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Silicotungstic Acid in Organic Synthesis: Synthesis of 1, 5-Benzodiazepines and β-Amino Carbonyl Compounds

Author Affiliations

  • 1Department of Chemistry, Dr. B. R. Ambedkar National Institute of Technology, Jalandhar - 144011, INDIA

Res.J.chem.sci., Volume 3, Issue (4), Pages 59-64, April,18 (2013)

Abstract

An efficient methodology, employing silicotungstic acid (STA) as catalyst leads to synthesis of 1, 5-benzodiazepines and amino carbonyl compounds, employing condensation reaction of o-phenylenediamine with ketones and one pot three component Mannich reaction at room temperature under solvent free conditions in good to excellent yields. The synthetic protocol offers a novel and improved modification for the synthesis of 1, 5-benzodiazepines and -amino carbonyl compounds in terms of mild reaction conditions and clean reaction profiles, high yields and a simple workup procedure. They are characterised by IR and H NMR spectroscopy.

References

  1. Smalley R.K., In Comprehensive Organic Chemistry; Oxford:Pergamon, 1979
  2. Landquist J.K., In Comprehensive Heterocyclic Chemistry; Oxford:Pergamon, 1984
  3. Essaber M. Baouid A. Hasnaoui A. Benharref A. and Lavergne J.P., Synthesis of New Tri- and Tetraheterocyclic Systems: 1,3-Dipolar Cycloaddition of Nitrilimines on 2,7-Dimethyl-4-Phenyl-3H-1,5-Benzodiazepine, Synth. Commun., 28, 4097-4104 (1998)
  4. .Bennamane N. Kaoua R. Hammal L. and Nedjar-Kolli B., Synthesis of new amino-1,5-benzodiazepine and benzotriazole derivatives from dimedone, Org. Commun., , 62-68 (2008)
  5. Boudina A. Baouid A. Hasnaoui A. and Essaber M., Synthesis of New Tetraheterocyclic Systems by the Mixed Condensation Reactions on [1,2,4]Triazolo[4,3a][1,5]benzodiazepines, Synth. Commun., 36, 573-579 (2006)
  6. Xu J. X. Wu H. T. and Jin S., Cycloaddition of benzoheteroazepine II Reactions and conformations of cycloadducts on 1, 5-benzothiazepines and 1,5-benzodiazepines with nitrile imine and nitrile oxides, Chin. J. Chem. 17, 84-91 (1999)
  7. Nabih K. Baouid A. Hasnaoui A. and Kenz A., Highly Regio- and Diastereoselective 1,3-Dipolar Cycloaddition of Nitrile Oxides to 2,4-Dimethyl-3H-1,5-Benzodiazepines: Synthesis of Bis[1,2,4Oxadiazolo][1,5]Benzodiazepine Derivatives, Synth. Commun. 34, 3565-3572 (2004)
  8. Reddy K. V. V. Rao P. S. and Ashok D., A Facile Synthesis of 2-Benzoyl-6-Hydroxy-3-Methyl-5-(2-Substituted-2,3-Dihydro-1-1,5-Benzodiazepin-4-YLBenzo[]Furans, Synth. Commun., 30, 1825-1836 (2000)
  9. Stahlofen P. and Ried W., Über heterocyclische Siebenringsysteme, V. Umsetzung von -phenylendiamin mit -ungesättigten carbonylverbindungen, Chem. Ber.90, 815-824 (1957)
  10. Ried W. and Torinus E., Über heterocyclische siebenringsysteme, X. Synthesen kondensierter 5-, 7- und 8-gliedriger Heterocyclen mit 2 Stickstoffatomen, Chem. Ber. 92, 2902-2916 (1959)
  11. Kodomari M. Noguchi T. and Aoyama T., SolventFree Synthesis of 1, 5Benzothiazepines and Benzodiazepines on Inorganic Supports, Synth. Commun. 34, 1783-1790 (2004)
  12. Herbert J.A. and Suschitzky H., Syntheses of heterocyclic compounds. Part XXIX. Substituted 2,3-dihydro-1H-1,5-benzodiazepines, J. Chem. Soc., Perkin Trans. 1, 2657-2665 (1974)
  13. Morales H.R. Bulbarela A. and Contreras R., 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 (1986)
  14. Chari M. A. and Syamasunder K., Polymer (PVP) supported ferric chloride: an efficient and recyclable heterogeneous catalyst for high yield synthesis of 1,5-benzodiazepine derivatives under solvent free conditions and microwave irradiation, Catal. Commun., 67-70 2005)
  15. Balakrishna M. S. and Kaboudin B., A simple and new method for the synthesis of 1,5-benzodiazepine derivatives on a solid surface, Tetrahedron Lett., 42, 1127-1129 (2001)
  16. Kaboadin B. and Navaee K., Alumina/phosphorus pentoxide (APP) as an efficient reagent for the synthesis of 1,5-benzodiazepines under microwave irradiation,Heterocycles, 55, 1443-1446 (2001)
  17. Kuo C. W. More S. V. and Yao C. F., NBS as an efficient catalyst for the synthesis of 1,5-benzodiazepine derivatives under mild conditions, Tetrahedron Lett. 47, 8523-8528 2006)
