Skip to main content
SpringerLink
Log in

Mild and Efficient Synthesis of Benzoxazoles, Benzothiazoles, Benzimidazoles, and Oxazolo[4,5-b]pyridines Catalyzed by Bi(III) Salts Under Solvent-Free Conditions

  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Summary.

A series of benzoxazoles, benzothiazoles, benzimidazoles, and oxazolo[4,5-b]pyridines was efficiently synthesized from the reactions of o-aminophenols, o-aminothiophenol, o-phenylenediamines, and 2-amino-3-hydroxypyridine with orthoesters in the presence of catalytic amounts of Bi(III) salts, such as Bi(TFA)3, Bi(OTf)3, and BiOClO4 · xH2O under solvent-free conditions. The remarkable features of this new protocol are high conversion, very short reaction times, cleaner reaction profiles under solvent-free conditions, straightforward procedure, and use of relatively non-toxic catalysts.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  • a) Denny WA, Rewcastle GW, Baguley B (1990) J Med Chem 33: 814; b) Kondo J, Suzuki N, Imaoka T, Kawasaki T, Nakanishi A, Kawahara Y (1994) Anal Sci 10: 17; c) Zhao M, Samoc M, Prasad PN, Reinhardt BA, Sinky M (1992) Chem Mater 2: 670; d) Cassidy PE (1980) Thermally Stable Polymers, Marcel Dekker, New York; e) Lin S, Yang L (2005) Tetrahedron Lett 46: 4315; f) Mortimer CG, Wells G, Crochard J-P, Stone EL, Bradshaw TD, Stevens MFG, Westwell AD (2006) J Med Chem 49: 179; g) Chen C, Chen Y-J (2004) Tetrahedron Lett 45: 113; h) Frachy G; Crestini C, Berini R, Salidino R, Micione E (1994) Heterocycles 38: 2621

  • a) Kobayashi J, Madono T, Shigemori H (1995) Tetrahedron Lett 36: 5589; b) Rodriguez AD, Ramirez C, Rodriguez II, Gonzales E (1999) Org Lett 1: 527; c) Rodriguez II, Rodriguez AD (2003) J Nat Prod 66: 855; d) Ueki M, Ueno K, Miyadoh S, Abe K, Shibata K, Taniguchi M, Oi S (1993) J Antibiot 46: 1089; e) Paramashivappa R, Kumar PP, Subba Rao PV, Srinivasa Rao A (2003) Bioorg Med Chem Lett 13: 657; f) Koči J, Klimešová V, Waisser K, Kaustová J, Dahse H-M, Möllmann U (2002) Bioorg Med Chem Lett 12: 3275; g) Mann J, Baron A, Opoku-Boahen Y, Johansson E, Parkinson G, Kelland LR, Neidle S (2001) J Med Chem 44: 138; h) Craigo WA, LeSueur BW, Skibo EB (1999) J Med Chem 42: 3324

  • I Yildiz-Oren I Yalcin E Aki-Sener N Ucarturk (2004) Eur J Med Chem 39 291 Occurrence Handle10.1016/j.ejmech.2003.11.014 Occurrence Handle1:CAS:528:DC%2BD2cXislWjt7Y%3D

    Article  CAS  Google Scholar 

  • X Song BS Vig PL Lorenzi JC Drach LB Townsend GL Amidon (2005) J Med Chem 48 1274 Occurrence Handle10.1021/jm049450i Occurrence Handle1:CAS:528:DC%2BD2MXosFWmuw%3D%3D

    Article  CAS  Google Scholar 

  • M Yamato (1992) J Pharm Soc Jpn 112 81 Occurrence Handle1:CAS:528:DyaK38Xit1Onsbs%3D

    CAS  Google Scholar 

  • a) Kumar D, Jacob MR, Reynolds MB, Kerwin SM (2002) Bioorg Med Chem 10: 3997; b) DeLuca MR, Kerwin SM (1997) Tetrahedron Lett 38: 199; c) Sato S, Kajiura T, Noguchi M, Takehana K, Kobayasho T, Tsuji T (2001) J Antibiot 54: 102; d) Ueki M, Shibata K, Taniguchi M (1998) J Antibiot 51: 883

  • DA Evans CE Sacks WA Kleschick TR Taber (1979) J Am Chem Soc 101 6789 Occurrence Handle10.1021/ja00516a069 Occurrence Handle1:CAS:528:DyaL3cXlvVKlsA%3D%3D

