Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2011 - Issue 5
223
Views
15
CrossRef citations to date
0
Altmetric
Original Articles

Cellulose Sulfuric Acid: Novel and Efficient Biodegradable and Recyclable Acid Catalyst for the Solid-State Synthesis of Thiadiazolo Benzimidazoles

, , , , &
Pages 662-669 | Received 04 Nov 2009, Published online: 31 Jan 2011

REFERENCES

  • (a) Zarriumayeh , H. ; Zimmerman , D. M. ; Cantrell , B. E. ; Schober , D. A. ; Bruns , R. B. ; Gackenheimer , S. L. ; Ornstein , P. L. ; Hipskind , P. A. ; Brittan , T. C. ; Gchlert , D. R. Structure–activity relationship of a series of diaminoalkyl substituted benzimidazole as neuropeptide Y Y1 receptor antagonists . Bioorg. Med. Chem. Lett. 1999 , 9 , 647 ; (b) Terzioglu , N. ; Rijin , R. M. V. ; Bakker , R. A. ; Desch , I. J. ; Lecurs , R. Synthesis and structure–activity relationships of indole and benzimidazole piperazines as histamine H4 receptor antagonists . Bioorg. Med. Chem. Lett. 2004 , 14 , 5251 .
  • (a) Erhardt , P. W. In search of the digitalis replacement . J. Med. Chem. 1987 , 30 , 231 ; (b) Ries , U. J. ; Mihm , G. ; Narr , B. ; Hasselbach , K. M. ; Wittenben , H. ; Entzeroth , M. ; Meel , J. C. A. V. ; Wienen , W. ; Hauel , N. H. 6-Substituted benzimidazoles as new nonpeptide angiotensin II receptor antagonists: Synthesis, biological activity, and structure–activity relationships . J. Med. Chem. 1993 , 36 , 4040 ; (c) Mann , J. ; Baron , A. ; Opoku–Boahen , Y. ; Johansson , E. ; Parkinson , G. ; Kelland , L. R. ; Neidle , S. A new class of symmetric bisbenzimidazole-based DNA minor groove binding agents showing antitumor activity . J. Med. Chem. 2001 , 44 , 138 ; (d) Song , X. ; Vig , B. S. ; Lorenzi , P. L. ; Darach , J. C. ; Townsend , L. B. ; Amiadon , G. L. Amino acid ester prodrugs of the antiviral agent 2-bromo-5,6-dichloro-1-(β-d-ribofuranosyl) benzimidazole as potential substrates of hPEPT1 transporter . J. Med. Chem. 2005 , 48 , 1274 .
  • Zarrinmayeh , H. ; Nunes , A. M. ; Ornstein , P. L. ; Zimmerman , A. ; Gackenheimer , S. L. ; Bruns , R. F. ; Hipskind , A. ; Britton , T. C. ; Cantrell , B. E. ; Gehlert , D. R. Synthesis and evaluation of a series of novel 2-[(4-chlorophenoxy)methyl]-benzimidazoles as selective neuropeptide Y Y1 receptor antagonists . J. Med. Chem. 1998 , 41 , 2709 .
  • Zhao , J. ; Arnaiz , D. ; Griedel , B. ; Sakata , B. ; Dallas , J. ; Whitlow , M. ; Trinh , L. ; Post , J. ; Liang , A. ; Morrissey , M. ; Shaw , K. Design, synthesis, and in vitro biological activity of benzimidazole-based factor Xa inhibitors . Bioorg. Med. Chem. Lett. 2000 , 10 , 963 – 966 .
  • Denny , W. A. ; Rewcastle , G. W. ; Bagley , B. C. Potential antitumor agents, 59: Structure–activity relationships for 2-phenylbenzimidazole-4-carboxamides, a new class of minimal DNA-intercalating agents which may not act via topoisomerase II . J. Med. Chem. 1990 , 33 , 814 – 819 .