  18. Yadav J.S. Reddy B.V.S. Praveen Kumar S. and Nagaiah K., Indium(III) bromide: A novel and efficient reagent for the rapid synthesis of 1,5-benzodiazepines under solvent-free conditions, Synthesis, 480-484 (2005)
  19. De S. K. and Gibbs R. A., Scandium(III) triflate as an efficient and reusable catalyst for synthesis of 1,5-benzodiazepine derivatives, Tetrahedron Lett., 46, 1811-1813 (2005)
  20. Heravi M. M. Derikvand F. Ranjbar, L. and Oskooie H. A., Kaolin: A recyclable catalyst for the synthesis of 1,5-benzodiazepines, Heteroatom Chemistry, 19, 215-217 2008)
  21. Gao S. T. Liu W. H. Ma J. J. Wang C. and Liang Q., NbCl as an Efficient Catalyst for the Synthesis of 1,5-Benzodiazepine Derivatives, Synth. Commun., 39, 3278-3284 (2009)
  22. Arend M. Westermann B. and Risch N., Modern Variants of the Mannich Reaction, Angew. Chem. Int. Ed., 37, 1044-1070 (1998)
  23. Marques M. M. B., Catalytic Enantioselective Cross-Mannich Reaction of Aldehydes, Angew Chem. Int. Ed., 45348-352 (2006)
  24. Muller R. Goesmann H. and Waldmann H., Phthaloylamino Acids as Chiral Auxiliaries in Asymmetric Mannich-Type Reactions, Angew Chem. Int. Ed., 38, 184-187 (1999)
  25. Bohme H. and Haake M., Advances in Organic Chemistry; New York:John Wiley and Sons, 1976
  26. (a) Dziedzic P. Ibrahem I. and Cordova A., Direct catalytic asymmetric three-component Mannich reactions with dihydroxyacetone: enantioselective synthesis of amino sugar derivatives, Tetrahedron lett., 49, 803-807 (2008) (b) Hayashi Y. Urushima T. Aratake S. Okano T. and Obi K., Organic Solvent-Free, Enantio- and Diastereoselective, Direct Mannich Reaction in the Presence of Water ,Org. Lett., 10, 21-24 (2008) (c) Khan A.T. Pravin T. and Choudhary L.H., Bromodimethylsulfonium Bromide Catalyzed Three-Component Mannich-Type Reactions, Eur. J. Org. Chem., 834-839 (2008) (d) Bigdeli M.A. Nemati F. and Mahdavina G.H., HClO–SiO catalyzed stereoselective synthesis of -amino ketones via a direct Mannich-type reaction Tetrahedron Lett., 48, 6801-6804 2007) (e) Guo Q. X. Liu H. Guo C. Luo S. W. Gu Y. and Gong L. Z., Chiral Brønsted Acid-Catalyzed Direct Asymmetric Mannich Reaction, J. Am. Chem. Soc., 129, 3790-3791 (2007)(f) Wang R. Li B. G. Huang T. K. Shi L. and Lu X. X., NbCl-Catalyzed one-pot Mannich-type reaction: three component synthesis of -amino carbonyl compounds, Tetrahedron Lett., 48, 2071-2073 (2007) (g) Wu H. Shen L. Y. Fan Y. Zhang P. Chen C. F. and Wang W. X., Stereoselective synthesis of -amino ketones via direct Mannich-type reaction catalyzed with silica sulfuric acid, Tetrahedron, 632404-2408 (2007) (h) Cheng L. Wu X. and Lu Y., Direct asymmetric three-component organocatalytic anti-selective Mannich reactions in a purely aqueous system, Org. Biomol. Chem., , 1018-1020 (2007)
  27. Cordova A. and Rios R., In Amino Group Chemistry from Synthesis to the Life Sciences; Wiley-VCH: Weinheim, 2008
  28. (a)Rajput J. Singh B. And Singal K. K., One-pot synthesis of pyrrolo-[3,4-d]isoxazoline-4,6-diones via nitrile oxides, Chemistry of Heterocyclic Compounds, 45, 361-364 (2009) (b) Kaur J. Singh B. and Singal K. K., Huisgen reaction of nitrile oxides and nitrile imines leading to isoxazoline and pyrazole-4,6-diones, Chemistry of Heterocyclic Compounds, 42, 818-822 (2006)
  29. (a) Misono M. Ono L. Koyano G. and Aoshima A., Heteropolyacids. Versatile green catalysts usable in a variety of reaction media, Pure Appl. Chem., 72, 1305-1311 2000) (b) Pope M. T. and Mullar A., Polyoxometalates: From Platonic Solids to Anti-RetroViral ActiVity; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1994
  30. (a) Heravi M. M. Bakhtiari K. H. and Bamoharram F. F., An efficient and chemoselective synthesis of acylals from aromatic aldehydes and their regeneration, catalyzed by 12-molybdophosphoric acid, Catal. Commun., , 499-501 2006) (b) Heravi M. M. Bamoharram F. F. Rajabzadeh G. Seifi N. and Khatami M., Preyssler heteropolyacid [NaP3011014 , as a new, green and recyclable catalyst for the synthesis of [1,2,4]triazino[4,3-b][1,2,4,5]tetrazines, J. Mol. Catal. A: Chem., 259, 213-217 (2006)
  31. Heravi M. M. Bakhtiari K. and Bamoharram F. F., 12-Molybdophosphoric acid: A recyclable catalyst for the synthesis of Biginelli-type 3,4-dihydropyrimidine-2(1H)-ones, Catal.Commun., , 373-376 (2006)