    Article  CAS  Google Scholar 

  • a) Bywater WG, Coleman WR, Kamm O, Merritt HH (1945) J Am Chem Soc 67: 905; b) Benazzouz A, Boraud T, Dubédat P, Boireau A, Stutzmann J-M, Gross C (1995) Eur J Pharmacol 284: 299

    Google Scholar 

  • a) Grimmett MR (1996) In: Katritzky AR, Rees CW, Scriven EFV (eds) Comprehensive Heterocyclic Chemistry II, vol. 3, Elsevier Science Ltd, Oxford; b) Grimmett MR (1997) Imidazole and Benzimidazole Synthesis, Academic Press, San Diego

  • A Figge HJ Altenbach DJ Brauer P Tielmann (2002) Tetrahedron: Asymmetry 13 137 Occurrence Handle10.1016/S0957-4166(02)00079-4 Occurrence Handle1:CAS:528:DC%2BD38XitlWhtLo%3D

    Article  CAS  Google Scholar 

  • a) Alcalde E, Dinarés I, Pérez-García L, Roca T (1992) Synthesis 395; b) So Y-H, Heeschen JP (1997) J Org Chem 62: 3552; c) Heuser S, Keenan M, Weichert AG (2005) Tetrahedron Lett 46: 9001

  • a) Pottorf RS, Chadha NK, Katkevics M, Ozola V, Suna E, Ghane H, Regberg T, Player MR (2003) Tetrahedron Lett 44: 175; b) Nadaf RN, Siddiqui SA, Daniel T, Lahoti RJ, Srinivasan KV (2004) J Mol Catal A: Chem 214: 155

    Google Scholar 

  • DW Hein RJ Alheim JJ Leavitt (1957) J Am Chem Soc 79 427 Occurrence Handle10.1021/ja01559a053 Occurrence Handle1:CAS:528:DyaG2sXjsVyiuw%3D%3D

    Article  CAS  Google Scholar 

  • a) Villemin D, Hammadi M, Martin B (1996) Synth Commun 26: 2895; b) Doise M, Dennin F, Blondeau D, Sliwa H (1990) Tetrahedron Lett 31: 1155; c) Jenkins GL, Knevel AM, Davis CS (1961) J Org Chem 26: 274

  • Terashima M, Ishii M (1982) Synthesis 484

  • a) Chakraborti AK, Rudrawar S, Kaur G, Sharma L (2004) Synlett 1533; b) Dolbier Jr WR, Burkholder CR, Médebielle M (1999) J Fluorine Chem 95: 127

  • a) Hari A, Karan C, Rodrigues WC, Miller BL (2001) J Org Chem 66: 991; b) Beaulieu PL, Haché B, Von Moos E (2003) Synthesis 1683; c) Curini M, Epifano F, Montanari F, Rosati O, Taccone S (2004) Synlett 1832; d) Gogoi P, Konwar D (2006) Tetrahedron Lett 47: 79; e) Trivedi R, De SK, Gibbs RA (2006) J Mol Catal A: Chem 245: 8; f) Navarrete-Vázquez G, Moreno-Diaz H, Aguirre-Crespo F, León-Rivera I, Villalobos-Molina R, Muñoz-Muñiz O, Estrada-Soto S (2006) Bioorg Med Chem Lett 16: 4169; g) Lee CL, Lam Y, Lee S-Y (2001) Tetrahedron Lett 42: 109

  • GV Boyd (1984) NoChapterTitle AR Katritzky CW Rees KT Potts (Eds) Comprehensive Heterocyclic Chemistry Pergamon Press New York 177

    Google Scholar 

  • X-Z Bu Z-S Huang M Zhang L Ma G-W Xiao L-Q Gu (2001) Tetrahedron Lett 42 5737 Occurrence Handle10.1016/S0040-4039(01)01034-6 Occurrence Handle1:CAS:528:DC%2BD3MXlsFOlt7Y%3D

    Article  CAS  Google Scholar 

  • BM Bhawal SP Mayabhate AP Likhite ARAS Deshmukh (1995) Synth Commun 25 3315 Occurrence Handle1:CAS:528:DyaK2MXotFaiu7k%3D

    CAS  Google Scholar 

  • Y Chen DX Zeng (2004) J Org Chem 69 5037 Occurrence Handle10.1021/jo049565u Occurrence Handle1:CAS:528:DC%2BD2cXltVCnsbc%3D

