazepine derivatives . Synth. Commun. , 29 : 1941 – 1951 .
   Web of Science ®Google Scholar
• Yadav , J. S. , Reddy , B. V. S. , Eshwaraian , B. and Anuradha , K. 2002 . Amberlyst‐15: A novel and recyclable reagent for the synthesis of 1,5‐benzodiazepines in ionic liquids . Green Chem. , 4 : 592 – 594 .
   Web of Science ®Google Scholar
• Curini , M. , Epifano , F. , Marcotullio , M. C. and Rosati , O. 2001 . Ytterbium triflate promoted synthesis of 1,5‐benzodiazepine derivatives . Tetrahedron Lett. , 42 : 3193 – 3195 .
   Web of Science ®Google Scholar
• Balakrishna , M. S. and Kaboundin , B. 2001 . A simple and new method for the synthesis of 1,5‐benzodiazepine derivatives on a solid surface . Tetrahedron Lett. , 42 : 1127 – 1129 .
   Web of Science ®Google Scholar
• Kaboudin , B. and Navaee , K. 2001 . Alumina/phosphorus pentoxide (APP) as an efficient reagent for the synthesis of 1,5‐benzodiazepines under microwave irradiation . Heterocycles , 55 : 1443 – 1446 .
   Web of Science ®Google Scholar
• Pozarentzi , M. , Stephanidou , S. J. and Tsoleridis , C. A. 2002 . An efficient method for the synthesis of 1,5‐benzodiazepine derivatives under microwave irradiation without solvent . Tetrahedron Lett. , 43 : 1755 – 1758 .
   Web of Science ®Google Scholar
• Kidwai , M. and Ruby; Venkataramanan , R. 2004 . A facile synthesis of substituted benzodiazepines using solid support . Chem. Heterocycl. Compd. , 40 : 631 – 634 .
   Google Scholar
• Ma , Y. and Zhang , Y. 2002 . Derivatives of 2,3‐dihydro‐1H‐1,5‐benzodiazepine from o‐nitroanilines and chalcones induced by low‐valent titanium . Synth. Commun. , 32 : 165 – 169 .
   Web of Science ®Google Scholar
• Jarikote , D. V. , Siddique , S. A. , Rajagopal , R. , Daniel , T. , Lahoti , R. J. and Srinivasan , K. V. 2003 . Room temperature ionic liquid promoted synthesis of 1,5‐benzodiazepine derivatives under ambient conditions . Tetrahedron Lett. , 44 : 1835 – 1838 .
   Web of Science ®Google Scholar
• Reddy , B. M. and Sreekanth , P. M. 2003 . An efficient synthesis of 1,5‐benzodiazepine derivatives catalyzed by a solid superacid sulfated zirconia . Tetrahedron Lett. , 44 : 4447 – 4449 .
   Web of Science ®Google Scholar
• Kodomari , M. , Noguchi , T. and Aoyama , T. 2004 . Solvent‐free synthesis of 1,5‐benzothiazepines and benzodiazepines on inorganic supports . Synth. Commun. , 34 : 1783 – 1790 .
   Web of Science ®Google Scholar
• Sabitha , G. , Reddy , G. S. K. K. , Reddy , K. B. , Reddy , N. M. and Yadav , J. S. 2004 . A new, efficient and environmentally benign protocol for the synthesis of 1,5‐benzodiazepines using cerium(III) chloride/sodium iodide supported on silica gel . Adv. Synth. Catal. , 346 : 921 – 923 .
   Web of Science ®Google Scholar
• Rogers , R. D. and Seddon , K. R. 2003 . Ionic liquids—solvents of the future? . Science , 302 : 792 – 793 .
   PubMed Web of Science ®Google Scholar
• Sheldon , R. 2001 . Catalytic reactions in ionic liquids . Chem. Commun. , 1 : 2399 – 2407 . For reviews, see
   Web of Science ®Google Scholar
• Wasserscheid , P. and Keim , W. 2000 . Ionic liquids—new “solutions” for transition metal catalysis . Angew. Chem., Int. Ed. , 39 : 3772 – 3789 .