  • Forseca , T. ; Gigante , B. ; Gilchrist , T. L. A short synthesis of phenanthro[2,3-d]imidazoles from dehydroabietic acid: Application of the methodology as a convenient route to benzimidazoles . Tetrahedron 2001 , 57 , 1793 – 1799 .
  • (a) Bai , Y. ; Lu , J. ; Shi , Z. ; Yang , B. Synthesis of 2,15-hexadecanedione as a precursor of muscone. Synlett 2001, 544–546; (b) Hasegawa , E. ; Yoneoka , A. ; Suzuki , K. ; Kato , T. ; Kitazume , T. ; Yangi , K. Reductive transformation of α,β-epoxy ketones and other compounds promoted through photoinduced electron-transfer processes with 1,3-dimethyl-2-phenylbenzimidazoline (DMPBI). Tetrahedron 1999, 55, 12957–12968.
  • Hisano , T. ; Ichikawa , M. ; Tsumoto , K. ; Tasaki , M. Synthesis of benzoxazoles, benzothiazoles, and benzimidazoles and evaluation of their antifungal, insecticidal, and herbicidal activities . Chem. Pharm. Bull. 1982 , 30 , 2996 .
  • Tidwell , R. R. ; Geratz , J. D. ; Dann , O. ; Volz , G. ; Zeh , D. ; Loewe , H. Diarylamidine derivatives with one or both of the aryl moieties consisting of an indole or indole-like ring: Inhibitors of arginine-specific esteroproteases . J. Med. Chem. 1978 , 21 , 613 .
  • Sun , Q. ; Yan , B. Single bead IR monitoring of a novel benzimidazole synthesis . Bioorg. Med. Chem. Lett. 1998 , 8 , 361 – 364 .
  • (a) Pertry , R. J. ; Wilson , B. D. A novel palladium-catalyzed synthesis of 2-arylbenzimidazoles . J. Org. Chem. 1993 , 58 , 7016 – 7021 ; (b) Anastasiou , D. ; Campi , E. M. ; Chaouk , H. ; Jackson , W. R. Synthesis of benzimidazoles containing a fused alicyclic ring by rhodium-catalysed hydroformylation of N-alkenyl-1,2-diaminobenzenes . Tetrahedron 1992 , 48 , 7467 – 7478 ; (c) Brain , C. T. ; Brunton , S. A. An intramolecular palladium-catalysed aryl amination reaction to produce benzimidazoles . Tetrahedron Lett. 2002 , 43 , 1893 – 1895 .
  • (a) Wu , Z. ; Rea , P. ; Wickam , G. “One-pot” nitro reduction–cyclisation solid-phase route to benzimidazoles . Tetrahedron Lett. 2000 , 41 , 9871 – 9874 , and references cited therein ; (b) Mazurov , A. Traceless synthesis of benzimidazoles on solid support . Bioorg. Med. Chem. Lett. 2000 , 10 , 67 – 70 .
  • Chakrabarty , M. ; Karmakar , S. ; Mukherji , A. ; Arima , S. ; Harigaya , Y. Application of sulfamic acid as an eco-friendly catalyst in an expedient synthesis of benzimidazoles . Heterocycles 2006 , 68 , 967 .
  • Gogoi , P. ; Konwar , D. An efficient and one-pot synthesis of imidazolines and benzimidazoles via anaerobic oxidation of carbon–nitrogen bonds in water . Tetrahedron Lett. 2006 , 47 , 79 .
  • Lee , K. J. ; Janda , K. D. Traceless solid-phase synthesis of 5-benzoylbenzimidazoles . Can. J. Chem. 2001 , 79 , 1556 .
  • Lin , S. ; Yang , L. A simple and efficient procedure for the synthesis of benzimidazoles using air as the oxidant . Tetrahedron Lett. 2005 , 46 , 4315 .
  • Beaulieu , P. L. ; Hache , B. , Von Moos , E. A practical oxone-mediated, high-throughput, solution-phase synthesis of benzimidazoles from 1,2-phenylenediamines and aldehydes and its application to preparative-scale synthesis . Synthesis 2003 , 1683 .
