Jump to ContentJump to Main Navigation
Show Summary Details
More options …

Zeitschrift für Naturforschung B

A Journal of Chemical Sciences

12 Issues per year


IMPACT FACTOR 2017: 0.757

CiteScore 2017: 0.68

SCImago Journal Rank (SJR) 2017: 0.277
Source Normalized Impact per Paper (SNIP) 2017: 0.394

Online
ISSN
1865-7117
See all formats and pricing
More options …
Ahead of print

Issues

Three-component condensation reaction of various aldehydes, dimedone and malononitrile catalyzed by boric acid in water in comparison with multifunctional ionic liquids as green catalytic systems

Ardeshir Khazaei / Heidar Ali Alavi Nik / Ahmad Reza Moosavi-Zare
  • Corresponding author
  • Department of Chemistry, Sayyed Jamaleddin Asadabadi University, Asadabad, 6541861841, I.R. Iran
  • Email
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Hadis Afshar-Hezarkhani
  • Department of Chemistry, Sayyed Jamaleddin Asadabadi University, Asadabad, 6541861841, I.R. Iran
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
Published Online: 2018-09-06 | DOI: https://doi.org/10.1515/znb-2018-0101

Abstract

Triethanol ammonium acetate ([TEAH]+[OAc]) and triethanol ammonium formate ([TEAH]+[HCOO]) as multifunctional ionic liquids and catalysts were successfully applied for the preparation of tetrahydrobenzo[b]pyrans by the one-pot three-component condensation reaction of various aldehydes, dimedone and malononitrile under solvent-free conditions. These reactions were also tested using boric acid in water. In this catalytic system, by the reaction of water with boric acid, the hydronium ion caused by water separation can catalyze the reaction.

This article offers supplementary material which is provided at the end of the article.

Keywords: boric acid; multifunctional ionic liquid; solvent-free; tetrahydrobenzo[b]pyran; triethanol ammonium acetate; triethanol ammonium formate

References

  • [1]

    J. Zhu, H. Bienayme, Multicomponent Reactions, Wiley, Weinheim, 2005.Google Scholar

  • [2]

    A. Khazaei, M. A. Zolfigol, A. R. Moosavi-Zare, F. Abi, A. Zare, H. Kaveh, V. Khakyzadeh, M. Kazem-Rostami, A. Parhami, H. Torabi-Monfared, Tetrahedron 2011, 69, 212.Google Scholar

  • [3]

    M. A. Zolfigol, A. Khazaei, A. R. Moosavi-Zare, A. Zare, Z. Asgari, V. Khakyzadeh, A. Hasaninejad, Ind. Eng. Chem. Res. 2013, 19, 721.CrossrefGoogle Scholar

  • [4]

    A. Khazaei, M. A. Zolfigol, A. R. Moosavi-Zare, A. Zare, A. Parhami, A. Khalafi-Nezhad, Appl. Catal. A: General 2010, 386, 179.CrossrefGoogle Scholar

  • [5]

    M. A. Zolfigol, A. Khazaei, A. R. Moosavi-Zare, J. Afsar, V. Khakyzadeh, O. Khaledian, J. Chin. Chem. Soc. 2015, 62, 398.CrossrefGoogle Scholar

  • [6]

    G. Harichandran, S. D. Amalraj, P. Shanmugam, J. Iran. Chem. Soc. 2011, 8, 298.CrossrefGoogle Scholar

  • [7]

    B. V. Shitole, N. V. Shitole, G. K. Kakde, Org. Chem.: Indian J. 2015, 11, 283.Google Scholar

  • [8]

    H. Kiyani, F. Ghorbani, Res. Chem. Intermed. 2015, 41, 2653.CrossrefGoogle Scholar

  • [9]

    A. Kumar, D. Saxena, M. K. Gupta, RSC Adv. 2013, 3, 4610.CrossrefGoogle Scholar

  • [10]

    J. S. Yadav, M. K. Gupta, R. Jain, N. N. Yadav, B. V. Reddy, R. Subba, Monatsh. Chem. 2010, 141, 1001.CrossrefGoogle Scholar

  • [11]

    A. Khazaei, H. A. Alavi Nik, A. R. Moosavi-Zare, J. Chin. Chem. Soc. 2015, 62, 675.CrossrefGoogle Scholar

  • [12]

    A. R. Moosavi-Zare, H. Afshar-Hezarkhani, M. M. Rezaei, Polycyclic Aromat. Compd. 2017, 1.Google Scholar

  • [13]

    L. Bonsignore, G. Loy, D. Secci, A. Calignano, Eur. J. Med. Chem. 1993, 28, 517.CrossrefGoogle Scholar

  • [14]

    T. S. Jin, A. Q. Wang, F. Shi, L. S. Han, L. B. Liu, T. S. Li, ARKIVOC, 2006, xiv, 78.Google Scholar

  • [15]

    R. Hekmatshoar, S. Majedi, K. Bakhtiari, Catal. Commun. 2008, 9, 307.CrossrefGoogle Scholar

  • [16]

    S. Abdolmohammadi, S. Balalaie, Tetrahedron Lett. 2007, 48, 3299.CrossrefGoogle Scholar

  • [17]

    M. Seifi, H. Sheibani, Catal. Lett. 2008, 126, 275.CrossrefGoogle Scholar

  • [18]

    S. Balalaie, M. Bararjanian, A. M. Amani, B. Movassagh, Synlett 2006, 2, 263.Google Scholar

  • [19]

    A. R. Moosavi-Zare, M. A. Zolfigol, O. Khaledian, V. Khakyzadeh, M. D. Farahani, New J. Chem. 2014, 38, 2342.CrossrefGoogle Scholar

  • [20]

    T.-S. Jin, A.-Q. Wang, X. Wang, J.-S. Zhang, T.-S. Li, A. Clean, Synlett 2004, 5, 871.Google Scholar

  • [21]

    K. A. Undale, Y. K. Park, K. Park, D. H. Dagade, D. M. Pore, Synlett 2011, 6, 791.Google Scholar

  • [22]

    R. S. Bhosale, C. V. Magar, K. S. Solanke, S. B. Mane, S. S. Choudhary, R. P. Pawar, Synth. Commun. 2007, 37, 4353.CrossrefGoogle Scholar

  • [23]

    J. Zheng, Y.-Q. Li, Arch. Appl. Sci. Res. 2011, 3, 381.Google Scholar

  • [24]

    H. R. Shaterian, M. Arman, F. Rigi, J. Mol. Liq. 2011, 158, 145.CrossrefGoogle Scholar

About the article

Received: 2018-05-09

Accepted: 2018-08-10

Published Online: 2018-09-06


Citation Information: Zeitschrift für Naturforschung B, 20180101, ISSN (Online) 1865-7117, ISSN (Print) 0932-0776, DOI: https://doi.org/10.1515/znb-2018-0101.

Export Citation

©2018 Walter de Gruyter GmbH, Berlin/Boston.Get Permission

Supplementary Article Materials

Comments (0)

Please log in or register to comment.
Log in