Skip to main content
Log in

DABCO-promoted one-pot synthesis of heteroaryl-substituted benzenes and their biological evaluation

  • Original Research
  • Published:
Medicinal Chemistry Research Aims and scope Submit manuscript

Abstract

A simple and efficient one-pot synthesis of heteroaryl-substituted benzenes has been developed via cyclocondensation of vinylmalononitriles and ethylvinylcyanoacetates with heteroarylnitroolefines using diazabicyclo[2,2,2]octane as catalyst. The titled compounds were evaluated for their antitubercular, antibacterial and antifungal activities at various concentrations.

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

Access this article

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

Instant access to the full article PDF.

Scheme 1
Scheme 2
Scheme 3

Similar content being viewed by others

References

  • Asao N, Nogami T, Lee S, Yamamoto Y (2003) Lewis acid catalyzed benzannulation via unprecedented [4+2] cycloaddition of O-alkynyl(oxo)benzenes and enynals with alkynes. J Am Chem Soc 125:10921–10925

    Google Scholar 

  • Barun O, Nandi S, Panda K, Ila H, Junjappa H (2002) [4+2] Cyclo aromatization of 4-bis(methylthio)-3-butene-2-one with active methylene ketones: a simple and facile phenol annulation. J Org Chem 67:5398–5401

    Article  CAS  PubMed  Google Scholar 

  • Bonaga LVR, Zhang HC, Moretto AF, Ye H, Gauthier DA, Li J, Leo GC, Marynoff BE (2005) Synthesis of macrocycles via cobalt mediated [2+2+2] cycloadditions. J Am Chem Soc 127:3473–3485

    Article  CAS  PubMed  Google Scholar 

  • Cambau E, Truffot-Pernot C, Boulahbal F, Wichlacz C, Grosset J, Jarlier V (2000) Mycobacterial growth indicator tube versus the proportion method on Lowenstein-Jensen medium for antibiotic susceptibility testing Mycobacterium tuberculosis. Eur J Clin Microbiol Infect Dis 12:938–942

    Article  Google Scholar 

  • Chen Z, Ding K, Su W (2011) Basic ionic liquid as catalyst for the efficient and green synthesis of 2-amino-3-nitrobenzonitriles in ethanol. Synth Commun 41(10):1410–1420

    Article  CAS  Google Scholar 

  • Hassan J, Sevignon M, Gozzi C, Schulz E, Lemaire M (2002) Aryl−aryl bond formation one century after the discovery of the Ullmann reaction. Chem Rev 102:1359–1470

    Article  CAS  PubMed  Google Scholar 

  • Kim N, Park DY, Lee KY, Saravanan G (2008) Synthesis of poly-substituted phenols from Baylis–Hillman adducts and 1,3-dinitroalkanes. Bull Korean Chem Soc 29:701–704

    Article  Google Scholar 

  • Krishna NS, Satish KS (2010) An efficient momo-mode MW controlled multicomponent synthesis of poly substituted benzenes under solvent free conditions. Ind J Chem 49(B):826–829

    Google Scholar 

  • Mehta AG, Patel KH (2006) Synthesis and antifungal activity of azetidinone and thiazolidinone derivatives of 2-amino-6-(2-naphthaleneyl) thiazolo[3,2-d]thiadiazole. Eur J Chem 3:267–273

    Google Scholar 

  • Milart P, Wilamowski J, Sepiol JJ (1998) Synthesis of di- and triamino-1,1′,-3′,1″-terphynylidene and arylidene malonodinitriles. Tetrahedron 54:15643–15656

    Article  CAS  Google Scholar 

  • Olah G (1963) Friedal–Crafts and related reactions, vol I–IV. Wiley Interscience, New York

    Google Scholar 

  • Saito S, Yamamoto Y (2000) Recent advances in the transition metal catalyzed region selective approaches to poly substituted benzene derivatives. Chem Rev 100:2901–2916

    Article  CAS  PubMed  Google Scholar 

  • Jain S, Neelaiah B, Jetti SR, Shah H, Surya PD (2012a) Synthesis, antitubercular and antifungal activities of heteroaryl substituted oxiranes derived from Baylis–Hillman adducts. Med Chem Res 21(10):2744–2748

    Article  CAS  Google Scholar 

  • Jain S, Keshwal BS, Rajguru D (2012b) A clean and efficient l-proline-catalyzed synthesis of polysubstituted benzenes in the ionic liquid 1-butyl-3-methylimidazolium hexafluorophosphate. J Serb Chem Soc 77(10):1345–1352

    Article  CAS  Google Scholar 

  • Jain S, Keshwal BS, Rajguru D, Bhagwat VW (2012c) A simple and clean synthesis of polysubstituted 2,6-dicyanoanilines catalyzed by KF/alumina. J Korean Chem Soc 56(6):712–715

    Article  CAS  Google Scholar 

  • Jain S, Paliwal PK, Babu GN, Anjna B (2013) DABCO promoted one-pot synthesis of dihydropyrano(c)chromene and pyrano[2,3-d]pyrimidine derivatives and their biological activities. J Saudi Chem Soc. http://dx.doi.org/10.1016/j.jscs.2011.10.023

  • Trost BM (1991) The atom economy—a search for synthetic efficiency. Science 254:1471–1477

    Article  CAS  PubMed  Google Scholar 

  • Warshakoon NC, Sheville J, Bhatt RT, Ji W, Mendez-Andino JL, Meyers KM, Kim N, Wos JA, Mitchell C, Paris JL, Pinney BB, Riezs O, Hu XE (2006) Design and synthesis of substituted quinolines as novel and selective melanin concentrating hormone antagonists as anti-obesity agents. Bioorg Med Chem Lett 16:5207–5211

    Article  CAS  PubMed  Google Scholar 

  • Weike S, Ding K, Chen Z (2009) Cu(oTf)2/Et3N promoted cyclocondensation of activated α-methylene alkenes and nitro olefins: a novel one pot synthesis of poly substituted benzenes. Tetrahedron Lett 50:636–639

    Article  Google Scholar 

  • Xi Z, Sato K, Gao Y, Lu J, Takahashi T (2003) Unprecedented double C–C bond cleavage of cyclopentadienyl ligand. J Am Chem Soc 125:9568–9569

    Article  CAS  PubMed  Google Scholar 

  • Xin X, Wang Y, Lin Y, Duan H (2010) A facile and efficient one-pot synthesis of polysubstituted benzenes in guanidinium ionic liquids. Green Chem 12:893–898

    Article  CAS  Google Scholar 

  • Xue D, Jie L, Zhang Z-T, Deng j-G (2007) Efficient method for the synthesis of polysubstituted benzenes by one-pot tandem reaction of vinyl malononitriles and nitro olefins. J Org Chem 72:5443–5445

    Article  CAS  PubMed  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to G. Neelaiah Babu.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Babu, G.N., Ayalew, H.M. & Jain, S. DABCO-promoted one-pot synthesis of heteroaryl-substituted benzenes and their biological evaluation. Med Chem Res 23, 2608–2614 (2014). https://doi.org/10.1007/s00044-013-0857-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00044-013-0857-0

Keywords

Navigation