  • Singh , M. P. ; Sasmal , S. ; Lu , W. ; Chatterjee , M. N. Synthetic utility of catalytic Fe(III)/Fe(II) redox cycling towards fused heterocycles: A facile access to substituted benzimidazole, bisbenzimidazole, and imidazopyridine derivatives . Synthesis 2000 , 1380 .
  • Trivedi , R. ; De , S. K. ; Gibbs , R. A. A convenient one-pot synthesis of 2-substituted benzimidazoles . J. Mol. Cat. A: Chem. 2005 , 245 , 8 .
  • Massimo , C. ; Francesco , E. ; Francesca , M. Ytterbium triflate–promoted synthesis of benzimidazole derivatives . Synlett 2004 , 1832 .
  • Itoh , T. ; Nagata , K. ; Ishikawa , H. ; Ohsawa , A. Synthesis of 2-arylbenzothiazoles and imidazoles using scandium triflate as a catalyst for both a ring closing and an oxidation step . Heterocycles 2004 , 63 , 2769 .
  • Ma , H. Q. ; Wang , Y. L. ; Wang J. Y. A simple KHSO4-promoted synthesis of 2-arylsubstituted benzimidazoles by oxidative condensation of aldehydes with o-phenylenediamine . Heterocycles 2006 , 68 , 1669 .
  • Ma , H. Q. ; Wang , Y. L. ; Li , J. P. ; Wang , J. Y Selective synthesis of 2-aryl-1-arylmethyl-1H-1,3-benzimidazoles promoted by ionic liquid. Heterocycles 2007, 71, 135.
  • Ahmad , S. ; Ali , M. Cellulose sulfuric acid as a bio-supported and recyclable solid acid catalyst for the one-pot, three-component synthesis of α-amino nitriles . Appl. Catal. A: Gen. 2007 , 331 , 149 .
  • Ahmad , S. ; Ali , M. ; Jafar , M. R. ; Ebrahim , S. Cellulose sulfuric acid–catalyzed one-pot, three-component synthesis of imidazoazines . Chem. Pharm. Bull. 2007 , 55 , 957 .
  • Ahmad , S. ; Abbas , R. ; Zahra , B. Sulfonated cellulose and starch: New biodegradable and renewable solid acid catalysts for efficient synthesis of quinolines . Catal. Commun. 2008 , 9 , 13 .
  • Venu Madhav , J. ; Thirupathi Reddy , Y. ; Narsimha Reddy , P. ; Nikhil Reddy , M. ; Suresh , K. ; Crooks , P. A. ; Rajitha , B. Cellulose sulfuric acid: An efficient biodegradable and recyclable solid acid catalyst for the one-pot synthesis of aryl-14H-dibenzo[a.j]xanthenes under solvent-free conditions . J. Mol. Catal. A 2009 , 304 , 85 – 87 .
  • Narsimha Reddy , P. ; Thirupathi Reddy , Y. ; Nikhil Reddy , M. ; Rajitha , B. ; Crooks , P. A. cellulose sulfuric acid: An efficient biodegradable and recyclable solid acid catalyst for the one-pot synthesis of 3,4-dihydropyrimidine-2(1H)-ones . Synth. Commun. 2009 , 39 , 1257 .
  • Suresh Kuarm , B. ; Venu Madhav , J. ; Vijaya Laxmi , S. ; Rajitha , B. ; Thirupathi Reddy , Y. ; Narsimha Reddy , P. ; Crooks , P. A. An expeditious Pechmann condensation by using biodegradable cellulose sulfuric acid as a solid acid catalyst . Synth. Commun. 2010 , 40 , 3358 .
  • Venu Madhav , J. ; Suresh Kuarm , B. ; Rajitha , B. Dipyridine copper chloride as a mild and efficient catalyst for the solid state-synthesis of 2-substituted benzimidazoles . Arkivoc 2008 , 13 , 145 – 150 .

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.