    Article  CAS  Google Scholar 

  • a) Suzuki H, Ikegami T, Matano Y (1997) Synthesis 249; b) Reglinski J (1998) In: Norman NC (ed) Chemistry of Arsenic, Antimony and Bismuth, Balackie Academic and Professional, New York; c) Anderson AM, Blazek JM, Garg P, Payne BJ, Mohan RS (2000) Tetrahedron Lett 41: 1527; d) Leonard NM, Wieland LC, Mohan RS (2002) Tetrahedron 58: 8373; e) Chakraborti AK, Shivani GR (2003) Synlett 1805; f) Sabitha G, Venkata Reddy E, Swapna R, Mallikarjun Reddy N, Yadav JS (2004) Synlett 1276; g) Yadav JS, Reddy BVS, Premalatha K (2004) Synlett 963; h) Gosh R, Maiti S, Chakraborty A (2005) Synlett 115; i) Sreedhar B, Swapna V, Sridhar C (2005) Catal Commun 6: 293; j) Ollevier T, Mwene-Mbeja TM (2006) Tetrahedron Lett 47: 4051; k) Fu H, Zhang L, Yao W, Zhu Y (2006) Appl Catal B: Env 66: 100; l) Van Well WJM, Le MT, Schiødt NC, Hoste S, Stoltze P (2006) J Mol Catal A: Chem 256: 1; m) Sparks DE, Patterson PM, Jacobs G, Dogimont N, Tackett A, Crocker M (2006) Appl Catal B: Env 65: 44

  • a) Irving Sax N, Lewis RJ (1988) Dangerous Properties of Industrial Materials, Van Nostrand Reinhold, New York, p 522; b) Wormser U, Nir I (1994) In: Patai S (ed) The Chemistry of Organic Arsenic, Antimony and Bismuth Compounds, Wiley, New York, p 715

  • a) Firouzabadi H, Mohammadpoor-Baltork I, Kolagar S (2001) Synth Commun 31: 905; b) Mohammadpoor-Baltork I, Khosropour AR (2001) Molecules 996; c) Mohammadpoor-Baltork I, Khosropour AR, Aliyan H (2001) Synth Commun 31: 3411; d) Mohammadpoor-Baltork I, Khosropour AR, Aliyan H (2001) J Chem Res (S) 280; e) Mohammadpoor-Baltork I, Aliyan H, Khosropour AR (2001) Tetrahedron 57: 5851; f) Mohammadpoor-Baltork I, Khosropour AR (2002) Monatsh Chem 133: 189; g) Mohammadpoor-Baltork I, Kharamesh B, Kolagar S (2002) Synth Commun 32: 1633; h) Mohammadpoor-Baltork I, Khodaei MM, Nikoofar K (2003) Tetrahedron Lett 44: 591; i) Mohammadpoor-Baltork I, Khosropour AR, Hojati SF (2005) Synlett 2747; j) Khosropour AR, Mohammadpoor-Baltork I, Ghorbankhani H (2006) Catal Commun 7: 713; k) Khosropour AR, Mohammadpoor-Baltork I, Ghorbankhani H (2006) Tetrahedron Lett 47: 3561; l) Mohammadpoor-Baltork I, Memarian HR, Khosropour AR, Nikoofar K (2006) Heterocycles 68: 1837

  • a) Sam J, Plampin JN (1964) J Pharm Sci 53: 538; b) Roussos M, Lecomte J (1962) Ger 1 124: 499, (1963) Chem Abstr 57: 9858g; c) Raban M, Chang H, Craine L, Hortelano E (1985) J Org Chem 50: 2205; d) Wang H, Partch RE, Li Y (1997) J Org Chem 62: 5222; e) Aldrich Catalogue Handbook of Fine Chemicals (2000–2001); f) Kato H, Shiba T, Kitajima E, Kiyosawa T (1976) J Chem Soc Perkin Trans I 863; g) Takahashi T, Yoneda F (1957) Pharm Bull 5: 350

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Isfahan University, Isfahan, Iran

    Iraj Mohammadpoor-Baltork, Ahmad R. Khosropour & Seyedeh F. Hojati

Authors
  1. Iraj Mohammadpoor-Baltork
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Ahmad R. Khosropour
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Seyedeh F. Hojati
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Iraj Mohammadpoor-Baltork.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Mohammadpoor-Baltork, I., Khosropour, A. & Hojati, S. Mild and Efficient Synthesis of Benzoxazoles, Benzothiazoles, Benzimidazoles, and Oxazolo[4,5-b]pyridines Catalyzed by Bi(III) Salts Under Solvent-Free Conditions. Monatsh. Chem. 138, 663–667 (2007). https://doi.org/10.1007/s00706-007-0655-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-007-0655-9

Search

Navigation