   PubMed Web of Science ®Google Scholar
• Welton , T. 1999 . Room‐temperature ionic liquids: Solvents for synthesis and catalysis . Chem. Rev. , 99 : 2071 – 2084 .
   PubMed Web of Science ®Google Scholar
• Cole , A. C. , Jensen , J. L. , Ntai , I. , Tran , K. L. T. , Weaver , K. J. , Forbes , D. C. and Davis , J. H. Jr. 2002 . Novel Brønsted acidic ionic liquids and their use as dual solvent‐catalysts . J. Am. Chem. Soc. , 124 : 5962 – 5963 .
   PubMed Web of Science ®Google Scholar
• Yadav , J. S. , Reddt , B. V. S. and Baishya , G. 2003 . Green protocol for conjugate addition of thiols to α,β‐unsaturated ketones using a [Bmim]PF6/H2O system . J. Org. Chem. , 68 : 7098 – 7100 .
   PubMed Web of Science ®Google Scholar
• Chauhan , S. M. S. , Kumar , A. , Srinivas , K. A. , Cole , A. C. , Jensen , J. L. and Nitai , I. 2003 . Oxidation of thiols with molecular oxygen catalyzed by cobalt(II) phthalocyanines in ionic liquid . Chem. Commun. , : 2348 – 2349 .
   PubMed Web of Science ®Google Scholar
• Xu , L. W. , Li , L. , Xia , C. G. , Zhou , S. L. , Li , L. and Li , J. W. 2004 . The first ionic liquids promoted conjugate addition of azide ion to α,β‐unsaturated carbonyl compounds . Tetrahedron Lett. , 45 : 1219 – 1221 .
   Web of Science ®Google Scholar
• Orlov , V. D. , Kolos , N. N. and Abramov , A. F. 1984 . Conformational analysis of aromatic derivatives of 2,3‐dihydro‐1H‐1,5‐benzodiazepines . Khim. Geterotsikl. Soedin. , 12 : 1662 – 1666 . Russ. Chem. Abstra., 1985, 102, 148397e
   Google Scholar
• Orlov , V. D. , Kolos , N. N. , Yaremenko , F. G. and Lavrushin , V. F. 1980 . New aspects of the chemistry 2,3‐dihydro‐1H‐1,5‐benzodiazepines Khim . Geterotsikl. Soedin. , 5 : 697 – 700 . Russ. Chem. Abstra., 1980, 93, 185254x
   Google Scholar
• Palimkar , S. S. , Siddiqui , S. A. , Daniel , T. , Lahoti , R. J. and Srinivasan , K. V. 2003 . Ionic liquid–promoted regiospecific Friedlander annulation: Novel synthesis of quinolines and fused polycyclic quinolines . J. Org. Chem. , 68 : 9371 – 9378 .
   PubMed Web of Science ®Google Scholar
• Fraga , D. J. , Bourahla , K. , Rahmouni , M. , Bazureau , J. P. and Hamelin , J. 2002 . Catalysed esterifications in room temperature ionic liquids with acidic counteranion as recyclable reaction media . Catal. Commun. , 3 : 185 – 190 .
   Web of Science ®Google Scholar
• Singh , V. , Kaur , S. , Sapehiyia , V. , Singh , J. and Kad , G. L. 2005 . Microwave accelerated preparation of [bmim][HSO4] ionic liquid: An acid catalyst for improved synthesis of coumarins . Catal. Commun. , 6 ( 1 ) : 57 – 60 .
   Web of Science ®Google Scholar
• Gui , J. , Cong , X. , Liu , D. , Zhang , X. , Hu , Z. and Sun , Z. 2004 . Novel Brønsted acidic ionic liquid as efficient and reusable catalyst system for esterification . Catal. Commun. , 5 ( 9 ) : 473 – 477 .
   Web of Science ®Google Scholar